SE452776B - PROCEDURE FOR THE PREPARATION OF Oligosaccharides - Google Patents
PROCEDURE FOR THE PREPARATION OF OligosaccharidesInfo
- Publication number
- SE452776B SE452776B SE8601482A SE8601482A SE452776B SE 452776 B SE452776 B SE 452776B SE 8601482 A SE8601482 A SE 8601482A SE 8601482 A SE8601482 A SE 8601482A SE 452776 B SE452776 B SE 452776B
- Authority
- SE
- Sweden
- Prior art keywords
- reaction
- process according
- carried out
- gal
- gnac
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Description
15 20 25 30 35 452 776 reaktionen förlöper väsentligt sabbare. The reaction proceeds substantially more rapidly.
Föreliggande upppfinning har sålunda till ändamål att åstad- komma ett förfarande för enzymatisk syntes av oligoeackaridet utgående fran lägre byggstenar ned till monomerer, och det för uppfinningen kännetecknande är att man i närvaro av ett glykosidas utför omvänd hydrolys genom att reaktionen utföres i en lösning innehållande substrat i hög koncentration, dvs en lösning med mot- svarande lag vattenhalt.The present invention thus has for its object to provide a process for the enzymatic synthesis of the oligoaccharide starting from lower building blocks down to monomers, and it is characteristic of the invention that in the presence of a glycosidase reverse hydrolysis is carried out by carrying out the reaction in a solution containing substrate in high concentration, ie a solution with a corresponding low water content.
Vid en föredragen utföringsform av förfarandet enligt upp- finningen utföres reaktionen vid förhöjd temperatur, exempelvis vid minst ca 30°C, och temperaturen kan vara sa hög som ända upp till temperaturer liggande nära vattnets kokpunkt, exempelvis ca 75°C.In a preferred embodiment of the process according to the invention, the reaction is carried out at elevated temperature, for example at least about 30 ° C, and the temperature can be as high as up to temperatures close to the boiling point of the water, for example about 75 ° C.
Det är lämpligt att utföra reaktionen i en lösning som in- nehàller minst ca 50 vikti substrat och särskilt minst ca 70 vikt! subetrat. Även om uppfinningen ej är inskränkt härtill utföres reak- tionen lämpligen utgående fran monomera byggstenar, varvid oli- goeackarider innehållande upp till ca 15 monomera enheter kan framställas. Det är speciellt föredraget att i enlighet med tek- niken enligt uppfinningen utföra den enzymatiska eyntesen under bildning av oligosackarider innehållande 2-5 monomera enheter. Även om uppfinningen kan tillämpas pà samtliga kända socker under användning av motsvarande glykosidas är det dock att föredra att vid reaktionen använda byggstenar utvalda bland följande socker: Ribos, arabinos, xylos, glukos, mannos (Man), galaktoe (Gal), N-acetylglukosamin (GNAc), N-acetylgalaktosamin (GalNAc), N-acetylmannosamin (ManNAc), N-acetylneuraminsyra (NeuNAc), glu- kuronsyra, galakturonsyra, mannuronsyra, iduronsyra, fucos och rhamnos.It is convenient to carry out the reaction in a solution containing at least about 50% by weight of substrate and in particular at least about 70% by weight! subetrate. Although the invention is not limited thereto, the reaction is conveniently carried out starting from monomeric building blocks, whereby oligosaccharides containing up to about 15 monomeric units can be prepared. It is especially preferred to carry out the enzymatic synthesis in accordance with the technique of the invention to form oligosaccharides containing 2-5 monomeric units. Although the invention can be applied to all known sugars using the corresponding glycosidase, it is preferred to use building blocks selected from the following sugars in the reaction: Ribose, arabinose, xylose, glucose, mannose (Man), galactoe (Gal), N-acetylglucosamine (GNAc), N-acetylgalactosamine (GalNAc), N-acetylmannosamine (ManNAc), N-acetylneuraminic acid (NeuNAc), glucuronic acid, galacturonic acid, mannuronic acid, iduronic acid, fucos and rhamnose.
