CN106591397A - Method for preparing lactose-N-disaccharide - Google Patents
Method for preparing lactose-N-disaccharide Download PDFInfo
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- CN106591397A CN106591397A CN201611063933.0A CN201611063933A CN106591397A CN 106591397 A CN106591397 A CN 106591397A CN 201611063933 A CN201611063933 A CN 201611063933A CN 106591397 A CN106591397 A CN 106591397A
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- 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
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- 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
- C12P19/24—Preparation of compounds containing saccharide radicals produced by the action of an isomerase, e.g. fructose
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Abstract
The invention discloses a method for preparing lactose-N-disaccharide. 1-phosphate galactose, N-acetyl glucosamine, lactose-N-disaccharide phosphorylase and phosphate buffer are placed in the same reaction system and mixed to synthesize the objective product lactose-N-disaccharide. The 1-phosphate galactose is prepared by using starch, sucrose, dextrin and other cheap raw materials. The simple method is used for one-step synthesis of the objective product lactose-N-disaccharide, the preparation cost of the product is low, and the practical value is high.
Description
Technical field
The present invention relates to oligosaccharide synthesis field, and in particular to a kind of preparation method of Lactose-N- disaccharide.
Background technology
The class breast milk oligosaccharide contained in breast milk be nature others mammal milk in do not contained, it is special
Oligosaccharide, research in recent years shows which is the narrow spectrum food source of bacillus bifiduss, do not utilized by other strains.In pure breast milk
In fed infant, bacillus bifiduss account for more than the 90% of intestinal bacteria total amount, even as high as 99%.Though have one in the market
A little oligosaccharide can increase the quantity of bacillus bifiduss in baby intestinal as prebioticses in being added to milk, but due to its chemistry
The limitation of structure so that its activity cannot be mentioned in the same breath with breast milk oligosaccharide with effect, it is impossible to simulate whole work(of breast milk oligosaccharide
Energy.And propagation non-selectivity of the oligosaccharide of these synthetic to enteric microorganism, in addition to bacillus bifiduss, can also breed other
Various intestinal bacteria, and it is not beneficial bacteria of intestinal tract that some antibacterials have, has no benefit to health.
Oligosaccharide in breast milk has kind more than 130, and wherein Lactose-N- disaccharide (Gal- β 1,3-GlcNAc) is that breast milk oligosaccharide is important
One of core structure part, and the intake of infant intestinal bifidobacteria the direct energy body of metabolism breast milk oligosaccharide.Baby
After disengaging parent starts to suck breast milk, bacillus bifiduss are colonized propagation rapidly in intestinal, most important in formation infant intestinal
It is the flora of most advantage.Bacillus bifiduss are played a very important role in intestinal microecology balance, are sticked by being colonized in body intestinal
Theca cell participates in a series of physiological process such as immunity of organism, nutrition, digestion and protection, defines symbiosiss with body.Bifid
Bacillus as the dominant microflora in intestinal, with Ant agonism, barrier action, Hepatocyte protection, trophic function and immunity
The several functions characteristics such as effect.Dysentery and other antibacterials with breast-fed babies is far with the sickness rate of viral infectious disease
Less than the milk fed infant such as milk, its reason is precisely due to intestinal based on breast-fed babies' intestinal bifidobacteria
The field planting speed and quantity of group is far above other milk supply institute fed infants.
The content of the invention
It is an object of the present invention to provide a kind of preparation method of Lactose-N- disaccharide, prepared oligosaccharide structure is Gal- β 1,3-
GlcNAc, i.e. Lactose-N- disaccharide.Using the method for the present invention can also synthesize it is all containing and/or with Lactose-N- disaccharide as bone
The oligosaccharide or polysaccharide of bone construction.
The technical solution used in the present invention is：
A kind of preparation method of Lactose-N- disaccharide, by galactose 1-phosphate, N-acetyl-glucosamine, Lactose-N- disaccharide phosphoric acid
Change enzyme and phosphate buffer is placed in same reaction system while immixture synthesis purpose product Lactose-N- disaccharide.
Described preparation method, the pH value of the phosphate buffer is 3-9, and concentration is 1 μM of -2M；The reaction system
Condition：Temperature 5-50 DEG C, response time 2min-1 month.
Described preparation method, in the reaction system, the addition of two saccharophosphorylases of Lactose-N- is 0.01-
10000U。
Described preparation method, in the reaction system, the addition of galactose 1-phosphate is 1 μM of -2M；The N- acetyl
The addition of glycosamine is 1 μM of -2M.
