WO2023242192A1 - Syrup containing high concentration of cellooligosaccharides - Google Patents

Abstract

The invention relates to a syrup comprising one or more cellooligosaccharides in dissolved form at an overall content of at least 10 wt.-%, preferably at least 12.5 wt.-%, more preferably at least 50 wt.-%, relative to the total weight of the syrup. Preferably, the cellooligosaccharides that are contained in the syrup in dissolved form are predominantly cellotriose and/or cellotetraose, i.e. among all cellooligosac- charides that are contained in the syrup in dissolved form, cellotriose and/or cellotetraose are the individual cellooligosaccharides preferably having the highest content compared to each of the other cellooligosaccharides that are contained in the syrup in dissolved form. The syrup is preferably oversaturated with respect to the one or more cellooligosaccharides in dissolved form and particularly useful as additive for foodstuffs, beverages, feed or cosmetic compositions.

Description

Syrup containing high concentration of cellooligosaccharides

[0001] Priority is claimed of European patent application no. 22179181.7 that was filed on June 15, 2022.

[0002] The invention relates to a syrup comprising one or more cellooligosaccharides in dissolved form at an overall content of at least 10 wt.-%, preferably at least 12.5 wt.-%, more preferably at least 50 wt.- %, relative to the total weight of the syrup. Preferably, the cellooligosaccharides that are contained in the syrup in dissolved form are predominantly cellotriose and/or cellotetraose, i.e. among all cellooligosaccharides that are contained in the syrup in dissolved form, cellotriose and/or cellotetraose are the individual cellooligosaccharides preferably having the highest content compared to each of the other cellooligosaccharides that are contained in the syrup in dissolved form. The syrup is preferably oversaturated with respect to the one or more cellooligosaccharides in dissolved form and particularly useful as additive for foodstuffs, beverages, feed or cosmetic compositions.

[0003] Several non-digestible oligosaccharides can promote immune modulatory health effects by positively influencing the microbiome composition of the gut (prebiotics). In this regard, cellooligosaccharides have attracted widespread attention as low-caloric fibers, potential prebiotics, additives in pharmaceutical products, and the like.

[0004] Cellooligosaccharides are composed of D-glucose monomers that are linked by a [3-1,4-glyco- sidic bond. Human digestive enzymes are not capable of degrading cellooligosaccharides. Cellobiose, the [3-1,4-linked disaccharide of D-glucose, cannot be digested by human digestive enzymes either. According to nutritional regulations and legislation (e.g. FDA labeling requirements for foods under the Federal Food, Drug, and Cosmetic Act; EFSA labeling requirements for foods in accordance with the Food Labelling Information System (FLIS), and the like), cellobiose is typically to be declared as "carbohydrate", whereas cellooligosaccharides such as cellotriose or cellotetraose are to be declared as "fiber" .

[0005] There is thus a demand for cellooligosaccharide preparations that can be used as additives for the preparation of foodstuffs, beverages, feed, cosmetic compositions and further products.

[0006] As cellooligosaccharides can advantageously evolve their beneficial effects, e.g. influence the microbiome composition of the gut, when they are provided in aqueous solution but not in solid form, the cellooligosaccharide preparations should be aqueous and contain considerable amounts of cellooligosaccharides in dissolved form. Further, as the cellooligosaccharide preparations should be useful as additives for the preparation of foodstuffs, beverages, feed, cosmetic compositions and further products, they should contain the cellooligosaccharide at high concentrations. When the cellooligosaccharide concentrations were low, the remaining constituents of the cellooligosaccharide preparations such as water would have an undesirable diluting effect on the foodstuffs, beverages, feed, cosmetic compositions and further products to be prepared.

[0007] Cellooligosaccharides may be obtained either by controlled enzymatic degradation of cellulose, or by bottom-up synthesis e.g. from glucose.

[0008] JP-H 05 317 073 A relates to a method for obtaining a cellooligosaccharide by hydrolyzing a cellulose raw material rich in amorphous cellulose with cellulase in the presence of lignin while suppressing the inhibition of the hydrolysis reaction.

[0009] US 2004 0217063 Al relates to a process for preparing cellodextrins by cellulose hydrolysis using mixed concentrated hydrochloric acid and sulfuric acid. Cellulose is rapidly and completely dissolved to produce a high cellodextrin yield. Acetone is used as organic solvent for precipitating cellodextrins from the mixed acid hydrolyzate. Cellodextrins are resuspended in water and separated using ion exchange.

[0010] US 2007 0207108 Al relates to a process of producing cellooligosaccharide, comprising enzymatically decomposing, in the presence of cellulase, a water-insoluble natural cellulosic material having an average degree of polymerization not greater than 700, an average particle size not greater than 100. [0011] US 2009 0232892 Al relates to a cellooligosaccharide composition comprising, as the main ingredient, at least one cellooligosaccharide selected from the group consisting of cellobiose, cellotriose, cellotetraose, cellopentaose and cellohexaose, which is in the powdery form having an average U/D value of 3.0 or lower, a bulk density of 0.80 g/mU or lower and an angle of repose of 60° or lower.

[0012] WO 2016 038142 Al relates to a process for the enzymatic preparation of a product glucoside, preferably cellobiose, and of a co-product, preferably fructose, from an educt glucoside, preferably sucrose.

[0013] US 2018 0303120 Al relates to a food composition comprising a cellodextrin material, wherein the cellodextrin material comprises a principal cellodextrin with a degree of polymerization (DP) value of at least 4.

[0014] US 2018 0362669 Al relates to a method of manufacturing a cellooligosaccharide containing an oligomer having a degree of polymerization of from 3 to 6.

[0015] WO 2019 211971 Al (EP 3 789 493 Al) relates to a cellooligosaccharide production method. In order to suppress cellooligosaccharides with a high degree of polymerization from occurring in the enzymatic synthesis of cellooligosaccharides, the production method involves a step in which a-glucose- 1 -phosphate, and at least one type of primer selected from the group consisting of glucose, cellobiose and alkylated glucose are reacted with cellodextrin phosphorylase in a mixed solvent that contains water and a water-soluble organic solvent.

[0016] US 2020 0299791 Al relates to the production of saccharides from an aqueous solution which solution comprises saccharides and by-products. [0017] Ch. Zhong et al., Biotechnology and Bioengineering, 2019;116:2146-2155 relates to product solubility control in cellooligosaccharide production by coupled cellobiose and cellodextrin phosphorylase.

[0018] P. Zhou et al., Applied Biochemistry and Biotechnology, 192, 600-615 (2020) report about simultaneous production of cellooligosaccharide and glucose monodecanoate from lignocellulose by enzymatic esterification.

[0019] Z. Ubiparip et al., Applied Microbiology and Biotechnology (2020) 104:8327-8337 report about engineering of cellobiose phosphorylase for the defined synthesis of cellotriose.

[0020] S. Sun et al., Synthetic and Systems Biotechnology 6 (2021) 23-31 review structure, catalytic mechanisms and directed evolution of disaccharide phosphorylases.

[0021] Cellooligosaccharides are sparingly soluble in water and solubility decreases with degree of polymerization (DP). Cellobiose has been reported to have a water solubility of about 1. 11E+05 mg/L at 15°C (https://chem.nlm.nih.gov/chemidplus/rn/528-50-7). At 20°C, a solubility in water of 177±1 g-L^-1 has been reported (J. Heng, Thesis, Worcester Polytechnic Institute, 2020, page 21).

[0022] The water solubilities and heats of solution of short chain cellulosic oligosaccharides have been investigated by J.B. Taylor, Trans. Faraday Soc., 1957,53, 1198-1203. The solid phases in equilibrium with the solutions at 20°C are not hydrated and the solubilities decrease rapidly as chain length increases. For cellulosic oligosaccharides the following water solubilities have been reported in the literature: cellotriose = 50 g-L ¹ (see Thermo Fisher Scientific, Alfa Aesar, catalog J67702); cellotetraose: 25 g-L ¹ (see https://www.chembk.com/en/chem/cellotetraose); and cellopentaose: 19 g-L ¹ (see https ://www.chemblink.com/products/2240-27-9.htm) .

