CN110734945A - method for synthesizing L-ascorbic acid-2-glucoside - Google Patents
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- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
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- 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
- C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
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Abstract
The invention belongs to the technical field of biochemical synthesis, and particularly discloses methods for synthesizing L-ascorbic acid-2-glucoside, wherein 5, 6-O-isopropylidene-L-ascorbic acid is used as a starting material, 5, 6-O-isopropylidene-L-ascorbic acid-2-glucoside is prepared by reaction, reaction liquid obtained by the reaction is separated by using strong acid cation exchange resin, 5, 6-O-isopropylidene-L-ascorbic acid-2-glucoside can be hydrolyzed into L-ascorbic acid-2-glucoside, crystallization and drying are carried out, so that an L-ascorbic acid-2-glucoside product is obtained, and residual feed liquid after crystallization is recycled.
Description
Technical Field
The invention relates to the technical field of biochemical synthesis, in particular to methods for synthesizing L-ascorbic acid-2-glucoside.
Background
The structural formula of the L-ascorbic acid-2-glucoside (namely 2-O- α -D-glucopyranosyl-L-ascorbic acid) is shown in a formula (I), the L-ascorbic acid-2-glucoside is used as an important derivative of the L-ascorbic acid, is which is a whitening additive published and approved by the health administration, is a commonly recognized stable L-ascorbic acid derivative, is the most commonly used whitening component in various current brand cosmetic products, has good whitening effect, is chemically stable and has no stimulation to skin, so the L-ascorbic acid-2-glucoside is widely used by in cosmetic production at home and abroad, the L-ascorbic acid-2-glucoside entering human body cells is hydrolyzed by α -glucosidase to generate ascorbic acid and glucose, and the L-ascorbic acid-2-glucoside has the same reducing property as ascorbic acid and oxidation resistance, and the L-ascorbic acid-2-glucoside can continuously decompose in vivo to provide the ascorbic acid.
The patent document with application number 201010571709.9 discloses a manufacturing method of anhydrous crystal powder containing 2-O- α -D-glucosyl-L-ascorbic acid, a solution containing starch and L-ascorbic acid is subjected to sequential action of cyclodextrin glucanotransferase and glucoamylase to obtain a solution with 2-O- α -D-glucosyl-L-ascorbic acid productivity of 35% or more, the patent application with application number 201610985353.0 also discloses methods for preparing L-ascorbic acid-2-glucoside, sucrose phosphorylase produced by fermentation of an engineered strain of Escherichia coli using recombinant sucrose phosphorylase as a biocatalyst, sucrose as a glycosyl donor, L-ascorbic acid as a glycosyl acceptor, the preparation of L-ascorbic acid-2-glucoside products by biocatalysis is carried out by using sucrose phosphorylase as a glycosyl acceptor, the reaction of L-ascorbic acid-2-glucoside donor is carried out under the same conditions as L-glucopyranosyl-2-glycosyl transferase, L-ascorbic acid-2-glucopyranoside production reaction of L-ascorbic acid-2-glucose-glycosyl transferase is carried out by using L-ascorbic acid-glucopyranosyl-2-glucopyranoside-glycosyl transferase as a glycosyl donor, L-ascorbic acid donor, L-ascorbic acid is produced by-glucopyranosyl-glucopyranose, L-glucopyranosyl-2-glucopyranoside, L-glucopyranosyl-2-glucopyranoside is produced, L-glucopyranosyl-glucopyranoside production is produced, L-glucopyranosyl-L-glucopyranoside production is produced, L-2-glucopyranoside production is produced, L-glucopyranosyl-glucopyranose-glucopyranosyl-glucopyranose, L-glucopyranosyl-L-glucopyranosyl-L-glucopyranoside production is produced, L-glucopyranosyl-L-glucopyranoside production is produced, L-glucopyranosyl-L-.
The invention aims to find novel reaction substrates as starting materials for synthesizing L-ascorbic acid-2-glucoside so as to reduce the generation of byproducts.
