CN108300748B - Method for preparing alternan oligosaccharide by holoenzyme method - Google Patents
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- CN108300748B CN108300748B CN201810148066.3A CN201810148066A CN108300748B CN 108300748 B CN108300748 B CN 108300748B CN 201810148066 A CN201810148066 A CN 201810148066A CN 108300748 B CN108300748 B CN 108300748B
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- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
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- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
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- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/22—Preparation of compounds containing saccharide radicals produced by the action of a beta-amylase, e.g. maltose
Abstract
The invention discloses a method for preparing alternan oligosaccharide by a holoenzyme method, belonging to the technical field of food biology. According to the invention, potato starch and sucrose are used as raw materials, the proportion of the potato starch and the sucrose is adjusted, and the high-temperature acidic alpha-amylase, beta-amylase, pullulanase, maltogenic amylase and alternan sucrase are added for catalytic reaction for 72 hours, so that the final substrate glycoside conversion efficiency reaches 88.9%, and a foundation is laid for the industrial preparation of alternan oligosaccharide.
Description
Technical Field
The invention relates to a method for preparing alternan oligosaccharide by a holoenzyme method, in particular to a method for preparing alternan oligosaccharide with the polymerization degree of 3-8 by using potato starch and cane sugar as raw materials and adopting the holoenzyme method, belonging to the technical field of food biology.
Background
Alternan oligosaccharides are composed of glucose units. The main chain is formed by connecting glucose units through alpha-glucopyranose 1, 3-glycosidic bonds and alpha-1, 6-glucopyranose glycosidic bonds alternately.
Alternan oligosaccharides have a wide range of uses in various fields.
In the food industry, alternan oligosaccharides can be used to prepare low-glycemic syrups. Such syrups have a relatively low glycemic index, while further increasing product clarity, and play an important role in food formulation.
In the pharmaceutical industry, as carriers and stabilizers, as excipients for active ingredients in pharmaceuticals.
Alternan oligosaccharides are extremely potent as prebiotics for the control of intestinal bacterial pathogens in clinical applications. By treating the animal with an amount of one or more alternan oligosaccharides effective to promote the growth of beneficial bacteria, the population of enteropathogenic bacteria, particularly Salmonella species, enteropathogenic Escherichia coli, and Clostridium perfringens, can be substantially reduced or inhibited.
At present, alternan sucrase is utilized at home and abroad to catalyze the reaction of sucrose and acceptor oligosaccharide to produce alternan oligosaccharide, wherein maltose is used as a good acceptor, and alternan oligosaccharide with the polymerization degree of 3-8 can be produced. The degree of polymerization of alternan oligosaccharides can vary with the concentration and relative ratio of sucrose to acceptor maltose. The reaction product is usually composed of a mixture of oligosaccharides with different degrees of polymerization. At relatively high sucrose and maltose ratios, more glycosyl units are transferred into the glucan and a product with a higher degree of polymerisation is obtained. In contrast, at low sucrose to maltose ratios, the major reaction product is the product resulting from the transfer of a single glycosyl unit to the acceptor.
Domestic research and reports on the preparation of alternan oligosaccharides are few, and only partial research on oligomeric tetrasaccharides in the preparation of alternan oligosaccharides is involved, while foreign research on alternan oligosaccharides only remains in the field of component identification of products with maltose as a receptor, and the production of alternan oligosaccharides is not studied in detail. In the process of industrial production, if only sucrose and maltose are used as raw materials to prepare alternan oligosaccharide, huge cost pressure is brought to the industrial preparation of alternan oligosaccharide due to the high raw material cost of maltose.
Disclosure of Invention
The invention aims to provide a method for preparing alternan oligosaccharide, which takes low-cost potato starch and cane sugar as raw materials and prepares alternan oligosaccharide by a holoenzyme method, thereby laying a foundation for industrial production of alternan oligosaccharide.
The method sequentially comprises the steps of raw material pretreatment, gelatinization, liquefaction, saccharification, alternan oligosaccharide generation and the like.
In one embodiment of the present invention, the pretreatment is to suspend 5-30% (g/100mL) of potato starch in 20-200 mM phosphate buffer (pH 3-7).
In one embodiment of the present invention, the gelatinization is to gelatinize starch by continuously stirring in a boiling water bath for 1 to 10 min.
In one embodiment of the present invention, the gelatinization is performed by suspending 5 to 10% (m/v) potato starch in 50mM phosphate buffer (pH 4.5) and stirring in a boiling water bath.
In one embodiment of the present invention, the liquefaction is performed by adding 5 to 100U/g of high temperature acidic alpha-amylase, continuously stirring in a boiling water bath for 1 to 10min, and then adding 0 to 10M hydrochloric acid to adjust the pH to 2.0 to 6.0 or less, thereby terminating the liquefaction.