Det är särskilt föredraget att vid reaktionen använda ett eller flera av följande socker: Glukos, mannos, galaktos, N-acetylglukosamin, N-acetylga- laktosamin, N-scetylneuraminsyra och fucos.It is especially preferred to use in the reaction one or more of the following sugars: Glucose, mannose, galactose, N-acetylglucosamine, N-acetylgalactosamine, N-scetylneuraminic acid and fucose.
Uppfinningen är tillämpbar även vid förfaranden där man sam- tidigt utgår från byggstenar, vilka vid en och samma reaktion in- nefattar tva eller flera av de ovan uppräknade sockertyperna, och 10 15 20 25 30 35 452 776 speciellt föredragna kombinationer av socker är härvid utvalda bland: Han-GNAc, Gal-GNAc, Gal-GalNAc, NeuNAc-Gal, NeuNAc-GNAC, NeuNAc-GalNAc, fucos-Gal och fucos-GNAC.The invention is also applicable to processes in which building blocks are simultaneously used, which in one and the same reaction include two or more of the sugars listed above, and especially preferred combinations of sugars are selected in this case. among: Male GNAc, Gal-GNAc, Gal-GalNAc, NeuNAc-Gal, NeuNAc-GNAC, NeuNAc-GalNAc, fucos-Gal and fucos-GNAC.
Uppfinningen kan naturligtvis även tillämpas för framställ- ning av oligomerer uppbyggda av en och samma monomera byggsten.The invention can of course also be applied for the production of oligomers built up of one and the same monomeric building block.
Vid användning av monomera byggstenar är det föredraget att inrikta förfarandet pa framställning av dimerer uppbyggda av en och samma typ av monomer resp, svarande mot ovannämnda särskilda kombinationer.When using monomeric building blocks, it is preferred to focus the process on the preparation of dimers composed of one and the same type of monomer or corresponding to the above-mentioned special combinations.
Reaktionen kan naturligtvis även utföras sä, att en bland- ning av oligomerer erhalles, där de enskilda oligomerslagen sedan kan separeras pa lämpligt sätt.The reaction can of course also be carried out in such a way that a mixture of oligomers is obtained, where the individual oligomer species can then be separated in a suitable manner.
Tekniken enligt uppfinningen medför väsentliga fördelar, vilka i första hand härrör fran utnyttjningen av höga substrat- koncentrationer, dvs laga vattenhalter i den använda reaktions- lösningen. Den förbättrade enzymstabilitet som uppnas vid an- vändningen av de höga substratkoncentrationer som tekniken enligt uppfinningen anvisar leder i sin tur till att reaktionen kan ut- föras vid väsentligt förhöjd temperatur. Det sammanlagda resul- tatet av dessa särdrag vid uppfinningen ger som resultat följande fördelar: a) väsentligt förhöjda produktutbyten; b) väsentligt förhöjd koncentration av den önskade produk- ten; c> väsentligt förhöjd reaktionshastighet; d) förbättrad stabilitet hos enzymet och därmed utsträckt livslängd.The technique according to the invention entails significant advantages, which primarily stem from the utilization of high substrate concentrations, ie low water contents in the reaction solution used. The improved enzyme stability obtained by the use of the high substrate concentrations indicated by the technique according to the invention in turn leads to the reaction being able to be carried out at a substantially elevated temperature. The overall result of these features of the invention results in the following advantages: a) significantly increased product yields; b) significantly increased concentration of the desired product; c> significantly increased reaction rate; d) improved stability of the enzyme and thus extended service life.