[0023] Thus, due to the poor solubilities, syrups containing cellooligosaccharides in dissolved form at comparatively high concentrations cannot be prepared by dissolving solid, e.g. crystalline or partially crystalline cellooligosaccharides in water.

[0024] Saturated aqueous solutions of cellooligosaccharides can be prepared from such crystalline or partially crystalline cellooligosaccharides. However, such compositions have rather low concentrations of the cellooligosaccharides. Further, when such compositions are used in the preparation of foodstuff or beverages, it has been reported that consumers complain about a "sandy", "gritty", "sabulous" or "frizzy" mouth feel, which is obviously due to crystallites of undissolved material.

[0025] There is a demand for aqueous compositions (syrups) containing cellooligosaccharides that have advantages compared to the compositions of the prior art. The aqueous compositions should contain cellooligosaccharides in dissolved form at high concentrations. Consumer compliance should be improved. The content of other saccharides (e.g. monosaccharides such as glucose, fructose; disaccharides such as sucrose, cellobiose) and potential impurities (e.g. glycerol, glucose- 1 -phosphate) should be low. The aqueous compositions should be edible and satisfy regulatory requirements. The cellooligosaccharides predominantly contained in the aqueous compositions should be cellotriose and/or cellotetraose, i.e. wherein among all cellooligosaccharides that are contained in the syrup in dissolved form, cellotriose and/or cellotetraose should be the individual cellooligosaccharides having the highest content compared to each of the other cellooligosaccharides that are contained in the syrup in dissolved form. The aqueous compositions should be obtainable in an economic manner from inexpensive starting materials. Initial yields of cellotriose or cellotetraose should be high and purification procedures, if any, should not significantly deteriorate the overall economic balance of the preparation procedure.

[0026] It is an object of the invention to provide improved aqueous compositions that contain cellooligosaccharides at comparatively high concentrations and are useful for preparing foodstuffs, beverages, feed or cosmetic compositions.

[0027] This object has been achieved by the subject-matter of the patent claims.

[0028] It has been found that when cellooligosaccharide syrups are prepared by bottom-up synthesis reacting glucose- 1 -phosphate with glucose or cellobiose as starting material in the presence of suitable enzymes, the reaction conditions may be modified such that reaction solutions are obtained containing considerable yields of cellotriose and/or cellotetraose at satisfactory conversion rates. Thus, concentrations of cellobiose may be kept comparatively low and formation of higher cellooligosaccharides such as cellopentaose, cellohexaose and the like can be suppressed.

[0029] Further, it has been surprisingly found that such reaction solutions, optionally after purification, may subsequently be evaporated thereby obtaining syrups that have high solids content, e.g. of 80 wt.- % and even more, and that do not show precipitation of the cellooligosaccharides. Thus, evaporation of such reaction solutions allows for obtaining syrups that are highly oversaturated with respect to the cellooligosaccharides and that remain in solution with excellent storage stabilities.

[0030] Due to the poor solubility of cellooligosaccharides, for thermodynamic reasons, such concentrations of the cellooligosaccharides in solution cannot be obtained by dissolving a corresponding amount solid cellooligosaccharides in a corresponding amount of water.

[0031] Further, it is believed that such concentrations of the cellooligosaccharides in solution cannot be obtained by evaporating reaction solutions that are obtained on the basis of other synthetic concepts, e.g. by controlled enzymatic degradation of cellulose. It rather appears that only bottom-up synthesis reacting glucose- 1 -phosphate with glucose or cellobiose as starting material in the presence of suitable enzymes provides reaction solutions that upon evaporation provide highly oversaturated solutions of cellooligosaccharides, particularly cellotriose and/or cellotetraose.

[0032] Still further, it has been surprisingly found that the thus obtained syrups may be advantageously used for preparing foodstuffs, beverages, feed or cosmetic compositions having improved consumer compliance.

[0033] A first aspect of the invention relates to a syrup comprising one or more cellooligosaccharides in dissolved form at an overall content of at least 10 wt.-%, preferably at least 12.5 wt.-%, more preferably at least 50 wt.-%, relative to the total weight of the syrup. [0034] For the purpose of the specification "A and/or B" means (i) only A but not B, or (ii) only B but not A, or (iii) both A as well as B.

[0035] Preferably, the cellooligosaccharides that are contained in the syrup in dissolved form are predominantly cellotriose and/or cellotetraose. For the purpose of the specification, in this context "predominant" or "predominantly" means that among all cellooligosaccharides that are contained in the syrup in dissolved form, the cellooligosaccharide(s) referred to, e.g. "cellotriose and/or cellotetraose" , are the individual cellooligosaccharides having the highest content compared to each of the other cellooligosaccharides that are contained in the syrup in dissolved form.

[0036] When e.g. "cellotriose and/or cellotetraose" are the predominant cellooligosaccharide(s), (i) the content of cellotriose alone is higher compared to each of the other cellooligosaccharides that are contained in the syrup in dissolved form, e.g. also compared to cellotetraose; or (ii) the content of cellotetraose alone is higher compared to each of the other cellooligosaccharides that are contained in the syrup in dissolved form, e.g. also compared to cellotriose; or (iii) the individual content of both cellotriose and of cellotetraose is higher compared to each of the other cellooligosaccharides that are contained in the syrup in dissolved form, whereas the relative content of cellotriose to cellotetraose is not relevant, i.e. it does not matter whether the content of cellotriose is higher than the content of cellotetraose, or vice versa.

[0037] For the purpose of the specification, unless expressly stated otherwise, a "syrup" is an aqueous composition containing a high concentration (at least 10 wt.-%, preferably at least 12.5 wt.-%) of one or more cellooligosaccharides in solution, i.e. in dissolved form. While besides the one or more cellooligosaccharides and water the syrup may contain further constituents, the one or more cellooligosaccharides and the water typically constitute the major components of the syrup. The content of constituents other than the one or more cellooligosaccharides and the water is typically at most 30 wt.-%, preferably at most 25 wt.-%, more preferably at most 20 wt.-%, still more preferably at most 15 wt.-%, even more preferably at most 10 wt.-%, most preferably at most 7.5 wt.-%, and in particular at most 5 wt.-%, in each case relative to the total weight of the syrup.

[0038] The syrup according to the invention comprises one or more cellooligosaccharides "in dissolved form" at an "overall content" of the one or more cellooligosaccharides of at least 10 wt.-%, relative to the total weight of the syrup.

[0039] The "overall content" refers to the sum of the individual contents of the one or more cellooligosaccharides that are present in dissolved form.

[0040] As the overall content of the one or more cellooligosaccharides amounting to at least 10 wt.-%, preferably at least 12.5 wt.-% relative to the total weight of the syrup, refers to those one or more cellooligosaccharides that are present "in dissolved form", the overall content corresponds to the overall concentration of the one or more cellooligosaccharides in aqueous solution. [0041] It is contemplated that the syrup according to the invention may additionally comprise one or more cellooligosaccharides in undissolved form, i.e. in suspension. However, any content of the one or more cellooligosaccharides in undissolved form is not encompassed by the definition of said overall content of the one or more cellooligosaccharides in dissolved form amounting to at least 10 wt.-%, relative to the total weight of the syrup.

[0042] Preferably, any potential hydrocolloids of the one or more cellooligosaccharides are encompassed by the definition of said overall content of the one or more cellooligosaccharides in dissolved form amounting to at least 10 wt.-%, preferably at least 12.5 wt.-% relative to the total weight of the syrup. Hydrocolloids may be distinguished from solutions using the Tyndall effect. Preferably, when a given composition is considered as suspension of the one or more cellooligosaccharides, the content of the one or more cellooligosaccharides that are contained "in dissolved form" is determined after microfiltration of the composition through a microfiltration membrane having a pore size of 0.2 pm. Such membranes are commercially available. The content of the one or more cellooligosaccharides after such ultrafiltration is considered to be present "in dissolved form" for the purposes of the specification.