Described preparation method, the galactose 1-phosphate be with 1- phosphate-dextroses, udp glucose or
Diphosphonic acid urine nucleoside galactose is raw material, in UDPG pbosphohexose uridyltransferase and UDPG epimerism
The galactose 1-phosphate synthesized under enzyme effect.
Described preparation method, the 1- phosphate-dextroses are obtained by the phosphorylated enzyme decomposition of saccharine material.
Described preparation method, by saccharine material, phosphorylase, UDPG pbosphohexose uridyltransferase,
UDPG epimerase, two saccharophosphorylases of Lactose-N-, N-acetyl-glucosamine, phosphate buffer are placed in same reaction
Purpose product Lactose-N- the disaccharide of immixture synthesis simultaneously in system.
Described preparation method, the saccharine material are udp glucose, diphosphonic acid urine nucleoside galactose, sugarcane
Sugar, Fructus Hordei Germinatus oligose, dextrin, starch, cellulose oligosaccharide, fibre-bearing disaccharide, cellulose, laminari-oligo saccharide, laminarin, glucosan,
One or more combinations in glycogen.
Described preparation method, the phosphorylase are glucosan phosphorylase, starch phosphorylase, glycogen phos
One kind in enzyme, maltodextrin phosphorylase, sucrose phosphorylase, laminaribiose phosphorylase, cellobiose phosphorylase or
Two or more combinations.
The invention has the advantages that：
Oligosaccharide structure synthesized by the present invention is Gal- β 1,3-GlcNAc, i.e. Lactose-N- disaccharide.Using the side of the present invention
Method can also synthesize it is all containing and/or oligosaccharide or polysaccharide with Lactose-N- disaccharide as skeleton.The present invention can utilize honest and clean
The saccharine materials such as the starch of valency, sucrose, dextrin, by simple method one-step synthesis purpose product Lactose-N- disaccharide, product system
Standby low cost, practical value are high.
In the present invention, used raw material has saccharine material, phosphoric acid, phosphorylase (containing glucosan phosphorylase, starch phosphorus
Acidifying enzyme, glycogen phosphorylase, maltodextrin phosphorylase, sucrose phosphorylase, laminaribiose phosphorylase, cellobiose phosphorus
Acidifying enzyme, two saccharophosphorylases of Lactose-N- etc.), UDPG epimerase, UDPG pbosphohexose uridnine acyl turn
Move enzyme.
In the present invention used saccharine material include galactose 1-phosphate, Cori's eater Cori, N-acetyl-glucosamine, two
Uridin phosphoric acid glucose, diphosphonic acid urine nucleoside galactose, sucrose, Fructus Hordei Germinatus oligose, dextrin, starch, cellulose oligosaccharide, fiber
Element, laminari-oligo saccharide, laminarin, glucosan, glycogen and other contain (1 → 3) glucose structural units or (1 → 4) Fructus Vitis viniferae
Derivant of oligosaccharide or polysaccharide or saccharide of sugared structural units etc..The source of saccharic has no particular limits, can be it is commercially available,
Can be extract from the tissue such as the plant of nature, animal, microorganism, or by chemistry or the method people of biology
Work synthesis.
The source of the enzyme used in the present invention has no particular limits, and can be the antibacterial of nature, can also be ferment
Extract in the microbial cells such as female or funguses and obtain；Can be produced by genetic engineering bacterium by gene recombinaton and obtained；Can be
By nature plant tissue or animal tissue in extract and obtain.The product form of enzyme is also not particularly limited, and can be solid, powder
End, liquid or the immobilized enzyme being fixed on by method physically or chemically on carrier；Enzyme can be commercially available commodity, also may be used
Being the product of enterprise or custom setup.
The present invention synthetic method can be with galactose 1-phosphate and N-acetyl-glucosamine as the raw material that sets out, Lactose-
Synthesize Lactose-N- disaccharide in the presence of bis- saccharophosphorylases of N-.