Som exempel pa tillämpning av tekniken enligt uppfinningen kan nämnas framställning av oligoeackarider utgående fran monomera enheter av mannos. Vid uppvärmning till ca 75°C kan mannos lösas till mycket hög koncentration, mer än 85 vikt%, och en sadan hög- koncentrerad mannoelösning kan bibehallas vid rumstemperatur under någon timme innan sockerkristallisation insätter. I anslutning till uppfinningens tillkomst gjordes nu den förvånande upptäckten att det använda enzymet, mannosidas, accepterade denna höga sub- stratkoncentration utan att påverkas negativt. 10 15 20 25 3U 35 452 776 Eftersom en substratlösning innehållande denna höga koncen- tration av socker lätt underkastas utkristallisation av sockret är det lämpligt att höja temperaturen, och det visar sig härvid helt överraskande att enzymet icke påverkas av den höga temperaturen.Examples of the application of the technique according to the invention are the preparation of oligoaccharides starting from monomeric units of mannose. When heated to about 75 ° C, mannose can be dissolved to a very high concentration, more than 85% by weight, and such a highly concentrated mannol solution can be maintained at room temperature for a few hours before sugar crystallization begins. In connection with the advent of the invention, the surprising discovery was now made that the enzyme used, mannosidase, accepted this high substrate concentration without being adversely affected. 10 15 20 25 3U 35 452 776 Since a substrate solution containing this high concentration of sugar is easily subjected to crystallization of the sugar, it is suitable to raise the temperature, and it turns out quite surprisingly here that the enzyme is not affected by the high temperature.
Reaktionen kunde sålunda genomföras vid ca 75°C, varvid reak- tionshaetigheten var ca 30 gånger större än vid rumstemperatur.The reaction could thus be carried out at about 75 ° C, the reaction rate being about 30 times greater than at room temperature.
Uppenbarligen medför den höga substrathalten att enzymet stabi- liseras så att någon värmeinaktivering icke uppträder.Obviously, the high substrate content means that the enzyme is stabilized so that no heat inactivation occurs.
Beträffande använda enzymer användes naturligtvis eadana som ger önskad produkt och som motsvarar den använda kolhydrattypen.For enzymes used, of course, eadana is used which gives the desired product and which corresponds to the type of carbohydrate used.
Vid framställning av exempelvis oligosackarider av mannos kan sa- lunda användas lämpligt mannosidas, exempelvis u-mannosidas.Thus, in the preparation of, for example, oligosaccharides of mannose, suitable mannosidase can be used, for example u-mannosidase.
Uppfinningen kommer nu att illustreras närmare genom icke inskränkande exempel. Dessa illustrerar framställningen av nagra olika typer av oligosackarider under tillämpning av tekniken en- ligt uppfinningen. I exemplen angivna procenttal avser vikten om ej annat anges.The invention will now be further illustrated by non-limiting examples. These illustrate the preparation of some different types of oligosaccharides using the technique according to the invention. The percentages given in the examples refer to the weight unless otherwise stated.
EXEMPEL 1 Reverserino med ß-qalaktosidas fràn Eicoli i 36% qalaktos. 0,8 g galaktos och 1,2 g H20 upphettades i vattenbad tills all galaktos upplöste, och lösningen tilläts därefter svalna till rumstemperatur. Till 1,5 ml av galaktoslösningen sattes 20/ul 1M fosfatbuffert, pH 7,2 och 0,15 ml enzymlösning innehållande 185 enzymenheter. Blandningen inkuberades vid rumstemperatur, och pro- dukterna detekterades med HPLC. Efter det att jämvikt uppnåtts, avbröts reaktionen genom upphettning på kokande vattenbad 10 min., och en slutbestämning av utbytet gjordes medelst GC. Utbytet en- ligt GC blev 10% disackarid (w/w).EXAMPLE 1 Reverserino with β-galactosidase from Eicoli in 36% qalactose. 0.8 g of galactose and 1.2 g of H 2 O were heated in a water bath until all the galactose dissolved, and the solution was then allowed to cool to room temperature. To 1.5 ml of the galactose solution was added 20 .mu.l of 1M phosphate buffer, pH 7.2 and 0.15 ml of enzyme solution containing 185 enzyme units. The mixture was incubated at room temperature, and the products were detected by HPLC. After equilibrium was reached, the reaction was quenched by heating on a boiling water bath for 10 minutes, and a final determination of the yield was made by GC. The yield according to GC was 10% disaccharide (w / w).
