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Alpha-hydroxy acid deracemisation method and strain

The technology of hydroxy acid and hydroxy acid dehydrogenase is applied in the field of double bacteria coupling catalysis of racemic α-hydroxy acid to produce chiral α-hydroxy acid, which can solve the problems of high cost, small processing capacity, high price and the like, To achieve the effect of less environmental pollution, mild reaction conditions, and reduction of extraction steps

Active Publication Date: 2012-09-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, the preparation of optically active mandelic acid and its derivatives mainly adopts the chemical resolution method of the racemate: first synthesize the racemate of mandelic acid, and then use a certain method to resolve it. The method of resolution is mainly There are the following types: ①Diastereomeric salt crystallization resolution method, the common problem faced is that it is expensive and has certain toxicity, which causes waste of resources and environmental pollution to a certain extent. At present, the large-scale production of R in my country -Mandelic acid is produced by this method
② Chromatographic separation method, the equipment cost of this method is too high, the consumption is large, the cost is too high, and the processing capacity is small, so it is limited to detection and laboratory preparation, and cannot be used for commercial production
④The capillary electrophoresis separation method is widely used in the separation of various drug enantiomers due to its high efficiency, rapidity, and economy. This method has disadvantages such as high cost

Method used

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  • Alpha-hydroxy acid deracemisation method and strain
  • Alpha-hydroxy acid deracemisation method and strain
  • Alpha-hydroxy acid deracemisation method and strain

Examples

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Embodiment 1

[0035] Embodiment 1: the fermentation culture of Pseudomonas aeruginosa CCTCC M 2011394

[0036] Fermentation medium: mannitol 10g / L, yeast extract powder 10g / L, K 2 HPO 4 2.5g / L, KH 2 PO 4 2.5g / L, CuCl 2 0.01g / L, NaCl 1g / L, inducer o-chloromandelic acid 2.5g / L, prepared with tap water, pH 7.0, sterilized at 121°C for 20min. After sterilization, cool down and inoculate. Fill a 250mL Erlenmeyer shaker flask with 20% liquid, inoculate a ring of Pseudomonas aeruginosa CCTCC M 2011394, culture at 30°C and 150rpm for 48 hours, centrifuge the fermentation broth and wash twice with normal saline, and collect wet cells after centrifugation ,spare.

Embodiment 2

[0037] Embodiment 2: the fermentation culture of Sinorhizobium CCTCC No: M 2011391

[0038] Fermentation medium: glucose 10g / L, yeast extract 10g / L, K 2 HPO 4 2.5g / L, KH 2 PO 4 2.5g / L, MgSO 4 0.2g / L, FeSO 4 0.03g / L, NaCl 1g / L, inducer mandelic acid 2g / L, prepared in tap water, pH 7.0, sterilized at 121°C for 20min. After sterilization, cool down and inoculate. In a 250mL Erlenmeyer shaker flask with 20% liquid, inoculate a ring of Sinorhizobium CCTCC No: M 2011391, culture at 30°C, 150rpm for 48 hours, centrifuge the fermentation broth and wash twice with normal saline, and collect the wet cells after centrifugation ,spare.

Embodiment 3

[0039] Example 3: Fermentation of Saccharomyces cerevisiae CCTCC No: M 2011393

[0040] Fermentation medium: glucose 20g / L, yeast extract 15g / L, K2HPO4 2.5g / L, KH2PO4 2.5g / L, MgSO 4 0.2g / L, FeSO4 0.03g / L, NaCl 1g / L, prepared with tap water, adjusted pH to 7.0. 250mL Erlenmeyer shaker flask with 20% liquid volume, inoculated with a ring of Saccharomyces cerevisiae CCTCC No: M 2011393, 30°C, 150rpm culture Two days later, the fermented broth was centrifuged and washed twice with physiological saline after the culture was completed, and the wet bacterial cells were collected after centrifugation for future use.

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Abstract

The invention provides a method for preparing chiral alpha-hydroxy acid by double bacterium coupled catalysis of racemic alpha-hydroxy acid, comprising the following steps: using an alpha-hydroxy acid raceme of formula (I) as a substrate and using (S)-alpha-hydroxy acid dehydrogenase and (R)-keto acid reductase as a catalyst, reacting in a buffer with the pH value of 6.0-9.0 at 20-50 DEG C for 10-48 h to prepare the corresponding (R)-alpha-hydroxy acid. According to the invention, the chiral alpha-hydroxy acid is synthesized by using the racemic alpha-hydroxy acid as the substrate and carrying out deracemization through biotransformation, thus the reaction conditions are mild, the environmental pollution is low, the extraction step of intermediates is omitted, and the yield and enantiomerexcess are high, wherein the yield reaches more than 90% and the enantiomer excess reaches more than 99%.

Description

(1) Technical field [0001] The invention relates to a method for producing chiral α-hydroxy acid by catalyzing racemic α-hydroxy acid through double bacteria coupling, and a new bacterial strain used in the process. (2) Background technology [0002] Optically active α-hydroxy acids refer to a class of compounds with hydroxyl and carboxyl groups on the chiral carbon. They are important chiral "building blocks" and can be used for the asymmetric synthesis of a large number of bioactive molecules. Among these compounds, optically pure mandelic acid is considered to be the most important representative from a commercial point of view. Mandelic acid is also known as a-hydroxyphenylacetic acid, mandelic acid, and mandelic acid. The structural formulas of its R-type and S-type are as follows: [0003] [0004] Optically active mandelic acid and its derivatives are extremely important pharmaceutical intermediates: such as R-(-)-mandelic acid is widely used in the synthesis of v...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P39/00C12P7/42C12N1/18C12R1/385C12R1/41C12R1/865
Inventor 郑裕国薛亚平张雅琴沈寅初
Owner ZHEJIANG UNIV OF TECH
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