Disclosure of Invention
The invention mainly solves the technical problem of providing a synthesis method of L-ascorbic acid-2-glucoside, which has simple separation and purification and high purity and yield of L-ascorbic acid-2-glucoside products.
In order to solve the technical problems, the invention adopts technical proposals that methods for synthesizing L-ascorbic acid-2-glucoside comprise the following steps:
(1) taking 5, 6-O-isopropylidene-L-ascorbic acid as a reaction raw material, adding a glucose group donor, and carrying out a biotransformation reaction under the action of glycosyltransferase;
(2) adding glucoamylase into the reaction liquid obtained after the reaction in the step (1) for hydrolysis reaction to prepare 5, 6-O-isopropylidene-L-ascorbic acid-2-glucoside;
(3) and (3) separating the reaction liquid containing the 5, 6-O-isopropylidene-L-ascorbic acid-2-glucoside obtained in the step (2) by adopting a strong acid cation exchange resin, crystallizing the separation liquid to separate out an L-ascorbic acid-2-glucoside product, and returning the residual feed liquid after the product is separated out to the step (1) for recycling. The reactions in the step (1) and the step (2) are carried out under the conditions of light and oxygen avoidance.
Preferably, the dosage of the glucose-based donor is 50-60% of the mass of the 5, 6-O-isopropylidene-L-ascorbic acid; and/or, the glycosyltransferase is used in an amount of: adding 650-700U glycosyltransferase per gram of the 5, 6-O-isopropylidene-L-ascorbic acid; and/or the dosage of the glucoamylase is as follows: 11500-12000U of glucoamylase is added per gram of the 5, 6-O-isopropylidene-L-ascorbic acid.
Preferably, an antioxidant is also added during the reaction in the step (1), and the using amount of the antioxidant is preferably 6-10% of the mass of the 5, 6-O-isopropylidene-L-ascorbic acid.
, preferably, the antioxidant is cysteine.
preferred embodiments are that the 5, 6-O-isopropylidene-L-ascorbic acid is prepared by reacting L-ascorbic acid with acetone, preferably, the L-ascorbic acid and the acetone are fed according to the proportion of the L-ascorbic acid to the acetone which is 1g (5 ml-10 ml), and the 5, 6-O-isopropylidene-L-ascorbic acid is prepared by catalytic reaction by using any or more of acetyl chloride, phosphorus oxychloride and stannous chloride as catalysts, wherein preferably adopts acetyl chloride, the proportion of the L-ascorbic acid to the acetone which is 1g (6 ml-8 ml) is preferably VC, and the reaction is carried out in a water bath at 20-50 ℃, preferably at 30-40 ℃, for 2-5 h, preferably for 4-5 h.
Preferably, the glucose group donor is any or more of β -cyclodextrin, gelatinized starch, soluble starch and maltodextrin.
Preferably, the glycosyl transferase is any or more of α -glucosidase, cyclodextrin glucoside transferase and α -amylase.
More preferably, the glucose-based donor is β -cyclodextrin.
Preferably, the glucoamylase is α -1, 4-glucohydrolase.
Preferably, the strong-acid cation exchange resin is a sulfonic acid group cation exchange resin with a styrene-divinyl copolymer as a matrix.
When the residual feed liquid after the product is separated out is returned to the step (1) for recycling, because the feed liquid still contains reaction materials, such as glucose-based donor, glycosyl transferase, glucoamylase and 5, 6-O-isopropylidene-L-ascorbic acid raw materials, the addition of the glucose-based donor, glycosyl transferase, glucoamylase and the like can be reduced or even avoided according to the actual composition of the residual feed liquid.
