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Immobile bacillus and method for resolving and preparing chiral cyclopentenylone using said bacillus

A cyclopentenone, bacillus technology, applied in the direction of bacteria, fermentation, etc., can solve the problems of low activity and selectivity of bacteria and high price

Inactive Publication Date: 2003-04-09
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The second technical problem to be solved in the present invention is to disclose the method for preparing chiral cyclopentenone by catalytic resolution of the strains, so as to overcome the high price of commercial enzyme preparations in the prior art, or the low activity of the strains used. less selective defect

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] 150 mL of growth medium (containing 1% sucrose, 0.15% Tween-80, 2% soybean cake powder, 0.2% ammonium sulfate, K 2 HPO 4 0.2%, NaCl 0.1%, MgSO 4 0.02%, pH8.0), after sterilization, insert the YQ231 seed culture solution according to the inoculum size of 6%, and cultivate it on a shaker at a temperature of 30°C and 140r / min for 24h.

[0045] Take 100mL of the above-mentioned culture solution, collect the bacteria by centrifugation, wash with normal saline, suspend in 100mL barbital sodium-hydrochloric acid buffer (100mM, pH8.5), add 1.5g nonylphenol polyoxyethylene ether, and then add Concentration is the allyl alcohol ketone acetate of 5wt%, on the shaker insulation reaction of 30 ℃ and 160r / min, generate (R)-allyl alcohol ketone, the result is: when the reaction is carried out to 2 hours, the conversion rate is higher than 30%, continue to react to 14 hours, the reaction is close to the end point (50%), at this moment, ee S and ee P Up to 80%, the enantioselectivi...

Embodiment 2

[0047] Take 50 mL of the fermentation broth in Example 1, collect the bacteria by centrifugation, wash with physiological saline, suspend in 100 mL of barbiturate sodium-hydrochloric acid buffer (100 mM, pH8.5), add 1.5 g of nonylphenol polyoxyethylene Ether, then add 2.0g of allyl alcohol ketone acetate, and keep it warm on a shaking table at 30°C and 160r / min. S and ee P At 90%, the E value is close to 50.

Embodiment 3

[0049] 3L of growth medium (containing 1% sucrose, 0.15% Tween-80, 2% soybean cake powder, 0.2% ammonium sulfate, K 2 HPO 4 0.2%, NaCl 0.1%, MgSO 4 0.02%, pH8.0), after sterilization, insert the YQ231 seed culture solution according to the inoculation amount of 5%, and ferment under the conditions that the temperature is 30°C, the stirring speed is 500r / min and the ventilation rate is 1.0vvm, and the The bacterial concentration in the tank is 3g / L (dry weight), and the enzyme activity is 900U / L.

[0050]Take 50 mL of the above fermentation broth, dilute it to 100 mL with 0.1 M, pH 8.0 potassium phosphate buffer solution, directly add 2 g of allyl alcohol ketone acetate and 1.5 g of nonylphenol polyoxyethylene ether, stir magnetically at 30 ° C for 3 h, stop Reaction and extraction with ethyl acetate, after distilling off the solvent, (R)-allyl ketone and (S)-allyl ketone acetate with enantiomeric purity exceeding 94% are obtained; add 3g of acetone again, at a temperature ...

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PUM

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Abstract

The present invention discloses a kind of immobile bacillus CGMCC0789 and the preparation process of chiral cyclopentenylone with the bacillus. During the preparation, microbe cell with esterase activity or its separated esterase is used as catalyst and fatty ester racemic alcohol ketone is used as material to produce conversion reaction to obtain the mixture of (R)-alcohol ketone fatty ester and(S)-alcohol ketone fatty ester. The mixture is then made to produce sulfonylation and alkali hydrolysis and the final product single (S)-alcohol ketone natipode is collected from the hydrolysate. Thepresent invention has simple technological process, mid reaction condition, bacteria strain with high catalytic activity and stereo selectivity, and the product (S)-alcohol ketone has optical purity over 90%.

Description

technical field [0001] The invention belongs to the field of biochemical engineering, and relates to an Acinetobacter and a method for preparing enantiomers of chiral compounds by using the microorganism to catalyze the resolution, in particular to a method for preparing cyclopentenone-type chiral alcohol enantiomers by resolution . Background technique [0002] The cyclopentenone-type chiral alcohol compound is an important intermediate for producing pyrethroid insecticides. The basic skeleton of the cyclopentenone-type alcohol compound involved in the present invention is: 4-hydroxyl-3-methyl- Cyclopent-2-en-1-one mainly includes two varieties, the chemical structural formula is as follows: [0003] Wherein: formula (I) is 2-allyl-3-methyl-4-hydroxycyclopent-2-en-1-one, hereinafter referred to as allyl alcohol ketone; formula (II) is 2-propargyl- 3-methyl-4-hydroxycyclopent-2-en-1-one, hereinafter referred to as propargyl alcohol ketone; the two can be collectively ref...

Claims

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Application Information

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IPC IPC(8): C12N1/20C12P7/26C12P41/00
Inventor 许建和赵玉巧武慧渊陈亚周琳婷
Owner EAST CHINA UNIV OF SCI & TECH
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