In one embodiment of the invention, the liquefaction is to add 5-10U/g high-temperature acidic alpha-amylase to the gelatinized product, continuously stir the gelatinized product in a boiling water bath for 4-10 min, and then add 1-10M hydrochloric acid to adjust the pH to 2.0-4.0 so as to stop liquefaction.
In one embodiment of the invention, the saccharification is carried out by adding 5-100U/g beta-amylase and 1-100U/g pullulanase, and reacting in a water bath shaker at 30-80 ℃ for 5-240 h; then adding 5-100U/g maltogenic amylase, and reacting at 30-80 ℃ for 5-100 h.
In one embodiment of the invention, the saccharification comprises: primary saccharification: cooling the starch liquefaction liquid to room temperature, adjusting the pH value to 5.2, adding 5-15U/g beta-amylase and 1-5U/g pullulanase, and reacting for 24 hours in a water bath shaking table at 60 ℃; and (3) secondary saccharification: adjusting the pH of the reaction solution to 5.5, adding 5-10U/g maltogenic amylase, and reacting at 60 deg.C for 10 hr.
In one embodiment of the invention, the alternan oligosaccharide is produced by carrying out secondary saccharification, then inactivating enzyme, sequentially adding 1-30% of sucrose and 0.1-100U/g of alternan sucrase, and reacting in a water bath shaker at 30-80 ℃ for 5-240 h.
In one embodiment of the present invention, the alternan oligosaccharide is produced by carrying out secondary saccharification, then inactivating the enzyme, and adding 20 to 30% of sucrose and 0.1 to 5U/g of alternan sucrase in sequence to react at 40 ℃ for 34 hours.
In one embodiment of the invention, the maltogenic amylase is of Bacillus stearothermophilus origin.
In one embodiment of the invention, the alternan sucrase is of Leuconostoc citreum origin.
Has the advantages that: the invention provides an alteman oligosaccharide prepared by a holoenzyme method, which takes potato starch and cane sugar as raw materials, adjusts the proportion of the potato starch and the cane sugar, and finally achieves a substrate glycoside conversion efficiency of 88.9 percent when high-temperature acid alpha-amylase, beta-amylase, pullulanase, maltogenic amylase and alteman sucrase are added for catalytic reaction for 72 hours in sequence, thereby laying a foundation for the industrial preparation of the alteman oligosaccharide.
Drawings
Figure 1 HPLC profile of the product. The solvent peak, monosaccharide, disaccharide, trisaccharide, tetrasaccharide, pentasaccharide, hexasaccharide and heptasaccharide are shown from left to right in sequence. (the product is a mixture of oligosaccharides with different degrees of polymerization)
Figure 2 HPLC profile of the product. The solvent peak, monosaccharide, disaccharide, trisaccharide, tetrasaccharide, pentasaccharide and hexasaccharide are shown from left to right in sequence. (the product is a mixture of oligosaccharides with different degrees of polymerization)
FIG. 3 HPLC chromatogram of the product. The solvent peak, monosaccharide, disaccharide, trisaccharide, tetrasaccharide and pentasaccharide (the product is a mixture of oligosaccharides with different polymerization degrees) are sequentially arranged from left to right
Detailed Description
The method for measuring the activity of the maltogenic amylase comprises the following steps: soluble starch was weighed out to a final concentration of 1% (m/v), dissolved in 50mM phosphate buffer pH5.5 and pre-heated in a water bath at 60 ℃ for 10 min. Adding 100ul enzyme solution, reacting for 30min, adding 3ml of LDNS, boiling for 7min, cooling rapidly, adding distilled water to 15ml, and measuring absorbance at 540 nm.
Maltogenic amylase enzyme activity definition: the amount of enzyme required to hydrolyze soluble starch to 1. mu. mol of glucose per minute was defined as the enzyme activity (U) of one unit of maltogenic amylase.
The method for measuring the enzyme activity of the alternan sucrase comprises the following steps: keeping the temperature of the enzyme solution to be detected at 45 ℃ for 30min, adding 0.4mL of the enzyme solution to 3.6mL of sucrose NaAc-HAc buffer solution (50mmol/L, pH5.4) to ensure that the final concentration of sucrose is 10%, preheating at 40 ℃ for 10min, adding 100ul of the enzyme solution, reacting for 30min, adding 3mLDNS, boiling for 7min, rapidly cooling, adding distilled water to fix the volume to 15mL, and measuring the absorbance at 540 nm.
Alternan sucrase enzyme activity definition: the amount of enzyme required to hydrolyze sucrose to 1. mu. mol fructose per minute was defined as the enzyme activity (U) of one unit of sucrose phosphorylase.