EXEHPEL 2 - als t sidas från E coli ut aende från alaktos och N-acetylgalaktgsamig, 9 mg galaktos upplöstes i 21 mg 20mM fosfatbuffert, pH 7,5, Reverserin med genom upphettning på kokande vattenbad. Efter avevalning till rumstemperatur tillsattes 24 mg GalNAc under omrörning. Frystor- kat, rent ßgalaktosidae (450 enzymenheter (U)) tillsattes till 200 U/ml. 10 15 20 25 30 35 452 776 I Efter 2 dygn avbröts reaktionen genom upphettning pa kokande vattenbad i 5 min. Analyser med GC-MS visade att 5% galaktos (w/w) baserat pa den totala sockermängden hade bundits in som disacka- rid. Av detta förelag 2-3! som Gal-GalNAc. Endast 1,6-isomeren kunde aterfinnas.EXAMPLE 2 - Aside from E. coli from lactose and N-acetyl galactose, 9 mg of galactose was dissolved in 21 mg of 20 mM phosphate buffer, pH 7.5, Reverserin with by heating on boiling water bath. After dehydration to room temperature, 24 mg of GalNAc was added with stirring. Freeze-dried, pure ßgalactosidae (450 enzyme units (U)) was added to 200 U / ml. After 2 days, the reaction was quenched by heating on a boiling water bath for 5 minutes. Analyzes with GC-MS showed that 5% galactose (w / w) based on the total amount of sugar had been bound as disaccharide. By this publisher 2-3! as Gal-GalNAc. Only the 1,6-isomer could be found.
EXEMEEL 3 Reversering stor skala i 83% maggog, 5 g mannos upplöstes i 0,883 g buffert (20 mM fosfat-citrat, 50 mM KCl, 1 mM 2nCl, och 0,02% azid) genom upphettning pa kokande vattenbad i ett provrör med tättslutande skruvlock, och lösningen tilläts sedan svalna nagot. 0,3 ml<1-mannosidas fran jack bean i buffert (130 enzymenheter/ml) tillsattes, och blandningen inku- berades vid 75°C. Aktiviteten i reaktionsblandningen var efter 1 dygn uppe i 6 U/ml och höll sig oförändrad under tiden reaktionen tilläts fortgå. Produkter detekterades med HPLC.EXAMPLE 3 Large scale reversal in 83% maggog, 5 g mannose was dissolved in 0.883 g buffer (20 mM phosphate citrate, 50 mM KCl, 1 mM 2nCl, and 0.02% azide) by heating on a boiling water bath in a tight-fitting test tube. screw cap, and the solution was then allowed to cool slightly. 0.3 ml <1-mannosidase from jack bean in buffer (130 enzyme units / ml) was added, and the mixture was incubated at 75 ° C. The activity in the reaction mixture was after 6 days up to 6 U / ml and remained unchanged while the reaction was allowed to proceed. Products were detected by HPLC.
Efter 3 dygn avbröts reaktionen genom upphettning pa kokande vattenbad, och slutgiltig analys och utbytesbestämning utfördes med GC-MS. Utbytet av di-, tri-, tetra-, och högre oligosackarider blev 30, 25, 10 resp. 5%. .u EXEMPEL 4 Reversering i mannos: Utbvtesbeetämgigg vid olika mannoskoncentrg- tioner, Hannes, buffert (se Exempel 3 ovan), och enzymlösning (ca 150 enzymenheter/ml) vigdes upp och blandades , så att koncentra- tionen av mannos blev 20, 30, 55 resp. 85! (w/w>. I fallet med 85% mannos krävdes upphettning på kokande vattenbad av mannos och buf- fert innan enzymet tillsattes för att mannosen skulle lösa sig, medan i de övriga fallen mannosen kunde lösas vid rumstemperatur.After 3 days, the reaction was quenched by heating on a boiling water bath, and final analysis and yield determination were performed by GC-MS. The yield of di-, tri-, tetra-, and higher oligosaccharides was 30, 25, 10, respectively. 5%. EXAMPLE 4 Reversal in mannose: Replacement reaction at different mannose concentrations, Hannes, buffer (see Example 3 above), and enzyme solution (about 150 enzyme units / ml) were weighed and mixed so that the concentration of mannose was 20, 30 , 55 resp. 85! (w / w>. In the case of 85% mannose, heating on a boiling water bath of mannose and buffer was required before the enzyme was added for the mannose to dissolve, while in the other cases the mannose could be dissolved at room temperature.
