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Method for biological catalysis of unsymmetrical reduction carbon based compound in water/ion liquid diphasic system

A carbonyl compound, ionic liquid technology, applied in microorganism-based methods, biochemical equipment and methods, microorganisms, etc., can solve the problems of low conversion rate and product concentration, difficulty in separation and recovery, microbial cytotoxicity, etc., and achieve conversion rate. and optical purity promotion, product separation is simple, and the effect of increasing product concentration

Inactive Publication Date: 2008-12-10
JIANGNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there are problems: 1) organic solvents are easy to cause environmental pollution; 2) enzymes are easily inactivated in polar organic solvents; 3) polar substrates have very little solubility in non-polar organic solvents
The successful approach of the method for preparing chiral alcohol by the reduction of the above two substrates known at present is the microbial cell catalyzed asymmetric reduction method (CN1778889A, CN1948499A) in the water / organic solvent two-phase system. Cell toxicity and instability in water / solvent, conversion rate and product concentration are not high, and the organic dibutyl phthalate selected by this method has a high boiling point, making separation and recovery difficult

Method used

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  • Method for biological catalysis of unsymmetrical reduction carbon based compound in water/ion liquid diphasic system
  • Method for biological catalysis of unsymmetrical reduction carbon based compound in water/ion liquid diphasic system
  • Method for biological catalysis of unsymmetrical reduction carbon based compound in water/ion liquid diphasic system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Choice of ionic liquid

[0034] A. Selection of Ionic Liquids in Aureobasidium pullulans CGMCC No.1244 Asymmetric Reduction of COBE to Form (S)-CBHE

[0035] Slant culture: the medium is 100mL wort, add 2g glucose, 2g agar, pH6.5, sterilize at 121°C for 20 minutes according to the usual method, cool down after sterilization to inoculate the slant, cultivate at 30°C for 2 days, and use it as an activated seed on the slant .

[0036] Seed cultivation and fermentation: medium: maltose 30g / L, yeast extract 20g / L, peptone 5g / L, (NH 4 ) 2 SO 4 5g / L, KH 2 PO 4 2g / L, MgSO 4 ·7H 2 O 0.7g / L, pH 6.0. The filling volume is 80mL of 500mL Erlenmeyer flask, sterilized at 121°C for 20 minutes, cooled and connected to slanted seeds after sterilization, shaken at 180 rpm, and cultivated at 30°C for 2 days, as seeds or fermentation enzyme liquid (whole cell catalyst).

[0037] The content of wet cells in the fermented enzyme liquid is 2.5g / 100mL, centrifuge for 10 minutes (8,000 ...

Embodiment 2

[0049] Effect of different phase volume ratios on transformation reactions in water / ionic liquid two-phase system

[0050] After Aureobasidium pullulans CGMCC No.1244 or grape juice yeast ATCC 26602 were cultured for 24 hours to produce enzyme according to the method in Example 1, weigh 1 g of wet bacteria and add 10 mL of 0.1 mol / L, pH 6.6 to 7.0 potassium phosphate buffer in a 150 mL Erlenmeyer flask , the substrate content is 30g / L, and the ionic liquid [bmim]PF with different phase volume ratios are added respectively 6 , the volume ratio of the ionic liquid to the buffer solution was 1:5, 5:5, 10:5, 15:5, 20:5, and the reaction was carried out at 30° C. and 180 rpm for 8 hours. After the reaction, the reaction solution was centrifuged to remove the bacteria and the water phase to obtain the ionic liquid phase, which was extracted three times with an equal volume of isopropanol, the combined extracts were dried with an appropriate amount of anhydrous magnesium sulfate, fil...

Embodiment 3

[0055] Effects of Different Temperatures on Transformation Reactions in Water / Ionic Liquid Two-Phase System

[0056] After Aureobasidium pullulans CGMCC No.1244 or grape juice yeast ATCC 26602 were cultured for 24 hours according to the method of Example 1, 1 g of wet bacteria was weighed and added to 5 mL of 0.1 mol / L, pH 6.6-7.0 potassium phosphate buffer in a 50 mL Erlenmeyer bottle In, with an equal volume of ionic liquid [bmim]PF 6 Mixed, the substrate content was 35g / L, and the effects of different temperatures on the conversion reaction were investigated respectively. The reaction was carried out at 20°C, 25°C, 30°C, 35°C, 40°C and 180 rpm for 8 hours. After the reaction, the reaction solution was centrifuged to remove the bacteria and the water phase to obtain an ionic liquid phase, which was extracted three times with an equal volume of isopropanol, and the extracts were combined, dried with an appropriate amount of anhydrous magnesium sulfate, filtered and then analy...

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Abstract

The invention discloses a method for asymmetrically reducing a carbonyl compound by biocatalysis in a water / ion liquid biphasic system, which belongs to the biochemical engineering technical field. The method takes a selective strain producing carbonyl reductase as a starting strain, and prochiral ketone as a substrate to perform reducing preparation of corresponding chiral alcohol in the water / ion liquid biphasic system; the method comprises the following steps that: Aureobasidium pullulans CGMCC No.1244 is used to catalyze 4-chloro-acetoacetic acid ethyl ester to perform the asymmetrical reduction preparation of (S)-4-chloro-3-hydroxybutyric acid ethyl ester, and Saccharoinyces uvarum ATCC 26602 is used to catalyze 4,4,4-trifluoroacetoacetate to perform the asymmetrical reduction preparation of (R)-4, 4, 4-trilfluoro-3-hydroxybutyrate. The method shows the advantages of no toxicity, no smell, difficult volatilization, good biocompatibility, no environmental pollution, simple product separation, easy recovery, repeated use and so on, of ion liquid. At the same time, the method improves the transformation rate, the concentration and an enantiomeric excess value of a reaction product, and quickens the process of the reaction.

Description

technical field [0001] The invention relates to a method for biocatalytic asymmetric reduction of carbonyl compounds in a water / ionic liquid two-phase system, belonging to the technical field of biochemical industry. The present invention relates to a new reaction system to effectively improve the preparation of chiral alcohols by catalytic asymmetric reduction reaction of microbial cells, especially the method for catalytic preparation of halogenated hydroxybutyrate, specifically, in the water / ionic liquid two-phase system Preparation of ethyl (S)-4-chloro-3-hydroxybutyrate by asymmetric reduction of ethyl 4-chloroacetoacetate catalyzed by Aureobasidium pullulans CGMCCNo.1244, and grape juice yeast (Saccharomyces uvarum) ATCC 26602 Catalyzed asymmetric reduction reaction of ethyl 4,4,4-trifluoroacetoacetate to prepare (R)-4,4,4-trifluoro-3-hydroxybutyric acid ethyl ester. Background technique [0002] Ionic liquids (ILs) are composed of positively charged ions and negative...

Claims

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Application Information

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IPC IPC(8): C12P7/62C12R1/645C12R1/85
Inventor 孙志浩倪晔郑璞张帆居年丰朱波林文清
Owner JIANGNAN UNIV
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