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Ayerbodotella wzz10 and its application in the chiral resolution of 2-tetrahydrofuroic acid

A technology of bacillus and ethyl tetrahydrofuroate, which is applied in the field of application of ethyl-2-tetrahydrofuroate and -2-tetrahydrofuroic acid, can solve the problem that the yield and high optical purity cannot be satisfied at the same time, and the reaction Long time and other problems, to achieve the effect of high yield, strong stereoselectivity and simple separation

Active Publication Date: 2022-04-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally speaking, the biggest problem of enzymatic separation is that the yield and high optical purity cannot be satisfied at the same time, and the reaction time is long

Method used

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  • Ayerbodotella wzz10 and its application in the chiral resolution of 2-tetrahydrofuroic acid
  • Ayerbodotella wzz10 and its application in the chiral resolution of 2-tetrahydrofuroic acid
  • Ayerbodotella wzz10 and its application in the chiral resolution of 2-tetrahydrofuroic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Isolation, purification and identification of embodiment 1 bacterial strain WZZ10

[0026] 1. Isolation and purification of enantioselective strains

[0027] (1) Enrichment: Collect soil samples polluted by heavy oil pollution from all over Hangzhou for enrichment and culture. Take 1 g of soil, add it into a shaker flask containing 50 mL of sterile water and a small amount of glass beads, and incubate with shaking at 30 °C and 180 rpm for 5 h. Take 1mL of the suspension and serially dilute to 10 -6 , take 200 μL and spread it on LB solid medium, and incubate at 30°C for 24h.

[0028] LB solid medium formula: peptone 10g / L, yeast powder 5g / L, NaCl 10g / L, dissolved in water, adjusted to pH 7.0, sterilized at 115°C for 30min.

[0029] (2) Primary screening (screening of lipase-producing bacteria):

[0030] Pick a single colony and inoculate it on a rhodamine B color developing plate, and incubate at 30°C for 72h. According to the order of the color change circle, the ...

Embodiment 2

[0067] Embodiment 2: the application of bacterial strain WZZ10

[0068] (1) Preparation of WZZ10 dry bacteria powder

[0069] Inoculate the Bacillus ayerbordella WZZ10 strain into the slant medium and culture it at 28°C for 1 day to obtain the slant bacteria; the composition of the slant medium: peptone 10g / L, yeast extract 5g / L, NaCl10g / L, mass concentration 2 % agar, the solvent is deionized water, the pH is 7.0;

[0070] Inoculate the slant of Bacillus ayerbacillus WZZ10 into 50 mL of seed culture medium, and cultivate it at 28°C and 180 r / min for 12 hours to obtain the seed liquid;

[0071] Take 1 mL of seed liquid and inoculate in 100 mL of fermentation medium, and culture at 28°C and 180 r / min for 24 hours to obtain fermentation liquid. Centrifuge the fermentation broth at 12000rpm for 3min, discard the supernatant, take the wet bacteria and freeze it at -20°C, and then freeze-dry it in a cold trap at -80°C and a vacuum of 20Pa with a vacuum freeze dryer for 12h to obt...

Embodiment 3

[0077] Get 1g of Bacillus ayerbordella WZZ10 dried bacteria powder prepared by the method of Example 2 and 1.5g of racemic (R, S) ethyl 2-tetrahydrofuroate to 100mL pH7.0 phosphate buffer, at 28 After reacting for 7.5h under the condition of ℃ and stirring speed of 180rpm, the ee value of (S)-2-tetrahydrofuroic acid ethyl ester was 94.52% using the detection method of Example 1, and the ee value of (R)-2-tetrahydrofuroic acid 74.31%, (R)-2-tetrahydrofuroic acid conversion rate 56.18%.

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Abstract

The invention discloses a kind of Bacillus ayerbordella WZZ10 and its application in the chiral resolution of 2-tetrahydrofuroic acid: the wet thallus or the wet thallus obtained by fermenting and culturing Bacillus ayerbordella WZZ10 Freeze-dried dry cells are used as catalyst, racemic (R,S)-tetrahydrofuroic acid is used as substrate, phosphate buffer solution with pH 7.0 is used as reaction medium, at 20-35°C, 150-200rpm The resolution was carried out to prepare ethyl (S)-2-tetrahydrofuroate and (R)-2-tetrahydrofuroic acid. The enzyme-producing microbial strain Bacillus aryabhattai WZZ10 provided by the invention has strong stereoselectivity, (S)-2-ethyl tetrahydrofuroate ee value (optical purity)≧96%, and conversion rate of 58%, avoiding the manual process in chemical production The use of additives, low energy consumption, short reaction time, less environmental pollution, has the potential of industrial production.

Description

(1) Technical field [0001] The present invention relates to the resolution of ethyl (R, S)-2-tetrahydrofuroate, in particular to Bacillus ayerbordella WZZ10 strain and the three-dimensional resolution of ethyl (R, S)-2-tetrahydrofuroate Application of obtaining optically pure ethyl (S)-2-tetrahydrofuroate and (R)-2-tetrahydrofuroic acid. (2) Background technology [0002] 2-Tetrahydrofuroic acid (2-Tetrahydrofuroic acid), whose chemical name is tetrahydrofuran-2-carboxylic acid, is an important chemical intermediate widely used in medicine, chemical industry and other fields. Optically pure 2-tetrahydrofuroic acid is an important raw material for asymmetric synthesis, in which (R)-tetrahydrofuran-2-carboxylic acid is a chiral intermediate for the synthesis of penem antibiotics, and (S)-tetrahydrofuran-2-carboxylic acid is a synthetic Chiral intermediates of oxazosin drugs, and their derivatives are widely used in the synthesis of drugs including diuretics, alfuzosin, flopen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12N1/20C12P41/00C12P17/04C07D307/24C12R1/07
CPCC12N1/20C12P41/001C12P41/005C12P17/04C07D307/24C12R2001/07C12N1/205
Inventor 章银军夏颖鄢洪德郑建永汪钊
Owner ZHEJIANG UNIV OF TECH