[0043] For the purpose of the specification, unless expressly stated otherwise, all saccharides are preferably present in D-configuration (Fischer projection).

[0044] For the purpose of the specification, unless expressly stated otherwise, all physical properties such as solubility are determined at room temperature (23 °C), an air pressure of 1023 hPa and a relative humidity of 50% rh.

[0045] Cellooligosaccharides (also known as cellodextrins) are oligomers of (1^4)-linked [3-D-glu- cose, i.e. O-P-D-glucopyranosyl-(1^4)-[O-[3-D-glucopyranosyl-(1^4)-]n-D-glucose, wherein index n is from 3 to 10. In accordance with IUPAC Gold Book (https://goldbook.iupac.org/terms/view/O04282), "oligo" is a prefix used for compounds with a number of repeating units intermediate between those in monomers and those in high polymers. For the purpose of the specification, the limits are from 3 to 10 such that cellooligosaccharides of the following degree of polymerization (DP, index n) are to be con- sidered cellooligosaccharides:

DP3: cellotriose, CD3, DP7: celloheptaose, CD7,

DP4: cellotetraose, CD4, DP8: cellooctaose, CD8,

DP5: cellopentaose, CD5, DP9: cellononaose, CD9, and

DP6: cellohexaose, CD6, DP 10: cellodecaose, CD 10.

[0046] For the purpose of the specification, neither the disaccharide cellobiose (DP2) nor higher homologues with index n > 10 are to be considered cellooligosaccharides.

[0047] For the purpose of the specification, a "syrup" is an aqueous composition containing a comparatively high concentration of carbohydrates in dissolved form. Preferably, the syrup according to the invention is a solution, but not a suspension. [0048] For the purpose of the specification, unless expressly stated otherwise, all percentages are expressed as weight percent, and all contents and concentrations are related to the total weight of the syrup. For the purpose of the specification, "essentially no" means at most 1.0 wt.-%, preferably at most 0.5 wt.-%, more preferably at most 0.1 wt.-%, in each case relative to the total weight of the syrup.

[0049] For the purpose of the specification, unless expressly stated otherwise, a cellodextrin phosphorylase (CDP, EC 2.4.1.49) is an enzyme that catalyzes the chemical reaction of (l,4-beta-D-glucosyl)n + phosphate to (l,4-beta-D-glucosyl)n-l + alpha-D-glucose 1 -phosphate, and vice versa. Typically, the cellodextrin phosphorylase is unspecific with respect to the value of index n, i.e. the degree of polymerization.

[0050] For the purpose of the specification, unless expressly stated otherwise, a cellobiose phosphorylase (CBP, EC 2.4.1.20) is an enzyme that catalyzes the chemical reaction of cellobiose + phosphate to glucose + alpha-D-glucose 1 -phosphate, and vice versa. While a cellobiose phosphorylase may additionally also exhibit to a certain extent e.g. cellotriose phosphorylase activity and cellotetraose phosphorylase activity, it is typically not entirely unspecific with respect to the degree of polymerization.

[0051] For the purpose of the specification, unless expressly stated otherwise, a cellotriose phosphorylase is an enzyme that catalyzes the chemical reaction of cellotriose + phosphate to cellobiose + alphaD-glucose 1 -phosphate, and vice versa. While a cellotriose phosphorylase may additionally also exhibit to a certain extent e.g. cellobiose phosphorylase activity and cellotetraose phosphorylase activity, it is typically not entirely unspecific with respect to the degree of polymerization.

[0052] For the purpose of the specification, unless expressly stated otherwise, a cellotetraose phosphorylase is an enzyme that catalyzes the chemical reaction of cellotetraose + phosphate to cellotriose + alpha-D-glucose 1 -phosphate, and vice versa. While a cellotetraose phosphorylase may additionally also exhibit to a certain extent e.g. cellobiose phosphorylase activity and cellotriose phosphorylase activity, it is typically not entirely unspecific with respect to the degree of polymerization.

[0053] Preferably, the syrup according to the invention comprises essentially no undissolved cellooli- gosaccharides, preferably no undissolved material at all. Thus, preferably, the syrup according to the invention is not a suspension, but a solution that may potentially contain hydrocolloids.

[0054] Preferably, the syrup according to the invention is oversaturated with respect to the one or more cellooligosaccharides in dissolved form.

[0055] In preferred embodiments of the syrup according to the invention, the overall content of the one or more cellooligosaccharides is at least 15 wt.-%, preferably at least 20 wt.-%, more preferably at least 25 wt.-%, still more preferably at least 30 wt.-%, yet more preferably at least 35 wt.-%, even more preferably at least 40 wt.-%, most preferably at least 45 wt.-%, and in particular at least 50 wt.-%, in each case relative to the total weight of the syrup.

[0056] In preferred embodiments of the syrup according to the invention, the overall content of the one or more cellooligosaccharides is at least 52 wt.-%, preferably at least 54 wt.-%, more preferably at least 56 wt.-%, still more preferably at least 58 wt.-%, yet more preferably at least 60 wt.-%, even more preferably at least 62 wt.-%, most preferably at least 64 wt.-%, and in particular at least 66 wt.-%, in each case relative to the total weight of the syrup.

[0057] In preferred embodiments of the syrup according to the invention, the overall content of the one or more cellooligosaccharides is at least 68 wt.-%, still more preferably at least 70 wt.-%, yet more preferably at least 72 wt.-%, even more preferably at least 74 wt.-%, most preferably at least 76 wt.-%, and in particular at least 78 wt.-%, in each case relative to the total weight of the syrup.

[0058] The syrup according to the invention is characterized by a dry solids content. The dry solids content (DS) is the residual amount of all constituents that remain after full evaporation of all liquids.

[0059] Preferably, the syrup according to the invention has a dry solids content of at least 15 wt.-%, preferably at least 20 wt.-%, more preferably at least 25 wt.-%, still more preferably at least 30 wt.-%, yet more preferably at least 35 wt.-%, even more preferably at least 40 wt.-%, most preferably at least 45 wt.-%, and in particular at least 50 wt.-%, in each case relative to the total weight of the syrup.

[0060] In preferred embodiments of the syrup according to the invention, the dry solids content is at least 55 wt.-%, preferably at least 60 wt.-%, more preferably at least 65 wt.-%, still more preferably at least 70 wt.-%, yet more preferably at least 75 wt.-%, even more preferably at least 80 wt.-%, most preferably at least 82.5 wt.-%, and in particular at least 85 wt.-%, in each case relative to the total weight of the syrup.

[0061] While it is contemplated that the syrup according to the invention may contain additional solvents other than water, water is preferably the only liquid that is contained in the syrup.

[0062] Preferably, the syrup according to the invention has a water content of at least 5.0 wt.-%, or at least 10 wt.-%, or at least 15 wt.-%, in each case relative to the total weight of the syrup.

[0063] Preferably, the syrup according to the invention has a water content of at most 70 wt.-%, preferably at most 65 wt.-%, more preferably at most 60 wt.-%, still more preferably at most 55 wt.-%, yet more preferably at most 50 wt.-%, even more preferably at most 45 wt.-%, most preferably at most 40 wt.-%, and in particular at most 35 wt.-%, in each case relative to the total weight of the syrup.

[0064] Preferably, the syrup according to the invention has a water content of at most 30 wt.-%, preferably at most 28 wt.-%, more preferably at most 26 wt.-%, still more preferably at most 24 wt.-%, yet more preferably at most 22 wt.-%, even more preferably at most 20 wt.-%, most preferably at most 18 wt.-%, and in particular at most 16 wt.-%, in each case relative to the total weight of the syrup.

[0065] The pH value of the syrup according to the invention is not particularly limited. In preferred embodiments, the pH value of the syrup according to the invention is within the range of 7.0±2.0, or 6.0±2.0, or 5.0±2.0, or 4.0±2.0.