The invention provides a synthesis method of L-ascorbic acid-2-glucoside, which comprises the following steps of firstly reacting 5, 6-O-isopropylidene-L-ascorbic acid to prepare 5, 6-O-isopropylidene-L-ascorbic acid-2-glucoside, separating reaction liquid obtained by the reaction by using strong acid cation exchange resin, hydrolyzing the 5, 6-O-isopropylidene-L-ascorbic acid-2-glucoside into L-ascorbic acid-2-glucoside, crystallizing and drying to obtain an L-ascorbic acid-2-glucoside product, and recycling residual liquid after crystallization.
The method adopts 5, 6-O-isopropylidene-L-ascorbic acid as a reaction raw material, and 5-hydroxy and 6-hydroxy of the raw material are protected by forming isopropylidene, so that the reaction activity is reduced, the 2-hydroxy is mainly used for reaction, the generation of 5-O- α -D-glucopyranosyl-L-ascorbic acid and 6-O- α -D-glucopyranosyl-L-ascorbic acid by-products is avoided, the subsequent separation and purification difficulty is reduced, the purity and yield of the L-ascorbic acid-2-glucoside product are improved, and the crystallization yield is also improved.
Detailed Description
The technical solution of the present invention will be explained in detail below.
Example 1
Adding 25g of L-ascorbic acid and 150ml of acetone into a 250ml dry three-neck round-bottom flask with a stirring thermometer, placing the reaction system in a water bath at 30 ℃, starting stirring, adding 2ml of acetyl chloride under strong stirring, reacting for 2h, adding 2ml of acetyl chloride again, continuing reacting for 2h, performing suction filtration, and drying under reduced pressure to obtain a white acicular solid, namely a 5, 6-O-isopropylidene-L-ascorbic acid product with the molecular weight of 216.19 and the testing melting point of 217 ℃ (dec.).
Putting 5g of β -cyclodextrin into 65ml of 86 g/L5, 6-O-isopropylidene-L-ascorbic acid aqueous solution, then adding 0.70g of cysteine, then preserving heat in 37 ℃ water bath for 10min, then adjusting the pH of the feed liquid to 5-6, adding 10ml (600U/ml) of cyclodextrin glucoside transferase, putting the reaction system in a shaking table, preserving heat and reacting for 24h under the condition of avoiding light and oxygen, keeping the pH at about 5.5, then heating the feed liquid to 42 ℃, adding 1ml of α -1, 4-glucose hydrolase (10 ten thousand U/ml), continuing the reaction for 3 h, after the reaction is finished, separating the obtained reaction feed liquid through strong acid cation exchange resin, wherein the strong acid cation exchange resin is sulfonic cation exchange resin taking a styrene-divinyl copolymer as a matrix, the obtained separation liquid contains L-ascorbic acid-2-glucoside, 5.71g of pure ascorbic acid-2-glucoside, crystallizing and drying, and actually obtaining L-ascorbic acid-2-divinyl copolymer powder, wherein the mass percent of the L-ascorbic acid glucoside is tested as the main crystal yield, and the mass percent of the cyclodextrin is that the L-ascorbic acid glucoside 5.8-2-90% of the cyclodextrin and the cyclodextrin, and the HPLC cyclodextrin is tested as the melting point of the cyclodextrin.
A small amount of antioxidant such as cysteine is added into the reaction system, so that unreacted 5, 6-O-isopropylidene-L-ascorbic acid can be protected in the glycosyl transfer reaction process and after the reaction is finished, the utilization rate of the 5, 6-O-isopropylidene-L-ascorbic acid raw material is improved, the cost is reduced, and the product quality is improved.
If the L-ascorbic acid is used as a starting material, 5, 6-O-isopropylidene-L-ascorbic acid is prepared firstly, then the L-ascorbic acid-2-glucoside is prepared by adopting the method, and similarly, a small amount of antioxidant is added into the reaction liquid, so that the oxidation of the L-ascorbic acid can be delayed, the oxidative discoloration of the L-ascorbic acid can be prevented, the loss of the L-ascorbic acid in the reaction process can be reduced, and the utilization rate of the L-ascorbic acid can be further improved by .
