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Microorganism catalysis prepared (2S,3R)-2-benzoyl aminomethyl-3-hydroxybutyric acid ester and bacterial strain

A technology of benzoylaminomethyl and hydroxybutyrate, which is applied in the field of microbial catalytic preparation of (2S, 3R)-2-benzoylaminomethyl-3-hydroxybutyrate and strains, and can solve the problem of 2- Benzoylaminomethyl-3-hydroxybutyrate has problems such as few reports, low recovery rate, and complicated operation, which achieves good industrial application prospects, mild reaction conditions, and simple operation procedures.

Active Publication Date: 2014-06-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Since in the above-mentioned reported methods, the main configurations of the products obtained by the asymmetric reduction of baker’s yeast carbonyl group are all (2S, 3S) configuration products, it is necessary to go through the steps of configuration reversal by chemical methods, the operation is cumbersome, and the recovery rate is very low. Low
[0010] However, there are few reports on the direct catalytic preparation of (2S, 3R)-2-benzamidomethyl-3-hydroxybutyrate by microbial cells

Method used

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  • Microorganism catalysis prepared (2S,3R)-2-benzoyl aminomethyl-3-hydroxybutyric acid ester and bacterial strain
  • Microorganism catalysis prepared (2S,3R)-2-benzoyl aminomethyl-3-hydroxybutyric acid ester and bacterial strain
  • Microorganism catalysis prepared (2S,3R)-2-benzoyl aminomethyl-3-hydroxybutyric acid ester and bacterial strain

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: Screening, identification of microorganisms

[0042] (1) Screening of microorganisms

[0043] Strain enrichment medium: glucose 20g / L, yeast extract 10g / L, peptone 20g / L, 2-benzamidomethyl-3-oxobutyric acid methyl ester 40g / L, dimethyl sulfoxide 40mL / L, the solvent is water, pH 7.0.

[0044] Plate medium and slant medium: glucose 20g / L, yeast extract 10g / L, peptone 20g / L, agar 20g / L, solvent is water, pH 7.0.

[0045] Seed solution medium: glucose 20g / L, yeast extract 10g / L, peptone 20g / L, solvent is water, pH 7.0.

[0046] Fermentation enzyme production medium: glucose 30g / L, yeast extract 30g / L, NaCl 4g / L, solvent is water, pH 7.0.

[0047] More than 200 soil samples were collected from vegetable orchard plant clusters in Zhejiang, Guangdong, Shandong, Liaoning and Jiangsu for strain screening. The specific process is as follows:

[0048] Take a little soil sample and add it to physiological saline to make a soil suspension, which is enriched twice...

Embodiment 2

[0062] Example 2: Preparation of wet thallus of Burkholderia gladiolus ZJB-12126

[0063] (1) Slant culture: Burkholderia gladioli ZJB-12126 was inoculated on the slant medium and cultured at 30°C for 24 hours to obtain slant cells. The formula of the slant medium is: glucose 20g / L, yeast extract 10g / L, peptone 20g / L, agar 20g / L, the solvent is water, and the pH is 7.0.

[0064] (2) Seed cultivation: pick a ring of bacteria from the slant with an inoculation loop and inoculate it in the seed medium, and cultivate it at 30°C and 150r / min for 16 hours to obtain the seed liquid. The formula of the seed medium is: glucose 20g / L, yeast extract 10g / L, peptone 20g / L, the solvent is water, and the initial pH is 7.0.

[0065] (3) Fermentation culture: Inoculate the cultured seed liquid into the fermentation medium at a volume ratio of 2% to obtain bacteria. The formula of the fermentation medium is: glucose 20g / L, yeast extract 10g / L, NaCl 2g / L, the solvent is water, the initial pH i...

Embodiment 3

[0066] Example 3: Preparation of wet thallus of Burkholderia gladiolus ZJB-12126

[0067] (1) Incline cultivation: same as in Example 2.

[0068] (2) Seed culture: same as Example 2.

[0069] (3) Fermentation culture: Inoculate the cultured seed liquid into the fermentation medium at a volume ratio of 5% to obtain bacteria. The formula of the fermentation medium is: glucose 30g / L, yeast extract 30g / L, NaCl 5g / L, the solvent is water, the initial pH is 7.0, cultivated at 30°C and the shaker rotation speed 150r / min for 24 hours to obtain Fermentation broth containing bacterial cells. The fermentation broth was centrifuged, and the supernatant was discarded. After the precipitate was washed twice with physiological saline, the precipitate was collected by centrifugation to obtain wet thallus. The yield of the wet thallus was 83 g / L.

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Abstract

The invention provides Burkholderia gladioli ZIB-12126, which is a new bacterial strain capable of catalyzing asymmetrical reduction of carbonyl, and application of the bacterial strain in preparation of (2S,3R)-2-benzoyl aminomethyl-3-hydroxybutyric acid ester by racemizing 2-benzoyl aminomethyl-3-hydroxybutyric acid ester in a microbial conversion mode. The bacterial strain is preserved in the Chinese Typical Culture Collection Center with an address of Wuhan College, Wuhan, China and the zip code of 430072, the preservation serial number of CCTCC No. M 2012379 on September 255th, 2012. The bacterial strain provided by the invention is used for synthesizing the (2S,3R)-2-benzoyl aminomethyl-3-hydroxybutyric acid ester through biologic conversion, with gentle reaction condition and environmental-friendliness; and more importantly, the product configuration is mainly (2S,3R) configuration, and step of turning the product configuration by using a chemical method is not needed, so that the operation process is simple and has good industrial application prospects.

Description

(1) Technical field [0001] The present invention relates to Burkholderia gladioli (Burkholderia gladioli) ZJB-12126, and its preparation formula (I) (2S , 3R)-2-benzamidomethyl-3-hydroxybutyrate application. (2) Background technology [0002] 4-Acetoxyazetidinone (abbreviated as 4AA), is an important chiral synthon and an important intermediate for the synthesis of new broad-spectrum antibiotics of carbapenems and penems, such as for the synthesis of Imipenem, faropenem, meropenem, etc. [0003] The chemical structural formula of 4AA is shown in formula (I). The molecular skeleton of 4AA is characterized by a quaternary lactam ring, which contains 3 chiral centers and 8 stereoisomers. How to establish chiral centers with high selectivity is the key to the synthesis of 4AA. Japan's Noyori and Takasago companies adopt the route with ethyl acetoacetate as the starting material, the yield and stereoselectivity of each step are all good, and the total yield is as high as 50%, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12N1/20C12P41/00C12P13/02C12R1/01
Inventor 郑裕国孙丽慧陈翔张国海沈寅初
Owner ZHEJIANG UNIV OF TECH
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