HPLC detection of the product: the amounts of sucrose, glucose, fructose, and monosaccharides in the final reaction system were determined by HPLC. The chromatographic conditions are as follows: agilent 1200HPLC chromatograph, Agilent autosampler, chromatographic column NH2504E (4.6mm × 250mm), the difference detector is Agilent G1362A; mobile phase adoptionA mixed solution of 75% (v/v) acetonitrile and water was supplied at a flow rate of 0.8mL/min, and the column temperature was set at 35 ℃. The concentration of the corresponding alternan oligosaccharide was determined from the retention time and peak area using an external standard method.
The calculation formula of the transglycosylation efficiency D of alternan oligosaccharide is as follows:
D(％)＝M1/M2*100％
wherein D: molar transglycosidic efficiency (%) for the conversion of sucrose to alternan oligosaccharides;
M1: the number of moles (mol) of fructose produced in the enzymatic conversion reaction;
M2: the number of moles (mol) of sucrose charged into the reaction solution.
EXAMPLE 1 preparation of alternan oligosaccharides by holoenzyme method under optimal reaction conditions
10mL of the enzyme conversion system was carried out in a 50mL closed vessel. Preparing alternan oligosaccharide by utilizing high-temperature acid alpha-amylase, beta-amylase, pullulanase, maltogenic amylase and alternan sucrase in sequence, and comprising the following steps:
pasting: 10% (m/v) potato starch was suspended in 50mM phosphate buffer (pH 4.5) and gelatinized by continuous stirring in a boiling water bath for 1.5 min.
Liquefaction: 10U/g high temperature acid alpha-amylase was added, and after stirring continuously for 4min in a boiling water bath, 1M hydrochloric acid was added to adjust the pH to below 4.0 to stop liquefaction.
Primary saccharification: cooling the starch liquefied liquid to room temperature, adjusting the pH value to 5.2, adding 15U/g beta-amylase and 1U/g pullulanase, and reacting for 24 hours (rotating speed 150rpm) in a water bath shaker at 60 ℃.
And (3) secondary saccharification: the pH of the reaction solution was adjusted to 5.5, and 9.3U/g maltogenic amylase was added thereto, and the mixture was reacted in a shaker at 60 ℃ in a water bath for 10 hours (rotation speed 150 rpm).
After the secondary saccharification, heating in boiling water bath for 5min to inactivate enzyme, adding 20% sucrose and 5U/g alternan sucrase in sequence, and reacting in a water bath shaker at 40 ℃ for 34h (rotating speed 150 rpm). The reaction was then quenched by heating in a boiling water bath for 5min, the reaction was centrifuged and the product was analyzed by HPLC. When the reaction is finished, the glycoside conversion efficiency can reach 88.9 percent, the product is a mixture of oligosaccharides with different polymerization degrees, and chromatographic peaks are shown in figure 1: the solvent peak, monosaccharide, disaccharide, trisaccharide, tetrasaccharide, pentasaccharide, hexasaccharide and heptasaccharide are shown from left to right in sequence.
Comparative example 1 Effect of sucrose and acceptor ratio on reaction products and transglycosidation efficiency
The degree of polymerization of alternan oligosaccharides can vary with the concentration and relative ratio of sucrose to acceptor maltose. The reaction product is usually composed of a mixture of oligosaccharides with different degrees of polymerization. At relatively high sucrose and maltose ratios, more glycosyl units are transferred into the glucan and a product with a higher degree of polymerisation is obtained. In contrast, at low sucrose to maltose ratios, the major reaction product is the product resulting from the transfer of a single glycosyl unit to the acceptor. Thus, by varying the sucrose and acceptor ratio, the transglycosylation efficiency of the product alternan oligosaccharide and the product composition of the product alternan oligosaccharide can be optimized.
The reaction conditions of enzyme addition amount, reaction temperature, reaction time, reaction pH and the like of the enzyme-catalyzed reaction are ensured to be consistent with those of the example 1, the proportions of the raw materials of the potato starch and the cane sugar are respectively adjusted to be 1:1, 1:2 and 2:1, and the enzyme-catalyzed reaction is carried out. After the reaction was complete, the product was analyzed by HPLC. Measured transglycosidation efficiencies were 71.5%, 88.9%, and 55.0%, respectively, and the reaction products were disaccharide-hexasaccharide, disaccharide-heptasaccharide, and disaccharide-pentasaccharide, respectively, with chromatographic peaks shown in FIG. 2, FIG. 1, and FIG. 3.