Example 2
In this example, the crystallized feed liquid obtained in example 1 was used, β -cyclodextrin (4 g) and 5, 6-O-isopropylidene-L-ascorbic acid (4.34 g) were added to the crystallized feed liquid obtained in example 1, 0.70g of cysteine was added, the mixture was kept in a water bath at 37 ℃ for 10min, the pH of the feed liquid was adjusted to 5-6, 8ml (600U/ml) of cyclodextrin glucoside transferase was added, the reaction system was placed in a shaker under dark and oxygen-free conditions, the pH was kept at about 5.5 after 24h of reaction at 37 ℃, the feed liquid was then heated to 42 ℃, 1ml of α -1, 4-glucosyl hydrolase (10 ten thousand U/ml) was added, the reaction was continued for 3 hours, the reaction was completed, the feed liquid obtained by the reaction was subjected to cation exchange resin separation, the cation exchange resin was styrene-divinyl copolymer-based cation exchange resin, the L-ascorbic acid-2-glucoside pure-61 g, 5.187 g, crystal pure L-ascorbic acid crystal was dried, the crystal yield was determined by HPLC, and the percentage of the crystal was found to be 2.187-90% by HPLC using strong acid glucoside, the HPLC, the strong acid crystal yield was found to be 2.5.5.5-90%.
Example 3
In this example, the crystallized feed solution obtained in example 2 was used, 3g of β -cyclodextrin and 3.35g of 5, 6-O-isopropylidene-L-ascorbic acid were added to the crystallized feed solution obtained in example 2, 0.70g of cysteine was added, the mixture was kept in a water bath at 37 ℃ for 10min, the pH of the feed solution was adjusted to 5 to 6, 6ml (600U/ml) of cyclodextrin glucoside transferase was added, the reaction system was placed in a shaker under conditions of light and oxygen exclusion, the pH was kept at about 5.5 after keeping the reaction for 24h at 37 ℃, then the reaction was continued for 3 h by heating the feed solution to 42 ℃ and adding 1ml of α -1, 4-glucohydrolase (10 ten thousand U/ml), the reaction was carried out, the feed solution obtained by the reaction was separated by a cation exchange resin based on styrene-divinyl copolymer, the L-ascorbic acid pure 2-glucoside was isolated by 5.50g, the crystal was dried to a crystalline yield of 0.01-5.187% L-5 g of ascorbic acid, and the percentage of L-5.01-90% ascorbic acid was determined by HPLC.
In example 3, the residual ascorbic acid in the feed liquid after crystallization is 1.71g, and the total utilization rate of the ascorbic acid in examples 1 to 3 is 80.9%.
It can be seen from the above examples that, in examples 2 and 3 of the present invention, the crystallized feed liquid is recycled, so that the obtained L-ascorbic acid-2-glucoside product has stable quality, the content of L-ascorbic acid-2-glucoside in the L-ascorbic acid-2-glucoside product is not less than 99%, the crystallization yield is greater than 90%, and the total utilization rate of ascorbic acid is greater than 80%.
Claims (10)
1, methods for synthesizing L-ascorbic acid-2-glucoside, comprising the steps of:
(1) taking 5, 6-O-isopropylidene-L-ascorbic acid as a reaction raw material, adding a glucose group donor, and carrying out a biotransformation reaction under the action of glycosyltransferase;
(2) adding glucoamylase into the reaction liquid obtained after the reaction in the step (1) for hydrolysis reaction to prepare 5, 6-O-isopropylidene-L-ascorbic acid-2-glucoside;
(3) and (3) separating the reaction liquid containing the 5, 6-O-isopropylidene-L-ascorbic acid-2-glucoside obtained in the step (2) by adopting a strong acid cation exchange resin, crystallizing the separation liquid to separate out an L-ascorbic acid-2-glucoside product, and returning the residual feed liquid after the product is separated out to the step (1) for recycling.