Proverna inkuberades vid 50°C, och bildningen av disackarider följdes med HPLC. Da mängden disackarid slutat öka i resp. prov avbröts reaktionen genom upphettning på kokande vattenbad i 12 min.The samples were incubated at 50 ° C, and the formation of disaccharides was monitored by HPLC. When the amount of disaccharide stopped increasing in resp. sample, the reaction was stopped by heating on a boiling water bath for 12 minutes.
En slutbestämning av utbytet gjordes medelst GC. Utbytet av disackarider i 20, 30, 55 och 85% mannos blev 22, 25, 31, resp. 39% baserat pa den totala sockermângden. 452 776 Det bör observeras att föteliggande uppfinning ingalunda är inskränkt till de i ovanstående exempel angivna eockerarterna utan att den kan tillämpas pà alla kända typer av socker under använd- ning av motsvarande glykoeidae som enzym.A final determination of the yield was made by GC. The yield of disaccharides in 20, 30, 55 and 85% mannose was 22, 25, 31, respectively. 39% based on the total amount of sugar. It should be noted that the present invention is by no means limited to the eukaryotes listed in the above examples without being applicable to all known types of sugar using the corresponding glycoeidae as an enzyme.
Claims (11)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8601482A SE452776B (en) | 1986-04-02 | 1986-04-02 | PROCEDURE FOR THE PREPARATION OF Oligosaccharides |
| JP50214387A JPS63502900A (en) | 1986-04-02 | 1987-04-01 | Method for producing oligosaccharides |
| PCT/SE1987/000170 WO1987005936A1 (en) | 1986-04-02 | 1987-04-01 | Process for the manufacture of oligosaccharides |
| EP19870902186 EP0410963A1 (en) | 1986-04-02 | 1987-04-01 | Process for the manufacture of oligosaccharides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8601482A SE452776B (en) | 1986-04-02 | 1986-04-02 | PROCEDURE FOR THE PREPARATION OF Oligosaccharides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8601482D0 SE8601482D0 (en) | 1986-04-02 |
| SE8601482L SE8601482L (en) | 1987-10-03 |
| SE452776B true SE452776B (en) | 1987-12-14 |
Family
ID=20364027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8601482A SE452776B (en) | 1986-04-02 | 1986-04-02 | PROCEDURE FOR THE PREPARATION OF Oligosaccharides |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0410963A1 (en) |
| JP (1) | JPS63502900A (en) |
| SE (1) | SE452776B (en) |
| WO (1) | WO1987005936A1 (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63109789A (en) * | 1986-10-27 | 1988-05-14 | Yakult Honsha Co Ltd | Production of oligosaccharide |
| SE466403B (en) * | 1988-03-24 | 1992-02-10 | Kurt G I Nilsson | SAID TO SYNTHETIZE Oligosaccharides |
| FR2629985B1 (en) * | 1988-04-14 | 1994-01-21 | Roussel Uclaf | APPLICATION AS LOW-CALORIC SUGAR PRODUCTS OF FRUCTOSYLATED OLIGOSACCHARIDES AND FOODS, DIETETIC PRODUCTS AND BEVERAGES CONTAINING THEM |
| SE465516B (en) * | 1989-08-18 | 1991-09-23 | Kurt G I Nilsson | MADE TO MAKE A OLIGOSACCARIDE COMPOUND WHICH GLYCOSIDAS FROM A MOLLUSK IS USED |
| SE9000758L (en) * | 1990-03-02 | 1991-09-03 | Kurt G I Nilsson | BIOCHEMICAL PROCEDURE |
| SE9102292L (en) * | 1991-08-06 | 1993-02-07 | Kurt G I Nilsson | ENZYMATIC METHOD |
| US6284494B1 (en) | 1995-12-12 | 2001-09-04 | The University Of British Columbia | Methods and compositions for synthesis of oligosaccharides using mutant glycosidase enzymes |
| US5716812A (en) * | 1995-12-12 | 1998-02-10 | The University Of British Columbia | Methods and compositions for synthesis of oligosaccharides, and the products formed thereby |
| CA2165041C (en) * | 1995-12-12 | 2005-07-05 | The University Of British Columbia | Methods and compositions for synthesis of oligosaccharides, and the products formed thereby |