[0066] The syrup according to the invention may contain salts, i.e. cations and anions, such as alkali metal cations, alkaline earth metal cations, halogen anions, and the like. [0067] In preferred embodiments of the syrup according to the invention, the overall content of the one or more cellooligosaccharides amounts to at least 55 wt.-%, preferably at least 60 wt.-%, more preferably at least 65 wt.-%, still more preferably at least 70 wt.-%, yet more preferably at least 75 wt.-%, even more preferably at least 80 wt.-%, most preferably at least 85 wt.-%, and in particular at least 90 wt.-%, in each case relative to the dry solids content of the syrup.

[0068] In preferred embodiments of the syrup according to the invention, the overall content of the one or more cellooligosaccharides amounts to at least 92 wt.-%, preferably at least 93 wt.-%, more preferably at least 94 wt.-%, still more preferably at least 95 wt.-%, yet more preferably at least 96 wt.-%, even more preferably at least 97 wt.-%, most preferably at least 98 wt.-%, and in particular at least 99 wt.-%, in each case relative to the dry solids content of the syrup.

[0069] In preferred embodiments of the syrup according to the invention, the sum of the content of water and the overall content of the one or more cellooligosaccharides amounts to at least 55 wt.-%, preferably at least 60 wt.-%, more preferably at least 65 wt.-%, still more preferably at least 70 wt.-%, yet more preferably at least 75 wt.-%, even more preferably at least 80 wt.-%, most preferably at least 85 wt.-%, and in particular at least 90 wt.-%, in each case relative to the total weight of the syrup.

[0070] In preferred embodiments of the syrup according to the invention, the sum of the content of water and the overall content of the one or more cellooligosaccharides amounts to at least 92 wt.-%, preferably at least 93 wt.-%, more preferably at least 94 wt.-%, still more preferably at least 95 wt.-%, yet more preferably at least 96 wt.-%, even more preferably at least 97 wt.-%, most preferably at least 98 wt.-%, and in particular at least 99 wt.-%, in each case relative to the total weight of the syrup.

[0071] In preferred embodiments of the syrup according to the invention, the sum of the content of cellobiose and the overall content of the one or more cellooligosaccharides amounts to at least 55 wt.- %, preferably at least 60 wt.-%, more preferably at least 65 wt.-%, still more preferably at least 70 wt.- %, yet more preferably at least 75 wt.-%, even more preferably at least 80 wt.-%, most preferably at least 85 wt.-%, and in particular at least 90 wt.-%, in each case relative to the total weight of the syrup. [0072] In preferred embodiments of the syrup according to the invention, the sum of the content of water and the overall content of the one or more cellooligosaccharides amounts to at least 92 wt.-%, preferably at least 93 wt.-%, more preferably at least 94 wt.-%, still more preferably at least 95 wt.-%, yet more preferably at least 96 wt.-%, even more preferably at least 97 wt.-%, most preferably at least 98 wt.-%, and in particular at least 99 wt.-%, in each case relative to the total weight of the syrup.

[0073] Preferably, the syrup according to the invention contains cellobiose and cellotriose; preferably wherein the cellooligosaccharides that are contained in the syrup in dissolved form are predominantly cellobiose and/or cellotriose, i.e. among all cellooligosaccharides that are contained in the syrup in dissolved form, cellobiose and/or cellotriose are the individual cellooligosaccharides preferably having the highest content compared to each of the other cellooligosaccharides that are contained in the syrup in dissolved form. [0074] In preferred embodiments of the syrup according to the invention, the content of cellobiose is greater than the content of cellotriose.

[0075] In preferred embodiments of the syrup according to the invention, the content of cellotriose is greater than the content of cellobiose.

[0076] Preferably, the syrup according to the invention contains cellotriose and cellotetraose; preferably wherein the cellooligosaccharides that are contained in the syrup in dissolved form are predominantly cellotriose and/or cellotetraose, i.e. among all cellooligosaccharides that are contained in the syrup in dissolved form, cellotriose and/or cellotetraose are the individual cellooligosaccharides preferably having the highest content compared to each of the other cellooligosaccharides that are contained in the syrup in dissolved form.

[0077] In preferred embodiments of the syrup according to the invention, the content of cellotriose is greater than the content of cellotetraose.

[0078] In preferred embodiments of the syrup according to the invention, the content of cellotetraose is greater than the content of cellotriose.

[0079] Preferably, the syrup according to the invention contains cellobiose and cellotetraose.

[0080] In preferred embodiments of the syrup according to the invention, the content of cellobiose is greater than the content of cellotetraose.

[0081] In preferred embodiments of the syrup according to the invention, the content of cellotetraose is greater than the content of cellobiose.

[0082] Preferably, the syrup according to the invention contains cellotriose, wherein the content of cellotriose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.-%, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.- %, most preferably at least 35 wt.-%, and in particular at least 40 wt.-%, in each case relative to the total weight of the syrup.

[0083] Preferably, the syrup according to the invention contains cellotriose, wherein the content of cellotriose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.-%, in each case relative to the total weight of the syrup.

[0084] Preferably, the syrup according to the invention contains cellotriose, wherein the content of cellotriose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.-%, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.- %, most preferably at least 35 wt.-%, and in particular at least 40 wt.-%, in each case relative to the dry solids content of the syrup.

[0085] Preferably, the syrup according to the invention contains cellotriose, wherein the content of cellotriose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.-%, in each case relative to the dry solids content of the syrup.

[0086] Preferably, the syrup according to the invention contains cellotetraose, wherein the content of cellotetraose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.-%, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 35 wt.-%, and in particular at least 40 wt.-%, in each case relative to the total weight of the syrup.

[0087] Preferably, the syrup according to the invention contains cellotetraose, wherein the content of cellotetraose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.-%, in each case relative to the total weight of the syrup.

[0088] Preferably, the syrup according to the invention contains cellotetraose, wherein the content of cellotetraose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.-%, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 35 wt.-%, and in particular at least 40 wt.-%, in each case relative to the dry solids content of the syrup.

[0089] Preferably, the syrup according to the invention contains cellotetraose, wherein the content of cellotetraose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.-%, in each case relative to the dry solids content of the syrup.

[0090] Preferably, the syrup according to the invention contains cellotriose and cellotetraose, wherein the sum of the content of cellotriose and the content of cellotetraose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.-%, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 35 wt.-%, and in particular at least 40 wt.-%, in each case relative to the total weight of the syrup.

[0091] Preferably, the syrup according to the invention contains cellotriose and cellotetraose, wherein the sum of the content of cellotriose and the content of cellotetraose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.-%, in each case relative to the total weight of the syrup.

[0092] Preferably, the syrup according to the invention contains cellotriose and cellotetraose, wherein the sum of the content of cellotriose and the content of cellotetraose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.-%, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 35 wt.-%, and in particular at least 40 wt.-%, in each case relative to the dry solids content of the syrup.

[0093] Preferably, the syrup according to the invention contains cellotriose and cellotetraose, wherein the sum of the content of cellotriose and the content of cellotetraose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.-%, in each case relative to the dry solids content of the syrup.

[0094] Preferably, the syrup according to the invention contains cellopentaose, wherein the content of cellopentaose is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least

2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup.

[0095] Preferably, the syrup according to the invention contains cellopentaose, wherein the content of cellopentaose is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup.

[0096] Preferably, the syrup according to the invention contains essentially no cellopentaose.

[0097] Preferably, the syrup according to the invention contains cellohexaose, wherein the content of cellohexaose is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least

2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup.

[0098] Preferably, the syrup according to the invention contains cellohexaose, wherein the content of cellohexaose is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most

2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup.

[0099] Preferably, the syrup according to the invention contains essentially no cellohexaose.

[0100] Preferably, the syrup according to the invention contains essentially no celloheptaose, essentially no cellooctaose, essentially no cellononaose, and essentially no cellodecaose.

