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

A mandelic acid, asymmetric technology, applied in the field of biological separation of racemic compounds, can solve problems such as difficult separation, difficult separation of product and substrate, and many by-products

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 resolution

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Cultivation of bacterial strains: The composition of the medium is that the components contained in each 100ml of culture solution are in g: glucose 0.25-1.0, meat extract 0.5-2.0, peptone 0.5-2.0, yeast extract 0.1-0.5, (Nh 4 ) 2 HPO 4 0.5~1.0, KH 2 PO 4 0.25~0.5, MgSO 4 ·7H 2 O 0.025~0.1, NaCl 0.001~0.005, ZnSO 4 ·7H 2 O0.001~0.005, FeSO 4 ·7H 2 O 0.001~0.005, CuSO 4 ·5H 2 O 0.0001~0.0005, MnSO 4 4H 2 O 0.0001~0.0005.

[0062] 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

[0064] Preparation of whole cells: B.flavum AS 1.818 was inoculated in a 250ml shake flask with a liquid volume of 20%, and cultured at 30°C and 100-300rpm for 48 hours with shaking; after the cultivation, the cells in the fermentation broth were centrifuged and washed with normal saline Twice, the collected cells were stored in a 4°C refrigerator for splitting reactions.

Embodiment 3

[0066] Preparation of (R)-mandelic acid by asymmetric resolution by microbial method: in 2 mL of potassium phosphate buffer containing 10 mg of racemic mandelic acid at 0.2 mol / L, pH 7.0, add 0.1 g (i.e. weight to volume ratio 5%) B. flavumAS 1.818 bacterial cells, 25°C, 150 rpm, transformed for 72 hours, centrifuged the transformed solution, collected the supernatant, adjusted the pH to 1.0 with 3mol / L hydrochloric acid, extracted with 2.5 times the volume of ethyl acetate, and separated The ethyl acetate layer was dehydrated with anhydrous sodium sulfate, dried in vacuum at low temperature, and the residual solid was dissolved with a mixed solution of n-hexane and isopropanol (volume ratio of 9:1), and the product (R)-mandelic acid had an optical purity of 90.83 %e.e, yield 38.63%.

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Abstract

The asymmetrical resolution method for (R)-mandelic acid comprises: screening the (Brevibacterium flavum) AS 1.818 for culture and full cell preparation; with racemic acid as substrate, catalytic converting to obtain the product with optical purity up to 90%e.e. This invention improves product optical purity 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 separation by microorganisms, which belongs to the technical field of separation of racemic compounds by biological methods. 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 comp...

Claims

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Application Information

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IPC IPC(8): C12P7/42C12P41/00C12N1/20C12R1/13
Inventor 徐岩张辉
Owner JIANGNAN UNIV
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