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Method for preparing optical activity alcohol by using yeast cell to catalytically reduce aromatic ketone

A technology of optical activity and yeast cells, applied in biochemical equipment and methods, methods based on microorganisms, fermentation, etc., to achieve the effect of increasing reaction rate, shortening reaction time, and increasing stereoselectivity

Inactive Publication Date: 2008-08-13
JIANGSU LASON CHEM ENVIRONMENTAL PROTECTION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There have been patent applications for cyclodextrin biotransformation, and the Chinese patent (application number 200710056952.5) ​​applied by Tianjin University of Science and Technology "a method of sterol biotransformation using cyclodextrin and its application" is mainly aimed at the transformation of sterol biotransformation Period and conversion rate, not related to the issue of stereoselectivity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Example 1: Add 100 mL of pH 7.0 phosphate buffer and 17 g of dry yeast in an Erlenmeyer flask, shake (120 r / min) in a water bath constant temperature oscillator for 0.5 h at 33° C. to activate the baker’s yeast, and then Add 10mmolβ-cyclodextrin and 50mmol (6.0g / L) acetophenone, shake the reaction at the same temperature for 24h. After the reaction, add 20mL of ethyl acetate to the reaction solution, shake and extract and then centrifuge to separate the extract, add a certain amount of internal standard tridecane after the extract is concentrated, and then use the CP-Chirosil-DexCB As detected by gas chromatography on a chiral capillary column, the conversion rate of the substrate acetophenone and the enantiomeric excess value of the product S-1-phenylethanol are 95.8% and 94.3%, respectively.

Embodiment 2

[0013] Example 2: Add 100 mL of pH 7.0 phosphate buffer and 17 g of dry yeast in an Erlenmeyer flask, shake (120 r / min) in a water bath constant temperature oscillator for 0.5 h at 33 ° C to activate the baker's yeast, and then Add 3mmol hydroxypropyl-β-cyclodextrin and 50mmol (6.6g / L) propiophenone, shake and react at the same temperature for 24h. After the reaction, add 20mL of ethyl acetate to the reaction solution, shake and extract and then centrifuge to separate the extract, add a certain amount of internal standard tridecane after the extract is concentrated, and then use the CP-Chirosil-DexCB The gas chromatographic detection of the chiral capillary column shows that the conversion rate of the substrate propiophenone and the enantiomeric excess value of the product S-1-phenylpropanol are 81.3% and 78.1%, respectively.

Embodiment 3

[0014] Example 3: Add 100 mL of pH 7.0 phosphate buffer and 17 g of dry yeast in an Erlenmeyer flask, shake (120 r / min) in a water bath constant temperature oscillator for 0.5 h at 33 ° C to activate the baker's yeast, and then Add 15mmolβ-cyclodextrin and 50mmol (7.8g / L) p-chloroacetophenone, shake the reaction at the same temperature for 28h. After the reaction, add 20mL of ethyl acetate to the reaction solution, shake and extract and then centrifuge to separate the extract, add a certain amount of internal standard tridecane after the extract is concentrated, and then use the CP-Chirosil-DexCB The gas chromatographic detection of the chiral capillary column shows that the conversion rate of the substrate p-chloroacetophenone and the enantiomeric excess value of the product S-1-p-chlorophenylethanol are 50.9% and 97.4%, respectively.

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Abstract

A method for preparing optically active alcohol by yeast cell catalytic reduction aromatic ketone belongs to the technology field of preparing optically active alcohol in organism catalysis method. In the invention, a given amount of cyclodextrin is added into bioconversion system of yeast cell catalyzing unsymmetrical reduction aromatic ketone to form clathrate with aromatic ketone in order to efficiently improve the dissolvability of reaction bottom object in water and reduce properly the inhibitory action of bottom object and outcome for enzyme. The cyclodextrin improves the catalytic reduction efficiency of yeast juice, increases the stereo selectivity for bottom object, improves evidently thepercent conversion of bottom object and the antipode excess value of outcome. When bottom object concentration is 6-12g / L, different mole ratio cyclodextrin is added according to different bottom object, the percent conversion of bottom object aromatic ketone is 50-99and antipode excess value of outcome optically active alcohol is 75-99D:\˜ñθš€“ž\Àó†¸\�˜ÊÙ\2433biba_�˜13_sunquansheng(100“ž)\2433biba_�˜13_sunquansheng(100“ž).txto the product incorporating the invention has high practical application worthiness.

Description

technical field [0001] The invention discloses a method for preparing optically active alcohols by catalytically reducing aromatic ketones in yeast cells, which belongs to the technical field of preparing optically active alcohols by biocatalysis. Background technique [0002] Optically active alcohols are important intermediates for the synthesis of chiral compounds such as chiral drugs, pesticides, and food additives. The asymmetric reduction of prochiral ketones by chemical methods is an important way to prepare optically active alcohols. However, with the gradual depletion of ore resources and the increasing environmental pollution, the current biotransformation technology with the characteristics of high efficiency, specificity and green energy saving is in the market. Applications in asymmetric synthesis are gaining more and more attention. Microbial cells contain many stereoselective enzymes. Using the whole cell to catalyze the asymmetric reduction of prochiral keto...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/22C12R1/645
Inventor 刘湘张文虎夏咏梅张宝立刘士荣
Owner JIANGSU LASON CHEM ENVIRONMENTAL PROTECTION
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