[0101] Preferably, the syrup according to the invention contains cellobiose, wherein the content of cellobiose is at least 2.5 wt.-%, preferably at least 5.0 wt.-%, more preferably at least 7.5 wt.-%, still more preferably at least 10 wt.-%, yet more preferably at least 12.5 wt.-%, even more preferably at least 15 wt.-%, most preferably at least 17.5 wt.-%, and in particular at least 20 wt.-%, in each case relative to the total weight of the syrup. [0102] Preferably, the syrup according to the invention contains cellobiose, wherein the content of cellobiose is at most 40 wt.-%, preferably at most 35 wt.-%, more preferably at most 30 wt.-%, still more preferably at most 25 wt.-%, yet more preferably at most 20 wt.-%, even more preferably at most 15 wt.-%, most preferably at most 10 wt.-%, and in particular at most 5.0 wt.-%, in each case relative to the total weight of the syrup.

[0103] Preferably, the syrup according to the invention contains essentially no cellobiose.

[0104] Preferably, the syrup according to the invention contains sucrose, wherein the content of sucrose is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup.

[0105] Preferably, the syrup according to the invention contains sucrose, wherein the content of sucrose is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup.

[0106] Preferably, the syrup according to the invention contains essentially no sucrose.

[0107] Preferably, the syrup according to the invention contains glucose, wherein the content of glucose is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup.

[0108] Preferably, the syrup according to the invention contains glucose, wherein the content of glucose is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup.

[0109] Preferably, the syrup according to the invention contains essentially no glucose.

[0110] Preferably, the syrup according to the invention contains glucose- 1 -phosphate, wherein the content of glucose- 1 -phosphate is at least 0. 1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup.

[0111] Preferably, the syrup according to the invention contains glucose- 1 -phosphate, wherein the content of glucose- 1 -phosphate is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup.

[0112] Preferably, the syrup according to the invention contains essentially no glucose- 1 -phosphate.

[0113] Preferably, the syrup according to the invention contains fructose, wherein the content of fructose is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup.

[0114] Preferably, the syrup according to the invention contains fructose, wherein the content of fructose is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup.

[0115] Preferably, the syrup according to the invention contains essentially no fructose.

[0116] Preferably, the syrup according to the invention contains glycerol, wherein the content of glycerol is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup.

[0117] Preferably, the syrup according to the invention contains glycerol, wherein the content of glycerol is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup.

[0118] Preferably, the syrup according to the invention contains essentially no glycerol.

[0119] Preferred embodiments A¹ to A¹², B¹ to B¹², C¹ to C¹², D¹ to D¹², E¹ to E¹², F¹ to F¹², G¹ to G¹², H¹ to H¹², I¹ to I¹², and J¹ to J¹² of the syrup according to the invention are compiled in the table here below (all weight percent relative to the overall content of cellobiose (DP2) and the one or more cel- looligosaccharides (DP3-10) that are contained in the syrup in dissolved form; DP2 = cellobiose, DP3 = cellotriose, DP4 = cellotetraose, DP>4 = higher cellooligosaccharides):

[0120] Another aspect of the invention relates to a process for the preparation of a syrup according to the invention as described above, the process comprising the steps of

(a) providing a mixture comprising

- a starting material selected from glucose and cellobiose;

- glucose- 1 -phosphate; and

- a phosphorylase; (b) reacting the starting material with the glucose- 1 -phosphate under catalysis of the phosphorylase thereby obtaining a reaction mixture comprising cellooligosaccharide and phosphate;

(c) optionally purifying the reaction mixture obtained in step (b) thereby obtaining a purified reaction mixture; and

(d) evaporating water from the reaction mixture obtained in step (b) or from the purified reaction mixture obtained in step (c).

[0121] Preferably, the phosphorylase is a cellobiose phosphorylase, a cellotriose phosphorylase, a cel- lotetraose phosphorylase, a cellodextrin phosphorylase, or a mixture thereof.

[0122] Preferably, the phosphorylase is a cellotriose phosphorylase.

[0123] In preferred embodiments of the process according to the invention, step (a) involves providing cellobiose as a starting material at a concentration within the range of from 100 to 300 mM, preferably 125±25 mM or 250±25 mM.

[0124] Preferably, the ratio of phosphorylase to cellobiose is within the range of 1.5 to 5.0 U/mmol, preferably 2.1±0.5 U/mmol or 4.2±0.5 U/mmol.

[0125] In preferred embodiments of the process according to the invention, step (a) involves hydrolysis of sucrose to glucose- 1 -phosphate and fructose in the presence of phosphate under catalysis of a sucrose phosphorylase.

[0126] In preferred embodiments of the process according to the invention, step (a) involves providing sucrose as a starting material at a concentration within the range of from 200 to 800 mM, preferably 250±25 mM, 500±25 mM or 750±25 mM.

[0127] Preferably, the ratio of sucrose phosphorylase to sucrose is within the range of 1.5 to 5.0 U/mmol, preferably 2.1±0.5 U/mmol or 4.2±0.5 U/mmol.

[0128] In preferred embodiments of the process according to the invention, step (c) involves at least one of ultrafdtration, nanofdtration, and electrodialysis.

[0129] Another aspect of the invention relates to a foodstuff, beverage, feed or cosmetic composition comprising a syrup according to the invention as described above.

[0130] Another aspect of the invention relates to the use of a syrup according to the invention as described above as additive for foodstuffs, beverages, feed or cosmetic compositions.

[0131] The following examples further illustrate the invention but are not to be construed as limiting its scope.

[0132] The work was carried out as part of an EU-funded project (Horizon 2020).

Example 1:

[0133] In preliminary experiments, cellobiose and cellooligosaccharides (COS) were synthesized from sucrose and either glucose or cellobiose by P-l,4-linking glucose units. For that purpose, in a one pot synthesis sucrose and phosphate were converted into glucose- 1 -phosphate and fructose as a byproduct under catalysis of a first enzyme, namely a mutant of sucrose phosphorylase from Bifidobacterium ad- olensis (El). The thus obtained glucose- 1-phsophate was subsequently reacted with different starting materials (glucose or cellobiose) under catalysis of different phosphorylases E2, E3 or E4, namely

- E2: a mutant Cu-CBP_mutl of cellobiose phosphorylase from Cellulomonas uda (Cu-CBP), as described and claimed in claim 1 ofWO 2016/038141 Al;

- E3: a mutant Cu-CBP_mut2 of cellobiose phosphorylase from Cellulomonas uda (Cu-CBP), as described in Z. Ubiparip et al., Applied Microbiology and Biotechnology (2020) 104:8327-8337; and

- E4: cellodextrin phosphorylase from Clostridium cellulosi (Cc-CDP).

[0134] The synthetic routes 1 to 3 are compiled in the following table:

DP: degree of polymerization

Example 2:

[0135] Synthetic route 3 was further investigated, in particular the influence of the enzyme : substrate ratio and the concentration on the product distribution, i.e. on the relative content of cellooligosaccha- rides within the product mixture.

[0136] All reactions were performed in potassium phosphate buffer at pH 6.3 and a concentration of 73 mM.

[0137] The concentrations of the first enzyme El and its substrate sucrose as well as the concentration of the second enzyme E4 and its substrate cellobiose are compiled in the table here below:

[0138] The enzymatic conversions were carried out as follows: The substrates were mixed in ratios and concentration of the above table. The thus obtained mixtures were heated to constant reaction conditions of 45°C. The enzymes El and E4 were added. Sampling times were after Oh, 2h, 4h, 6h, 8h, 24h, 26h, and 28h. For sampling, 2ml of the reaction mixture were taken and heat inactivated for 5 min at 99°C at 900 rpm in a thermo block and subsequently centrifugated for 5 min at 10 000 g. The whole supernatant was taken and transferred to a new reaction vessel, stored at 4°C till all samples were taken and analyzed by HPAEC-PAD, i.e. high performance anion exchange chromatography (HPAEC) with pulsed amperometric detection (PAD).