The present invention synthetic method can also be 1- phosphate-dextroses, udp glucose (or diphosphonic acid urine core
Glycosides galactose), N-acetyl-glucosamine, UDPG pbosphohexose uridyltransferase, UDPG epimerase and
Two saccharophosphorylases of Lactose-N- collective effect synthesis Lactose-N- disaccharide under same mixed system.The method be with 1- phosphoric acid-
Glucose is aided with udp glucose (or diphosphonic acid urine nucleoside galactose) for raw material, in UDPG pbosphohexose
Synthesize galactose 1-phosphate under uridyltransferase and UDPG epimerism enzyme effect；Galactose 1-phosphate again with N- second
Acyl glycosamine is the raw material that sets out, and synthesizes Lactose-N- disaccharide in the presence of two saccharophosphorylases of Lactose-N-.
The synthetic method of the present invention is can also be with sucrose, starch, Fructus Hordei Germinatus oligose, dextrin, glucosan, glycogen, diphosphonic acid
Urine nucleoside glucose, the combination of one or more of the diphosphonic acid urine above-mentioned saccharine material such as nucleoside galactose, phosphorylase
The combination of one or more and UDPG pbosphohexose uridyltransferase, two saccharophosphorylases of Lactose-N-, UDP-
Glucose epimerase and N-acetyl-glucosamine are in same reaction system while immixture, closes in same reaction system
Into purpose product Lactose-N- disaccharide.The method is with the above-mentioned sugar such as sucrose, starch, Fructus Hordei Germinatus oligose, dextrin, glucosan, glycogen
The combination of one or more of matter raw material, phosphorylated enzyme decomposition obtain 1- phosphate-dextroses；Phosphorylase can be above-mentioned phosphorus
The combination of one or more of acidifying enzyme apoplexy due to endogenous wind；1- phosphate-dextroses are turned with follow-up UDPG pbosphohexose uridnine acyl
Move enzyme, two saccharophosphorylases of Lactose-N-, UDPG epimerase, udp glucose (or diphosphonic acid urine core
Glycosides galactose) and N-acetyl-glucosamine collective effect synthesis purpose product Lactose-N- disaccharide.Raw materials used to be easy to get, method is simple,
Mild condition, preparation cost are low, are suitable to wide popularization and application.
Specific embodiment
A kind of preparation method of Lactose-N- disaccharide
By the galactose 1-phosphate of 1 μM of -2M, 1 μM of -2M N-acetyl-glucosamine, 1 μM of -2M phosphate buffer (pH 3-9),
After two saccharophosphorylases of Lactose-N- of 0.01-10000U react 2min-1 month at 5-50 DEG C, you can generate Lactose-N- two
Sugared (Gal- β 1,3-GlcNAc), structural formula are (I).Reactant liquor is concentrated, refined, pure Lactose-N- two is obtained after crystallization
Sugar product.Its molecular weight of product Jing Mass Spectrometer Method is 383, and Jing magnetic resonance detection confirms that its structure is Lactose-N- disaccharide.Its
The yield of Lactose-N- disaccharide can reach 87%.
A kind of preparation method of 1 Lactose-N- disaccharide of embodiment
By 10mM sucrose, 10mM udp glucoses, the sucrose phosphorylase of 50U, UDPG hexose phosphorus
Sour uridyltransferase, UDPG epimerase, two saccharophosphorylases of Lactose-N- of 100U, the N- acetyl Portugal of 10mM
Osamine and 100mM phosphate buffers (pH 6-7), are placed in same reaction system, after reaction system is reacted 10 days at 30 DEG C,
Lactose-N- disaccharide can be generated.Reactant liquor is concentrated, refined, pure two sugar products of Lactose-N- are obtained after crystallization.Product
Its molecular weight of Jing Mass Spectrometer Method is 383, and Jing magnetic resonance detection confirms that its structure is Lactose-N- disaccharide.Lactose-N- disaccharide
Yield is up to 80%.
A kind of preparation method of 2 Lactose-N- disaccharide of embodiment
By the diphosphonic acid urine nucleoside galactose of the sucrose of 1M, 1M, the fixation being fixed on alginate carrier of 10000U
The sucrose phosphorylase of change, UDPG epimerase, UDPG pbosphohexose uridyltransferase, 10000U are newborn
Two saccharophosphorylases of sugar-N-, the N-acetyl-glucosamine of 2M and 1M phosphate buffers (pH 8-9), are placed in same reaction system,
After reaction system reacts certain hour 20min at 50 DEG C, you can generate Lactose-N- disaccharide.Reactant liquor is concentrated, refined, knot
Pure two sugar products of Lactose-N- are obtained after crystalline substance.Its molecular weight of product Jing Mass Spectrometer Method is 383, and Jing magnetic resonance detection
Confirm that its structure is Lactose-N- disaccharide.The yield about 3% of Lactose-N- disaccharide.