2. The method for synthesizing L-ascorbic acid-2-glucoside according to claim 1, wherein the amount of the glucose-based donor is 50 to 60% of the mass of the 5, 6-O-isopropylidene-L-ascorbic acid; and/or, the glycosyltransferase is used in an amount of: adding 650-700U glycosyltransferase per gram of the 5, 6-O-isopropylidene-L-ascorbic acid; and/or the dosage of the glucoamylase is as follows: 11500-12000U of glucoamylase is added per gram of the 5, 6-O-isopropylidene-L-ascorbic acid.
3. The method for synthesizing L-ascorbic acid-2-glucoside according to claim 1, wherein an antioxidant is further added during the reaction in step (1), and the amount of the antioxidant is preferably 6-10% of the mass of 5, 6-O-isopropylidene-L-ascorbic acid.
4. The method for synthesizing L-ascorbic acid-2-glucoside of claim 3, wherein the antioxidant is cysteine.
5. The method of synthesizing L-ascorbic acid-2-glucoside of claim 1, wherein the 5, 6-O-isopropylidene-L-ascorbic acid is prepared by reacting L-ascorbic acid with acetone;
the 5, 6-O-isopropylidene-L-ascorbic acid is preferably prepared by the following method that L-ascorbic acid and acetone are fed according to the proportion of L-ascorbic acid to acetone which is 1g (5 ml-10 ml), and any or more of acetyl chloride, phosphorus oxychloride and stannous chloride are adopted as catalysts to catalyze and react to prepare the 5, 6-O-isopropylidene-L-ascorbic acid.
6. The method for synthesizing L-ascorbic acid-2-glucoside of claim 1, wherein said glucose group donor is any of β -cyclodextrin, gelatinized starch, soluble starch, maltodextrin or more .
7. The method for synthesizing L-ascorbic acid-2-glucoside of claim 6, wherein said glycosyltransferase is any or several of α -glucosidase, cyclodextrin glucoside transferase, α -amylase.
8. The method of synthesizing L-ascorbic acid-2-glucoside of claim 1, wherein said glucose-based donor is β -cyclodextrin and said glycosyltransferase is cyclodextrin glucoside transferase.
9. The method for synthesizing L-ascorbic acid-2-glucoside of any of claims 1 or 6 to 8 of , wherein the glucoamylase is α -1, 4-glucohydrolase.
10. The method for synthesizing L-ascorbic acid-2-glucoside according to claim 1, wherein said strongly acidic cation exchange resin is a sulfonic acid group cation exchange resin having a styrene-divinyl copolymer as a matrix.
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Cited By (3)
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| CN112592374A (en) * | 2020-12-03 | 2021-04-02 | 安徽泰格生物技术股份有限公司 | Preparation method of 6-O-palmitoyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acid |
| CN115651035A (en) * | 2022-10-29 | 2023-01-31 | 重庆东寰科技开发有限公司 | Method for chemically synthesizing L-ascorbic acid-2-glucoside AA-2G |
| CN115976157A (en) * | 2022-12-30 | 2023-04-18 | 黑龙江新和成生物科技有限公司 | High-throughput screening method of cyclodextrin transferase for catalytic synthesis of L-ascorbic acid-2-glucoside |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112592374A (en) * | 2020-12-03 | 2021-04-02 | 安徽泰格生物技术股份有限公司 | Preparation method of 6-O-palmitoyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acid |
| CN115651035A (en) * | 2022-10-29 | 2023-01-31 | 重庆东寰科技开发有限公司 | Method for chemically synthesizing L-ascorbic acid-2-glucoside AA-2G |
| CN115651035B (en) * | 2022-10-29 | 2024-06-28 | 重庆东寰科技开发有限公司 | Method for chemically synthesizing L-ascorbic acid-2-glucoside AA-2G |
| CN115976157A (en) * | 2022-12-30 | 2023-04-18 | 黑龙江新和成生物科技有限公司 | High-throughput screening method of cyclodextrin transferase for catalytic synthesis of L-ascorbic acid-2-glucoside |
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