[0139] The results are shown in Figures 1 to 4. Increase and decrease of g/L over a time of 28 h for sucrose, glucose, glucose- 1 -phosphate (G1P), fructose, cellobiose and cellooligosaccharides CD3-CD7 were monitored and g/L CD3-CD7 yield at 24 h are shown. Figure 1 relates to Example 2-1: 171 g/L sucrose, 85.5 g/L cellobiose, 2.1 U E1 / 2.1 U E4/ mmol substrate. Figure 2 relates to Example 2-2: 171 g/L sucrose, 85.5 g/L cellobiose, 4.2 U El / 2.1 U E4/ mmol substrate. Figure 3 relates to Example 2-3: C 256.5 g/L sucrose, 85.5 g/L cellobiose, 2.1 U El / 2.1 U E4/ mmol substrate. Figure 4 relates to Example 2-4: 85.5 g/L sucrose, 42.75 g/L cellobiose, 4.2 U El / 4.2 U E4/ mmol substrate.

[0140] As demonstrated by the experimental data, Examples 2-1 to 2-3 were basically similar. Using more El per mmol sucrose (Example 2-2) or more sucrose (Example 2-3) compared to Example 2-1 did not yield in a significantly higher sucrose breakdown or formation of G1P, respectively. After 28 h reactions were not completed, because substantial amounts of residual sucrose and unreacted G1P were still present. Longer chain cellodextrins were formed until the experiment was stopped. If the cellodex- trin formation was too fast, longer chain cellodextrins would be still present in the E4 binding site and another glucose unit would be added thereby resulting in long-chain cellodextrins, which would precipitate (compare Example 2-1 and Example 2-4; Example 2-4 contains more units / substrate resulting in faster reaction). Cellodextrin yields differed at the end of Examples 2-1 to 2-3, which resulted from the fact that the interactions were somewhat different within the respective reactions.

[0141] No significant long chain cellodextrins precipitated from these reaction mixtures as seen in Figure 5, which shows the % distribution of cellobiose and CD3-CD7 in Examples 2-1 to 2-4 (different concentrations of sucrose / cellobiose / El / E4). Figure 6 shows the pellet formation after centrifugation as marker for cellodextrin precipitation at t = 24h.

[0142] The percentage distribution of cellobiose and the various cellodextrins (CD3-CD7) was different between Examples 2-1 to 2-3 (Figures 1-3). Example 2-3 with the highest input of sucrose built highest amounts of cellotriose (CD3) and smallest amounts of longer-chain cellodextrins. On the other hand, Example 2-1 built smaller amounts of cellotriose (CD3) and higher amounts of longer-chain cellodextrins compared to Example 2-2 and Example 2-3, which also could be explained with the behavior of the E4 binding site as described above. The goal of reducing the cellobiose concentration was achieved in all reactions. In Example 2-4 after 24 h all sucrose was used (Figure 4). The cellodextrin distribution was higher towards longer-chain cellodextrins, whereby the reaction became cloudy due to insoluble cellodextrins and these formed a pellet after centrifugation (Figure 6).

[0143] The best result within these experiments was achieved with 171 g/L sucrose, 85.5 g/L cellobiose, 2.1 U El and E4 / mmol substrate of Example 2-1. 138 g/L of cellobiose and CD3-CD7 and 116 g/L of CD3-CD7 could be formed.

Example 3: [0144] For scale-up of synthetic route 3 using second enzyme E4 and also to avoid precipitation in the ultra-fdtration unit, the reaction conditions of Example 2-1 were chosen. It can be assumed that higher yields could be achieved and cellodextrin composition could vary if another substrate composition and/or enzyme ratio is used.

[0145] The following reaction mixture was prepared:

[0146] Reaction and subsequent fdtration were carried out under the following conditions: 1. Reaction conditions: 48°C/ 18Hz (528 rpm); 2. Reaction time: 24h; 3. Ultrafiltration; 10 kDa; 4. Nanofiltration.

[0147] The results of HPLC measurements FOR production route 3 are compiled in the table here below:

*No electrodialysis of retentate took place

[0148] At the end approx. 250L retentate with a purity of 58% could be obtained after nanofiltration which means approx. 36 kg CD3-CD8 were produced. Using an additional filtration step (ultra-filtration) the purity could be further increased to 78%. Thus, a purity of >80% can be easily achieved with some adjustments on the filtration parameters and/or with the use of an invertase which hydrolyses sucrose. By just applying the invertase the purity would raise to 87%. [0149] The solutions obtained by the above enzymatic syntheses were evaporated. Surprisingly, there was no spontaneous formation of crystals so that the syrup obtained could be concentrated to 84 wt.-% dry substance without precipitation.

[0150] This syrup contained glucose, fructose, glycerol, sucrose, cellobiose, cellotetraose and cellotri- ose. It was hypothesized that glycerol and the monosaccharides prevent crystallization. They were therefore separated off by nanofiltration and the process solution obtained was again concentrated. It was surprisingly found that even in absence of glycerol no precipitation occurs.

Example 4:

[0151] For scale-up of synthetic route 2 using second enzyme E3 and purification and also to avoid precipitation in the ultra-filtration unit, the following reaction conditions were chosen: 1. Reaction mixture: 145 mM sucrose, 145 mM cellobiose, potassium phosphate buffer, pH 6.3, enzyme El 0.61 U/mL, enzyme E3 0.31 U/mL; 2. Reaction conditions: 48°C/ 18Hz (528 rpm); 3. Reaction time: 24h; 4. Ultrafiltration 10 kDa; 5. Electrodialysis of filtrate (20% on dilute and concentrate site, 200 V); 6. Rotary evaporation of dilute.

[0152] The cellodextrin production was scaled up to 173 L batch scale. The following table presents the composition of the substrate stream, the intermediate product stream and the final product solution:

* total syrup weight: 125 kg; 10-20 % dry substance (DS)

Example 5:

[0153] Besides the fractionation of the respective component, a typical cooling crystallization of cellobiose was tested. Since the solubility of the cellodextrins (CD3-8) is lower than the solubility of cellobiose, it was promising to easily achieve certain amounts of crystalline cellodextrins applying cellobiose crystallization procedure.

[0154] The solution to be crystallized was concentrated in a rotary vacuum evaporator until a turbidity could be detected with the naked eye. After first spontaneous crystallization, the solution was transferred into a mixed vessel and was cooled down (cooling crystallization, Table 2). After reaching the target temperature, the massecuite was centrifugated. The crystallization conditions are compiled in the table here below:

[0155] The first crystallization batch was done with a cellodextrin solution produced by E3 (synthetic route 2). Contrary to expectation, this solution was not crystallizable. The evaporation led to a dry substance higher than 83% DS which is much higher than expected. A second batch provided the same result.

[0156] Residual glycerol left from the synthesis was identified as a potential crystallization inhibitor. Due to high enzyme-use the glycerin content was significant (> 13%) and therefore a possible reason for non-crystallization. To remove the glycerol, a nano-filtration step using a membrane having a suitable cut off was considered.

[0157] For removal, a crossflow filtration unit was used. The parameters are compiled in the table here below:

[0158] Solution was pumped from the feed vessel to the plant by high pressure pump. There, it was recirculated by cross flow pump over tube heat exchanger and two membrane housings arranged in parallel. The cross flow avoids sediments on the membrane surface which harm filtration. The retentate flow was transferred back to feed vessel. It contained everything that did not pass the membrane. The permeate passed the membrane. It contained everything that had a smaller size than the membrane pores. [0159] To ensure the filtration was not harmed by any effect from concentration, the filtration unit was processed in diafiltration mode. So, the volume of permeate was directly replaced by pure water to the feed vessel. All trials made were processed until a constant brix equals zero could be measured in permeate flow.

[0160] Figure 7 shows the composition of the synthesis solution and the filtrated synthesis solution with second enzyme E3 (synthetic route 2) after treatment with the membrane - filtrated solution measured with 16 and 70 Bx. Figure 7 confirms a significant reduction of glycerin, glucose and fructose content in the filtrated synthesis solution. The nano filtration was able to remove >90% of glycerin, >98% of glucose and >99% of fructose.

[0161] The results are compiled in the table here below:

DP: degree of polymerization; DF: dilution factor; M: measurement; Bx: Brix; sys.: synthesis solution; tsys.: treated synthesis solution; ret.: retentate

[0162] The nano-fdtrated process solution was evaporated as described above. However, the fdtrated synthesis solution was not crystallizable either. Evaporated process solution synthesized with E3 did not crystalize either.