A kind of preparation method of 3 Lactose-N- disaccharide of embodiment
By 50 μM of Fructus Hordei Germinatus oligoses, 2 μM of udp glucoses, 200U the fixation being fixed on alginate carrier
The maltodextrin phosphorylase of change, UDPG epimerase, UDPG pbosphohexose uridyltransferase,
Two saccharophosphorylases of 5000U Lactose-N-, 50 μM of N-acetyl-glucosamine and 2M phosphate buffers (pH 5-6), are placed in same anti-
In answering system, after this reaction system is reacted 15 days at 30 DEG C, you can generate Lactose-N- disaccharide.Reactant liquor is concentrated, refined,
Pure two sugar products of Lactose-N- are obtained after crystallization.Its molecular weight of product Jing Mass Spectrometer Method is 383, and the inspection of Jing nuclear magnetic resonance, NMR
Survey and confirm that its structure is Lactose-N- disaccharide.The yield of Lactose-N- disaccharide is up to 83%.
A kind of preparation method of 4 Lactose-N- disaccharide of embodiment
By 0.5% starch, 2M dextrin, 1M udp glucoses, 2000U starch phosphorylase, the wheat of 1000U
Bud dextrin phosphorylase, UDPG epimerase, UDPG pbosphohexose uridyltransferase, 7000U Lactose-
Bis- saccharophosphorylases of N-, the N-acetyl-glucosamine of 3M and 100mM phosphate buffers (pH 7-8), are placed in same reaction system,
After reaction system is reacted 1 month at 10 DEG C, you can generate Lactose-N- disaccharide.Reactant liquor is concentrated, refined, can obtain after crystallization
To pure two sugar products of Lactose-N-.Its molecular weight of product Jing Mass Spectrometer Method is 383, and Jing magnetic resonance detection confirms its knot
Structure is Lactose-N- disaccharide.The yield of Lactose-N- disaccharide is up to 87%.
A kind of preparation method of 5 Lactose-N- disaccharide of embodiment
2M fibre-bearing disaccharide, 500m M laminaribioses, 50 μM of udp glucoses, 10000U are fixed on into Buddhist nun
The laminaribiose phosphorylase of cellobiose phosphorylase, 3000U on imperial film, UDPG epimerase, UDP- Portugals
Grape sugar pbosphohexose uridyltransferase, two saccharophosphorylases of 2000U Lactose-N-, the N-acetyl-glucosamine of 2.5M and 20mM phosphorus
Acid buffer (pH 3-4), is placed in same reaction system, after this reaction system is reacted 20 days at 50 DEG C, you can generate breast
Sugar-N- disaccharide.Reactant liquor is concentrated, refined, pure two sugar products of Lactose-N- are obtained after crystallization.Product Jing Mass Spectrometer Method
Its molecular weight is 383, and Jing magnetic resonance detection confirms that its structure is Lactose-N- disaccharide.The yield of Lactose-N- disaccharide reaches
85%.
A kind of preparation method of 6 Lactose-N- disaccharide of embodiment
By 1.0% glycogen, 50mM udp glucoses, the glycogen phosphorylase of 100U, UDPG difference to
Isomerase, UDPG pbosphohexose uridyltransferase, two saccharophosphorylases of 90U Lactose-N-, the N-acetyl-glucosamine of 1M
With 200mM phosphate buffers (pH 5-6), it is placed in same reaction system, after this reaction system is reacted 5 days at 25 DEG C, you can
Generate Lactose-N- disaccharide.Reactant liquor is concentrated, refined, pure two sugar products of Lactose-N- are obtained after crystallization.Product Jing matter
Spectrum detects that its molecular weight is 383, and Jing magnetic resonance detection confirms that its structure is Lactose-N- disaccharide.The yield of Lactose-N- disaccharide
Up to 45%.
A kind of preparation method of 7 Lactose-N- disaccharide of embodiment
By 0.1% beta glucan, 10mM udp glucoses, the glucosan phosphorylase of 100U, UDP- Fructus Vitis viniferaes
Sugared epimerase, UDPG pbosphohexose uridyltransferase, two saccharophosphorylases of 100U Lactose-N-, the N- of 0.1M
Acetylglucosamine and 100mM phosphate buffers (pH 4-5), are placed in same reaction system, and this reaction system is reacted at 35 DEG C
After 12 hours, you can generate Lactose-N- disaccharide.Reactant liquor is concentrated, refined, pure Lactose-N- disaccharide is obtained after crystallization
Product.Its molecular weight of product Jing Mass Spectrometer Method is 383, and Jing magnetic resonance detection confirms that its structure is Lactose-N- disaccharide.Breast
The yield about 10% of sugar-N- disaccharide.