| WO1997021822A2 (en) * | 1995-12-12 | 1997-06-19 | The University Of British Columbia | Methods and compositions for synthesis of oligosaccharides using mutant glycosidase enzymes |
| US20010051349A1 (en) | 2000-02-17 | 2001-12-13 | Glycominds Ltd. | Combinatorial complex carbohydrate libraries and methods for the manufacture and uses thereof |
| US7999003B2 (en) | 2003-08-26 | 2011-08-16 | Mannatech, Incorporated | Antioxidant compositions and methods thereto |
| MX2010009479A (en) | 2008-02-29 | 2010-12-07 | Afexa Life Sciences Inc | Activation of innate and adaptive immune responses by a ginseng extract. |
-
1986
- 1986-04-02 SE SE8601482A patent/SE452776B/en not_active IP Right Cessation
-
1987
- 1987-04-01 WO PCT/SE1987/000170 patent/WO1987005936A1/en not_active Application Discontinuation
- 1987-04-01 EP EP19870902186 patent/EP0410963A1/en not_active Withdrawn
- 1987-04-01 JP JP50214387A patent/JPS63502900A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63502900A (en) | 1988-10-27 |
| EP0410963A1 (en) | 1991-02-06 |
| SE8601482L (en) | 1987-10-03 |
| SE8601482D0 (en) | 1986-04-02 |
| WO1987005936A1 (en) | 1987-10-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE452776B (en) | PROCEDURE FOR THE PREPARATION OF Oligosaccharides | |
| AU2017256470B2 (en) | Method for producing 2'-fucosyllactose by using Corynebacterium glutamicum | |
| TWI510627B (en) | Large scale enzymatic synthesis of oligosaccharides | |
| Huang et al. | Microheterogeneity and paucidispersity of glycoproteins: Part I. The carbohydrate of chicken ovalbumin | |
| CA2488853C (en) | Process and materials for production of glucosamine and n-acetylglucosamine | |
| CN111377983B (en) | Preparation method of beta-nicotinamide mononucleotide | |
| US20230212628A1 (en) | Production of Sialylated Oligosaccharide in Host Cells | |
| KR102014925B1 (en) | Production method of 2'-fucosyllactose with fucosyltransferase from Pseudopedobacter saltans | |
| DE60208562T2 (en) | PROCESS FOR THE PRODUCTION OF TAGATOSIS | |
| EP3999635A1 (en) | Production of fucosyllactose in host cells | |
| DK172544B1 (en) | Process for Preparation of 1-O-alpha-D-glucopyranosido-D-fructose by enzymatic conversion of sucrose | |
| EP0096547B1 (en) | Process for preparing uridine diphosphate-n-acetylgalactosamine | |
| CN109321508B (en) | Genetic engineering bacterium for producing hepanosan and application thereof | |
| US10281460B2 (en) | Polyporus squamosus-derived recombinant lectin specific for sialic acid linkage | |
| EP0259598A2 (en) | Process for the enzymatic synthesis of a trisaccharide containing N-acetylneuraminic acid | |
| Markovitz et al. | Effect of sodium sulfate and magnesium sulfate on heteropolysaccharide synthesis in gram-negative soil bacteria | |
| Gatreddi et al. | Ribokinase from Leishmania donovani: purification, characterization and X-ray crystallographic analysis | |
| KR102466543B1 (en) | Method for preparing turanose | |
| JPH07508413A (en) | Purified sucrose-synthase, its production method and its use | |
| JP4910091B2 (en) | 4-position halogenated galactose-containing sugar chain and its application | |
| SU1319503A1 (en) | Method of obtaining tritium-labelled desoxy-(5,6-3h2)cytidin-5ъ-mono- and triphosphates | |
| EP3757209A1 (en) | Enzymatic production of levan-based, prebiotic fructooligosaccharides | |
| CN116904537A (en) | Method for preparing adenosine diphosphate pure product by using biological enzyme | |
| JP2021087439A (en) | Method for preparing rebaudioside j using enzymatic method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
Ref document number: 8601482-6 Format of ref document f/p: F |
|
| NUG | Patent has lapsed |
Ref document number: 8601482-6 Format of ref document f/p: F |