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Process for preparing (R)-mandelic acid by microbial asymmetric reduction

A microbial method, asymmetric technology, applied in the field of asymmetric synthesis of chiral compounds by biological method, can solve the problems of many by-products, difficult separation of products and substrates, etc.

Inactive Publication Date: 2006-10-04
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Kaul et al. utilize nitrilase to asymmetrically hydrolyze mandelonitrile to prepare (R)-mandelic acid, but the highest yield can only reach 50%, and the separation of product and substrate is difficult
[0013] Oda et al. used 1,2-phenylethylene glycol as a substrate to obtain (R)-mandelic acid through asymmetric oxidation of β-hydroxyl, but the yield was only 40%, and there were many by-products, which were difficult to separate

Method used

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  • Process for preparing (R)-mandelic acid by microbial asymmetric reduction
  • Process for preparing (R)-mandelic acid by microbial asymmetric reduction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Cultivation of bacterial strains: the composition of the medium is that the components contained in each 100ml of culture solution are in g: glucose 2-6, yeast extract 0.25-1, (NH 4 ) 2 HPO 4 0.5~2.0,KH 2 PO 4 0.1~0.5, MgSO 4 ·7H 2 O 0.02~0.06, NaCl 0.0025~0.01, ZnSO 4 ·7H 2 O 0.001~0.005, FeSO 4 ·7H 2 O 0.001~0.005, CuSO 4 ·5H 2 O 0.0001~0.0005, MnSO 4 4H 2 O 0.00025~0.001.

[0061] The culture conditions are as follows: the initial pH is 6.0-8.0, the filling volume is 20%, the culture temperature is 30° C., the rotation speed of the shaking flask is 100-300 rpm, and the culture time is 48 hours.

Embodiment 2

[0063] Preparation of whole cells: Saccharomyces cerevisiae AS 2.150 was inoculated in a 250ml shake flask with a liquid volume of 20% and shaken at 30°C and 100-300rpm for 48 hours; After washing twice with saline, the collected cells were stored in a refrigerator at 4°C for transformation reactions.

Embodiment 3

[0065] Weigh 0.1g (5%) Saccharomyces cerevisiae AS 2.150 bacterial cells, place in 2mL potassium phosphate buffer containing 0.2mol / L, pH7.0 containing 5mg benzoylformic acid, add 0.01g glucose, 40 ℃, 150 rpm, transformed for 24 hours, centrifuged the transformed liquid, collected the supernatant, adjusted the pH to 1.0 with 3 mol / L hydrochloric acid, then extracted with 2.5 times the volume of ethyl acetate, and the separated ethyl acetate layer was washed with anhydrous Remove water with sodium sulfate, dry in vacuum at low temperature, dissolve the residual solid with a mixture of n-hexane and isopropanol (volume ratio 9:1), the product (R)-mandelic acid has an optical purity of 99.89% e.e, and a yield of 84.96%.

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Abstract

The asymmetrical reduction bio-method for (R)-mandelic acid comprises: screening the Saccharomyces cerevisiae AS 2.150 for culture and full cell preparation; with benzoylformic aicd as substrate, adding assist substrate, catalytic converting to obtain the product with optical purity up to 90%e.e. This invention improves product optical purity and yield, and has important meaning for enzyme development and resolution.

Description

technical field [0001] The invention discloses a method for preparing (R)-mandelic acid through asymmetric reduction of microorganisms, which belongs to the technical field of biological asymmetric synthesis of chiral compounds. Background technique [0002] Racemic mandelic acid (also known as α-hydroxyphenylacetic acid, English name Mandelic acid), is composed of two enantiomers of (R)-mandelic acid and (S)-mandelic acid, of which (R)-mandelic acid It is an important chiral intermediate and is widely used in the synthesis of various drugs, such as antibiotics such as penicillins and cephalosporins, weight-loss drugs, anti-tumor drugs, drugs for treating depression and pesticides, etc.; and can As a chiral reagent, it is used to resolve other chiral compounds. [0003] Chiral compounds play an important role in people's lives. Since the two enantiomers are different in pharmacology, toxicology and functional effects, the preparation of optically pure chiral modular compoun...

Claims

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Application Information

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IPC IPC(8): C12P7/42C12P41/00C12N1/14C12R1/865
Inventor 徐岩张辉
Owner JIANGNAN UNIV
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