[0163] Furthermore, seed crystals (powdered cellobiose) were used to induce crystallization. However, these seed crystals remained in the syrup, as shown in Figure 8. Figure 8 shows in the tube on the right the cellodextrin syrup (E3) and in the tube on the left the cellodextrin syrup containing seed crystals (cellobiose).

Example 6:

[0164] An “one pot” reaction mix, with sucrose, cellobiose, potassium phosphate, CuCBP OCP (E3) and SP Bado (El) was investigated in an approx. 200 L reaction. Method: 172L reaction mix for DP3 production:

[0165] Reaction conditions: temperature: 45°C/ 18Hz (528rpm); reaction time: 22.5h; ultrafiltration of reaction: crossflow 4 m³/h; electrodialysis of filtrate: 200V till > 0.05 ms/cm; nanofiltration of reaction: crossflow 5m³/h; DP3 production in a “one pot” reaction; sampling times: 0, 22.5h of reaction, end of ultrafiltration, diluate of electrodialysis, end of nanofiltration (retentate and permeate).

[0166] Sampling: 12 ml of the reaction mixture were taken and heat inactivated 5 min/ 99°C/ 900rpm in a thermoblock (samples after the ultrafiltration step did not have to be heat inactivated), 0.45pm filtrated, stored at 4°C till all samples are taken. Then 6 ml were subjected to G1P analysis and 6 ml were used for density/ pH determination and for carbon analysis. Carbon analysis was performed by HPLC measurement (NH2-RP column, RID detector, Eluent: 67.5% acetonitrile 32.5% H2O dest., flow rate: 1.5ml/ min, column temperature: 40°C). Rotary evaporation of retentate (nanofiltration) to approximately 80Brix (80% dry substance). 0167] The overall results of HPLC and HPIC measurements during DP3 production are compiled in the table here below:

0168] At the end of reaction the whole sucrose was implemented, only a minor amount of G1P (0.93g/L) was accumulated and 21 g/L CD3-4 were produced. The oncentrations of the components were minor affected by the ultrafiltration. After electrodialysis all G1P and phosphates were removed. After rotary evaporation syrup of 82 Brix was obtained. 0169] Results of electrodialysis are compiled in the table here below:

Claims

Patent claims:

1. A syrup comprising one or more cellooligosaccharides in dissolved form at an overall content of at least 12.5 wt.-%, preferably at least 50 wt.-%, relative to the total weight of the syrup.

2. The syrup according to claim 1, which comprises essentially no undissolved cellooligosaccharides, preferably no undissolved material at all.

3. The syrup according to claim 1 or 2, which is oversaturated with respect to the one or more cellooligosaccharides in dissolved form.

4. The syrup according to any of the preceding claims, wherein the overall content of the one or more cellooligosaccharides is at least 15 wt.-%, preferably at least 20 wt.-%, more preferably at least 25 wt.-%, still more preferably at least 30 wt.-%, yet more preferably at least 35 wt.-%, even more preferably at least 40 wt.-%, most preferably at least 45 wt.-%, and in particular at least 50 wt.-%, in each case relative to the total weight of the syrup.

5. The syrup according to any of the preceding claims, wherein the overall content of the one or more cellooligosaccharides is at least 52 wt.-%, preferably at least 54 wt.-%, more preferably at least 56 wt.-%, still more preferably at least 58 wt.-%, yet more preferably at least 60 wt.-%, even more preferably at least 62 wt.-%, most preferably at least 64 wt.-%, and in particular at least 66 wt.-%, in each case relative to the total weight of the syrup.

6. The syrup according to any of the preceding claims, wherein the overall content of the one or more cellooligosaccharides is at least 68 wt.-%, still more preferably at least 70 wt.-%, yet more preferably at least 72 wt.-%, even more preferably at least 74 wt.-%, most preferably at least 76 wt.-%, and in particular at least 78 wt.-%, in each case relative to the total weight of the syrup.

7. The syrup according to any of the preceding claims, which has a dry solids content of at least 15 wt.-%, preferably at least 20 wt.-%, more preferably at least 25 wt.-%, still more preferably at least 30 wt.-%, yet more preferably at least 35 wt.-%, even more preferably at least 40 wt.-%, most preferably at least 45 wt.-%, and in particular at least 50 wt.-%, in each case relative to the total weight of the syrup.

