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A method for preparing (s)-phenylethylene glycol by asymmetric separation of microorganisms

A phenylethylene glycol, asymmetric technology, applied in the field of preparation of (S)-phenylethylene glycol by asymmetric separation of microorganisms, can solve the problems of low reaction yield, low substrate solubility, toxic effects, etc. Achieve the effect of improving enantiomeric purity and yield, increasing substrate concentration, and inhibiting product toxicity

Active Publication Date: 2020-07-28
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, biocatalysis often has problems such as low substrate solubility, poisonous effect of substrate products on microbial cells, and inhibitory effect of substrate products on catalytic reactions in traditional aqueous phase systems, which makes the reaction yield low and catalyst utilization Low rate, high production cost

Method used

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  • A method for preparing (s)-phenylethylene glycol by asymmetric separation of microorganisms
  • A method for preparing (s)-phenylethylene glycol by asymmetric separation of microorganisms
  • A method for preparing (s)-phenylethylene glycol by asymmetric separation of microorganisms

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 Bacterial Strain Cultivation

[0046] Prepare seed medium and fermentation medium according to the following formulas:

[0047] SC0312 seed medium: Take 0.15g of yeast extract, 0.25g of NaCl and 0.5g of tryptone, add it into distilled water to make 50mL of seed medium, and sterilize at 121°C for 20min.

[0048] SC0312 fermentation medium: Take 0.3g of yeast extract, 0.5g of NaCl and 1g of tryptone, add it into distilled water to make 100mL of fermentation medium, and sterilize at 121°C for 20min.

[0049] Take 1‰ (v / v) (50μL) of Kouterella gibsonii and add it to 50mL seed medium, shake and cultivate at 37°C and 180rpm for 10-12h to obtain the seed culture solution; then add 1‰ (v / v ) (100 μL) inoculum size, the seed culture solution was added to 100 mL of fermentation medium, cultured at 37° C. and 180 rpm for 12 to 16 hours, and the fermentation solution was harvested.

[0050] The fermentation broth was centrifuged at 4° C. and 7900 rpm for 10 min to colle...

Embodiment 2

[0051] The influence of embodiment 2 organic solvents on biocatalytic reaction

[0052] Add 2mL of 100mM, pH 6.5 phosphate buffer and 2mL of organic solvents (tert-amyl alcohol, n-hexanol, 2-methyltetrahydrofuran, dibutyl phthalate, dimethyl carbonate, butyl acetate, etc. ester, isooctane, n-decane, dipentene) to form a biphasic system with a volume ratio of 1:1, and then add 11.05 mg of racemic (R, S)-phenylethylene glycol (that is, the final concentration 20mM) and 0.10g of Gitkut bacteria (that is, the final concentration is 25mg / mL), reacted at 35°C and 180rpm for 6h, and after the reaction was completed, the product (S)-phenylben The enantiomeric excess of diol is respectively 0.05%, 0.03%, 0.04%, 99.99%, 0.02%, 0.54%, 0.71%, 99.99%, 0.03% (the product liquid phase chromatogram is as follows figure 1 and 2 shown).

Embodiment 3

[0053] The influence of embodiment 3 reaction initial pH on biocatalytic reaction

[0054] Add 2mL of 100mM to a 25mL serum bottle, then add phosphate buffer solution of different pH (pH is 4.5, 5, 5.5, 6.5, 7.5, 8.5) and 2mL of dibutyl phthalate to form a volume ratio of 1 : 1 biphasic system, then add 11.05mg of racemic (R, S)-phenylethylene glycol (final concentration is 20mM) and 0.12g Gitkutella (final concentration is 30mg / mL), Reacted at 35°C and 180rpm for 6h. After the reaction was over, the enantiomeric excess of the product (S)-phenylethylene glycol detected by HPLC was 98.67%, 98.38%, 99.99%, 99.99%, respectively. 99.99%, 99.99%.

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Abstract

The invention discloses a method for preparing (S)-phenyl-ethylene glycol by using microorganisms for asymmetric resolution. The method comprises the following steps that (1) an organic solvent and aphosphate buffer solution are mixed uniformly to obtain a two-phase system of the organic solvent and phosphate buffer solution; (2) (R,S)-phenyl-ethylene glycol and Kurthia gibsonii are added into the two-phase system obtained in step (1) to react with each other to obtain (S)-phenyl-ethylene glycol, wherein the Kurthia gibsonii is named Kurthia gibsonii SCO312, the preservation nmber is CCTCC NO:M2017157, and the strain is deposited on March 31, 2017 at the China Center for Type Culture Collection in Wuhan University, Wuhan, China. The application of the organic solvent / buffer solution two-phase system effectively inhibits the toxicity of the product, and increases the substrate concentration and product e. e. value of the reaction.

Description

technical field [0001] The invention belongs to the technical field of biocatalytic asymmetric resolution of chiral compounds, in particular to a method for preparing (S)-phenylethylene glycol through asymmetric resolution of microorganisms. Background technique [0002] Chiral alcohols are an important class of optically active compounds with unique chemical, light, and thermal stability. They are often used as important chiral raw materials and chiral intermediates in the fields of pesticides, materials, and medicine. Since the two enantiomers of chiral compounds are different in pharmacology, toxicology, and functional effects, the preparation of optically pure chiral modular compounds has extensive value in the fields of medicine, agriculture, materials, and environmental protection. Traditional chemical synthesis methods have achieved success in the synthesis research of many chiral compounds such as medicines, fine chemicals, and functional materials, and many differen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P7/22C12P41/00C12R1/01
CPCC12P7/22C12P41/001
Inventor 娄文勇赵莹彭飞宗敏华吴晓玲
Owner SOUTH CHINA UNIV OF TECH
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