Comparative example 2 influence of reaction temperature on reaction product and transglycosidation efficiency
In the reaction process of synthesizing alternan oligosaccharide under the catalysis of alternan sucrase, the temperature of a reaction system can influence the activity of alternan sucrase, and further influence the yield of the alternan oligosaccharide as a reaction product. Meanwhile, according to literature reports, it is known that when sucrose and another monosaccharide or disaccharide which can be linked to the enzyme are present in a reaction substrate, the enzyme catalyzes the two saccharides to produce a small molecule oligosaccharide. Since the acceptor molecule is different from the sucrose molecule, the acceptor molecule attacks the glucosyl group or the glucan group and terminates the formation of the glucan chain. While oligosaccharides with a higher degree of polymerization are more difficult to form due to the presence of steric hindrance effects. Therefore, if the temperature of the reaction system affects the activity of alternan, it further affects the formation of oligosaccharides with a higher degree of polymerization, so that the reaction product contains fewer alternan oligosaccharides with a higher degree of polymerization, or even almost no alternan oligosaccharides with a higher degree of polymerization.
The substrate concentration, enzyme addition amount, reaction time, reaction pH and other reaction conditions of the enzyme catalysis reaction are ensured to be consistent with those of the embodiment 1, the enzyme catalysis reaction is respectively carried out at the reaction temperature of 25 ℃, 40 ℃ and 55 ℃, products are analyzed through HPLC after the reaction is finished, and the glycoside conversion efficiency of the reaction is calculated. The polymerization degree of oligosaccharide in the alternan oligosaccharide of the reaction product is firstly increased and then decreased along with the increase of the reaction temperature, and the glycoside conversion efficiency is firstly increased and then decreased along with the increase of the reaction temperature. Namely, at 40 ℃, the polymerization degree and the glycoside conversion efficiency of the product reach the maximum, the reaction product is disaccharide-heptasaccharide, the glycoside conversion efficiency is 88.9%, and the chromatographic peak is shown in figure 1.
Example 2
Alternan oligosaccharides were prepared using the same strategy as in example 1, except that alternan oligosaccharides were prepared by adding 100U/g alternan sucrase, and the product was analyzed by HPLC with a conversion of 88.7% which was substantially the same as compared to adding 5U/g alternan sucrase.
Example 3
Alternan oligosaccharides were prepared using the same strategy as in example 1, except that after the second saccharification, the reaction time was 24h in a 40 ℃ water bath shaker, and the product was analyzed by HPLC with a conversion of 70.2%, which was significantly lower than the conversion for 34 h.
Example 4
Alternan oligosaccharides were prepared using the same strategy as in example 1, except that ph6.0 was adjusted at the time of secondary saccharification, and the product was analyzed by HPLC with a conversion of 74.3%.
Although the present invention has been described with reference to the preferred embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (5)
1. The method for preparing alternan oligosaccharide is characterized in that potato starch and sucrose are used as raw materials, high-temperature acid alpha-amylase, beta-amylase, pullulanase, maltogenic amylase and alternan sucrase are added in steps, and alternan oligosaccharide is prepared through the steps of pretreatment, gelatinization, liquefaction, saccharification and generation of alternan oligosaccharide, and the steps are as follows:
pretreatment and gelatinization: suspending 10% (m/v) potato starch in 50mM phosphate buffer, pH 4.5, and stirring continuously for 1.5min in boiling water bath to gelatinize the starch;
liquefaction: adding 10U/g high-temperature acidic alpha-amylase, continuously stirring in a boiling water bath for 4min, and adding 1M hydrochloric acid to adjust the pH to be below 4.0 so as to stop liquefaction;
primary saccharification: cooling the starch liquefied liquid to room temperature, adjusting the pH value to 5.2, adding 15U/g beta-amylase and 1U/g pullulanase, and reacting for 24 hours at 60 ℃;
and (3) secondary saccharification: adjusting pH of the reaction solution to 5.5, adding 9.3U/g maltogenic amylase, and reacting at 60 deg.C for 10 hr;
generation of alternan oligosaccharides: after the secondary saccharification, the enzyme is deactivated, 20 percent (m/v) of sucrose and 5U/g of alternan sucrase are sequentially added, and the reaction is carried out for 34 hours at the temperature of 40 ℃.
2. The process for the preparation of alternan oligosaccharides according to claim 1, characterized in that said maltogenic amylase is of Bacillus stearothermophilus, Bacillus licheniformis, Thermus vulgaris, Bacillus cereus or Bacillus subtilis origin.
3. A process for the preparation of alternan oligosaccharides according to claim 1 or 2, characterized in that said alternan sucrase is of the Leuconostoc citreum, leuconosteroids, Leuconostoc fallax, Leuconostoc gelidum or Oenococcus oeni origin.
4. Alternan oligosaccharide prepared according to the process of any one of claims 1 to 3.
5. Use of alternan oligosaccharides according to claim 4 for the preparation of a low-glycemic syrup, for the preparation of a medicament or for the preparation of a prebiotic.
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