Claims (9)
1. a kind of preparation method of Lactose-N- disaccharide, it is characterised in that by galactose 1-phosphate, N-acetyl-glucosamine, Lactose-
Bis- saccharophosphorylases of N- and phosphate buffer are placed in same reaction system while immixture synthesis purpose product Lactose-N- two
Sugar.
2. preparation method as claimed in claim 1, it is characterised in that the pH value of the phosphate buffer is 3-9, and concentration is 1 μ
M-2M；The condition of the reaction system：Temperature 5-50 DEG C, response time 2min-1 month.
3. preparation method as claimed in claim 1, it is characterised in that two saccharophosphorylases of Lactose-N- in the reaction system
Addition be 0.01-10000U.
4. preparation method as claimed in claim 1, it is characterised in that the addition of galactose 1-phosphate in the reaction system
For 1 μM of -2M；The addition of the N-acetyl-glucosamine is 1 μM of -2M.
5. the preparation method as described in any one of claim 1-4, it is characterised in that the galactose 1-phosphate is with 1- phosphorus
Acid-glucose, udp glucose or diphosphonic acid urine nucleoside galactose is raw material, is urinated in UDPG pbosphohexose
The galactose 1-phosphate synthesized under glycosides acyltransferase and UDPG epimerism enzyme effect.
6. preparation method as claimed in claim 5, it is characterised in that the 1- phosphate-dextroses are by saccharine material Jing phosphorus
Acidifying enzyme decomposes what is obtained.
7. preparation method as claimed in claim 6, it is characterised in that by saccharine material, phosphorylase, UDPG hexose
Phosphate uridyl-transferase, UDPG epimerase, two saccharophosphorylases of Lactose-N-, N-acetyl-glucosamine, phosphoric acid delay
Rush liquid to be placed in same reaction system while immixture synthesis purpose product Lactose-N- disaccharide.
8. preparation method as claimed in claims 6 or 7, it is characterised in that the saccharine material is that diphosphonic acid urinates nucleoside Fructus Vitis viniferae
Sugar, diphosphonic acid urine nucleoside galactose, sucrose, Fructus Hordei Germinatus oligose, dextrin, starch, cellulose oligosaccharide, fibre-bearing disaccharide, cellulose, sea
With one or more combinations in oligosaccharide, laminarin, glucosan, glycogen.
9. preparation method as claimed in claims 6 or 7, it is characterised in that the phosphorylase is glucosan phosphorylase, forms sediment
Powder phosphorylase, glycogen phosphorylase, maltodextrin phosphorylase, sucrose phosphorylase, laminaribiose phosphorylase, fiber two
One or more combinations in saccharophosphorylase.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201611063933.0A CN106591397A (en) | 2016-11-28 | 2016-11-28 | Method for preparing lactose-N-disaccharide |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201611063933.0A CN106591397A (en) | 2016-11-28 | 2016-11-28 | Method for preparing lactose-N-disaccharide |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111903766A (en) * | 2020-08-10 | 2020-11-10 | 沈阳农业大学 | Infant formula milk powder and preparation method thereof |
| WO2021082352A1 (en) * | 2019-10-31 | 2021-05-06 | 烟台华康荣赞生物科技有限公司 | Method for synthesizing lacto-n-biose |
-
2016
- 2016-11-28 CN CN201611063933.0A patent/CN106591397A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| MAMORU NISHIMOTO等: "Practical Preparation of Lacto-N-biose I, a Candidate for the Bifidus Factor in Human Milk", 《BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY》 * |
| MOTOMITSU KITAOKA等: "Novel putative galactose operon involv- ing lacto-N-biose phosphorylase in Bifidobacterium longum", 《APPLIED AND ENVIRONMENTAL MICROBIOLOGY》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021082352A1 (en) * | 2019-10-31 | 2021-05-06 | 烟台华康荣赞生物科技有限公司 | Method for synthesizing lacto-n-biose |
| CN111903766A (en) * | 2020-08-10 | 2020-11-10 | 沈阳农业大学 | Infant formula milk powder and preparation method thereof |
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