8. The syrup according to any of the preceding claims, wherein the dry solids content is at least 55 wt.-%, preferably at least 60 wt.-%, more preferably at least 65 wt.-%, still more preferably at least 70 wt.-%, yet more preferably at least 75 wt.-%, even more preferably at least 80 wt.-%, most preferably at least 82.5 wt.-%, and in particular at least 85 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which has a water content of at least 5.0 wt.- %, or at least 10 wt.-%, or at least 15 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which has a water content of at most 70 wt.- %, preferably at most 65 wt.-%, more preferably at most 60 wt.-%, still more preferably at most 55 wt.-%, yet more preferably at most 50 wt.-%, even more preferably at most 45 wt.-%, most preferably at most 40 wt.-%, and in particular at most 35 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which has a water content of at most 30 wt.- %, preferably at most 28 wt.-%, more preferably at most 26 wt.-%, still more preferably at most 24 wt.-%, yet more preferably at most 22 wt.-%, even more preferably at most 20 wt.-%, most preferably at most 18 wt.-%, and in particular at most 16 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, wherein the overall content of the one or more cellooligosaccharides amounts to at least 55 wt.-%, preferably at least 60 wt.-%, more preferably at least 65 wt.-%, still more preferably at least 70 wt.-%, yet more preferably at least 75 wt.-%, even more preferably at least 80 wt.-%, most preferably at least 85 wt.-%, and in particular at least 90 wt.-%, in each case relative to the dry solids content of the syrup. The syrup according to any of the preceding claims, wherein the overall content of the one or more cellooligosaccharides amounts to at least 92 wt.-%, preferably at least 93 wt.-%, more preferably at least 94 wt.-%, still more preferably at least 95 wt.-%, yet more preferably at least 96 wt.-%, even more preferably at least 97 wt.-%, most preferably at least 98 wt.-%, and in particular at least 99 wt.-%, in each case relative to the dry solids content of the syrup. The syrup according to any of the preceding claims, wherein the sum of the content of water and the overall content of the one or more cellooligosaccharides amounts to at least 55 wt.-%, preferably at least 60 wt.-%, more preferably at least 65 wt.-%, still more preferably at least 70 wt.-%, yet more preferably at least 75 wt.-%, even more preferably at least 80 wt.-%, most preferably at least 85 wt.-%, and in particular at least 90 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, wherein the sum of the content of water and the overall content of the one or more cellooligosaccharides amounts to at least 92 wt.-%, preferably at least 93 wt.-%, more preferably at least 94 wt.-%, still more preferably at least 95 wt.-%, yet more preferably at least 96 wt.-%, even more preferably at least 97 wt.-%, most preferably at least 98 wt.-%, and in particular at least 99 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, wherein the sum of the content of cellobiose and the overall content of the one or more cellooligosaccharides amounts to at least 55 wt.-%, preferably at least 60 wt.-%, more preferably at least 65 wt.-%, still more preferably at least 70 wt.-%, yet more preferably at least 75 wt.-%, even more preferably at least 80 wt.-%, most preferably at least 85 wt.-%, and in particular at least 90 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, wherein the sum of the content of water and the overall content of the one or more cellooligosaccharides amounts to at least 92 wt.-%, preferably at least 93 wt.-%, more preferably at least 94 wt.-%, still more preferably at least 95 wt.-%, yet more preferably at least 96 wt.-%, even more preferably at least 97 wt.-%, most preferably at least 98 wt.-%, and in particular at least 99 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains cellobiose and cellotriose; preferably wherein the cellooligosaccharides that are contained in the syrup in dissolved form are predominantly cellobiose and/or cellotriose, i.e. wherein among all cellooligosaccharides that are contained in the syrup in dissolved form, cellobiose and/or cellotriose are the individual cellooligosaccharides having the highest content compared to each of the other cellooligosaccharides that are contained in the syrup in dissolved form. The syrup according to claim 18, wherein the content of cellobiose is greater than the content of cellotriose. The syrup according to claim 18, wherein the content of cellotriose is greater than the content of cellobiose. The syrup according to any of the preceding claims, which contains cellotriose and cellotetraose; preferably wherein the cellooligosaccharides that are contained in the syrup in dissolved form are predominantly cellotriose and/or cellotetraose, i.e. wherein among all cellooligosaccharides that are contained in the syrup in dissolved form, cellotriose and/or cellotetrraose are the individual cellooligosaccharides having the highest content compared to each of the other cellooligosaccha- rides that are contained in the syrup in dissolved form. The syrup according to claim 21, wherein the content of cellotriose is greater than the content of cellotetraose. The syrup according to claim 21, wherein the content of cellotetraose is greater than the content of cellotriose. The syrup according to any of the preceding claims, which contains cellobiose and cellotetraose. The syrup according to claim 24, wherein the content of cellobiose is greater than the content of cellotetraose. The syrup according to claim 24, wherein the content of cellotetraose is greater than the content of cellobiose. The syrup according to any of the preceding claims, which contains cellotriose, wherein the content of cellotriose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.- %, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 35 wt.-%, and in particular at least 40 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains cellotriose, wherein the content of cellotriose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.- %, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains cellotriose, wherein the content of cellotriose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.- %, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 35 wt.-%, and in particular at least 40 wt.-%, in each case relative to the dry solids content of the syrup. The syrup according to any of the preceding claims, which contains cellotriose, wherein the content of cellotriose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.- %, in each case relative to the dry solids content of the syrup. The syrup according to any of the preceding claims, which contains cellotetraose, wherein the content of cellotetraose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.-%, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 35 wt.-%, and in particular at least 40 wt.- %, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains cellotetraose, wherein the content of cellotetraose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains cellotetraose, wherein the content of cellotetraose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.-%, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 35 wt.-%, and in particular at least 40 wt.- %, in each case relative to the dry solids content of the syrup. The syrup according to any of the preceding claims, which contains cellotetraose, wherein the content of cellotetraose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.-%, in each case relative to the dry solids content of the syrup. The syrup according to any of the preceding claims, which contains cellotriose and cellotetraose, wherein the sum of the content of cellotriose and the content of cellotetraose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.-%, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 35 wt.-%, and in particular at least 40 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains cellotriose and cellotetraose, wherein the sum of the content of cellotriose and the content of cellotetraose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains cellotriose and cellotetraose, wherein the sum of the content of cellotriose and the content of cellotetraose is at least 5 wt.-%, preferably at least 10 wt.-%, more preferably at least 15 wt.-%, still more preferably at least 20 wt.-%, yet more preferably at least 25 wt.-%, even more preferably at least 30 wt.-%, most preferably at least 35 wt.-%, and in particular at least 40 wt.-%, in each case relative to the dry solids content of the syrup. The syrup according to any of the preceding claims, which contains cellotriose and cellotetraose, wherein the sum of the content of cellotriose and the content of cellotetraose is at most 85 wt.-%, preferably at most 80 wt.-%, more preferably at most 75 wt.-%, still more preferably at most 70 wt.-%, yet more preferably at most 65 wt.-%, even more preferably at most 60 wt.-%, most preferably at most 55 wt.-%, and in particular at most 50 wt.-%, in each case relative to the dry solids content of the syrup. The syrup according to any of the preceding claims, which contains cellopentaose, wherein the content of cellopentaose is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains cellopentaose, wherein the content of cellopentaose is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains essentially no cellopentaose. The syrup according to any of the preceding claims, which contains cellohexaose, wherein the content of cellohexaose is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least

1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains cellohexaose, wherein the content of cellohexaose is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains essentially no cellohexaose. The syrup according to any of the preceding claims, which contains essentially no celloheptaose, essentially no cellooctaose, essentially no cellononaose, and essentially no cellodecaose. The syrup according to any of the preceding claims, which contains cellobiose, wherein the content of cellobiose is at least 2.5 wt.-%, preferably at least 5.0 wt.-%, more preferably at least 7.5 wt.-%, still more preferably at least 10 wt.-%, yet more preferably at least 12.5 wt.-%, even more preferably at least 15 wt.-%, most preferably at least 17.5 wt.-%, and in particular at least 20 wt.- %, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains cellobiose, wherein the content of cellobiose is at most 40 wt.-%, preferably at most 35 wt.-%, more preferably at most 30 wt.-%, still more preferably at most 25 wt.-%, yet more preferably at most 20 wt.-%, even more preferably at most 15 wt.-%, most preferably at most 10 wt.-%, and in particular at most 5.0 wt.- %, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains essentially no cellobiose. The syrup according to any of the preceding claims, which contains sucrose, wherein the content of sucrose is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains sucrose, wherein the content of sucrose is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains essentially no sucrose. The syrup according to any of the preceding claims, which contains glucose, wherein the content of glucose is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains glucose, wherein the content of glucose is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains essentially no glucose. The syrup according to any of the preceding claims, which contains glucose- 1 -phosphate, wherein the content of glucose- 1 -phosphate is at least 0. 1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains glucose- 1 -phosphate, wherein the content of glucose- 1 -phosphate is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains essentially no glucose- 1- phosphate. The syrup according to any of the preceding claims, which contains fructose, wherein the content of fructose is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains fructose, wherein the content of fructose is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.-%, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains essentially no fructose. The syrup according to any of the preceding claims, which contains glycerol, wherein the content of glycerol is at least 0.1 wt.-%, preferably at least 0.5 wt.-%, more preferably at least 1.0 wt.-%, still more preferably at least 1.5 wt.-%, yet more preferably at least 2.0 wt.-%, even more preferably at least 2.5 wt.-%, most preferably at least 3.0 wt.-%, and in particular at least 3.5 wt.-%, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains glycerol, wherein the content of glycerol is at most 5.0 wt.-%, preferably at most 4.5 wt.-%, more preferably at most 4.0 wt.- %, still more preferably at most 3.5 wt.-%, yet more preferably at most 3.0 wt.-%, even more preferably at most 2.5 wt.-%, most preferably at most 2.0 wt.-%, and in particular at most 1.5 wt.- %, in each case relative to the total weight of the syrup. The syrup according to any of the preceding claims, which contains essentially no glycerol. A process for the preparation of a syrup according to any of the preceding claims, the process comprising the steps of

(a) providing a mixture comprising

- a starting material selected from glucose and cellobiose;

- glucose- 1 -phosphate; and

- a phosphorylase;

(b) reacting the starting material with the glucose- 1 -phosphate under catalysis of the phosphorylase thereby obtaining a reaction mixture comprising cellooligosaccharide and phosphate;

(c) optionally purifying the reaction mixture obtained in step (b) thereby obtaining a purified reaction mixture; and (d) evaporating water from the reaction mixture obtained in step (b) or from the purified reaction mixture obtained in step (c). The process according to claim 64, wherein the phosphorylase is a cellobiose phosphorylase, a cellotriose phosphorylase, a cellotetraose phosphorylase, a cellodextrin phosphorylase, or a mixture thereof. The process according to claim 64 or 65, wherein the phosphorylase is a cellotriose phosphorylase. The process according to any of claims 64 to 66, wherein step (a) involves hydrolysis of sucrose to glucose- 1 -phosphate and fructose in the presence of phosphate under catalysis of a sucrose phosphorylase. The process according to any of claims 64 to 67, wherein step (c) involves at least one of ultrafiltration, nanofiltration, and electrodialysis. A foodstuff, beverage, feed or cosmetic composition comprising a syrup according to any of claims 1 to 63. Use of a syrup according to any of claims 1 to 63 as additive for foodstuffs, beverages, feed or cosmetic compositions.