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Bacillus alcaligenes and method for preparing single enantiomer amygdalic acid

A technology of Alcaligenes, mandelic acid, applied in the directions of microorganism-based methods, biochemical equipment and methods, bacteria, etc., to achieve the effect of good catalytic effect

Inactive Publication Date: 2008-03-05
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The technical problem to be solved in the present invention is to disclose a kind of alcaligenes and its method for preparing single enantiomer mandelic acid, so as to overcome the above-mentioned defects in the prior art

Method used

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  • Bacillus alcaligenes and method for preparing single enantiomer amygdalic acid
  • Bacillus alcaligenes and method for preparing single enantiomer amygdalic acid
  • Bacillus alcaligenes and method for preparing single enantiomer amygdalic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1 Microbial Culture

[0059] Inoculate 50mL fermentation medium (10g of glycerol, 15g of peptone, 8g of yeast extract, KH 2 PO 4 4g, NaCl2g, MgSO 4 0.2g, FeSO 4 ·7H 2 (00.05g, tap water 1000mL, pH7.0) pre-cultured for 15h, with the culture solution as a seed, inoculated to 200mL fermentation medium with a 10% inoculum size, and cultivated on a shaker at 160rpm at 30°C for 48h.

Embodiment 2

[0060] Example 2 Preparation of (R)-(-)-mandelic acid by resting cells

[0061] Centrifuge the harvested Alcaligenes sp.ECU0401 cells at 12,000×g for 15 minutes to obtain resting cells with a wet weight of 100 g, suspend the cells in 1000 mL of potassium phosphate buffer solution, add 3.8 g of racemic mandelic acid, and the final concentration is 25mM, shaken at 30°C and 160rpm for 14 hours, then centrifuged the reaction solution at 12,000×g for 15min to remove cells. Add 2M H to the supernatant 2 SO 4 Acidify to a pH of 1.0-2.0, add salt to saturation, extract with an equal volume of ethyl acetate, repeat three times, combine the extracts, add anhydrous sodium sulfate to dry overnight, and remove the organic solvent by rotary evaporation to obtain a crude crystal, which is passed through a silica gel column layer Analysis (benzene: ethyl acetate: formic acid, volume ratio 10:2:1) to obtain (R)-(-)-mandelic acid after purification: white powder, yield 41.5%, e.e.>99.9%, spec...

Embodiment 3

[0062] Example 3 Catalytic synthesis of (R)-(-)-mandelic acid by growing cells

[0063] In 200mL medium (peptone 15g, yeast extract 8g, KH 2 PO 44 g, NaCl2g, MgSO 4 0.2g, FeSO 4 ·7H 2 (00.05g, 1000mL of tap water, pH7.0) add 2g racemic mandelic acid, cultivate Alcaligenes sp.ECU040148 hours at 30 ℃ and constant temperature shaker of 160rpm, fermented liquid is centrifuged 15min with 12,000 * g, Remove cells. Add 2M H to the supernatant 2 SO 4 Acidify to a pH of 1.0-2.0, add salt to saturation, extract with an equal volume of ethyl acetate, repeat three times, combine the extracts, add anhydrous sodium sulfate to dry overnight, and remove the organic solvent by rotary evaporation to obtain a crude crystal, which is passed through a silica gel column layer After purification by analysis (benzene: ethyl acetate: formic acid, volume ratio 10:2:1), pure (R)-(-)-mandelic acid was obtained: white powder, yield 40.5%, e.e.>99.9%.

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Abstract

The present invention discloses one kind of Bacillus alcaligenes and the process of preparing single antimer mandelic acid therewith. The resting cell of the Bacillus alcaligenes, ECU0401 CGMCC No.2009, is used as the biological catalyst in selectively converting racemized mandelic acid and its derivative to prepare optically active mandelic acid and its derivative. The Bacillus alcaligenes strain of the present invention has high catalyzing effect, and the product (R)-(-)-mandelic acid has optical purity over 99.9 %, obviously higher than that obtained with catalyzing yellow Bacillus brevis AS1.818 and with catalyzing Saccharomyces cervisiae AS2.150.

Description

technical field [0001] The invention relates to a strain of Alcaligenes and its application, especially a method for preparing single enantiomer mandelic acid. technical background [0002] Mandelic acid (α-hydroxyphenylacetic acid) is an important chiral intermediate. Compared with the racemate of mandelic acid, its single enantiomer (dextrorotatory or levorotatory mandelic acid) has higher usage value. Therefore, how to easily and efficiently obtain the single enantiomer of mandelic acid has become a research hotspot. [0003] (R)-(-)-Mandelic acid and its derivatives are an important class of chiral synthons for the synthesis of various drugs, and are widely used in the synthesis of various drugs, such as semi-synthetic antibiotics, cephalosporins, anti-tumor It is an important intermediate of anti-aging drugs, and can also be used as a chiral chiral reagent to resolve other chiral compounds. [0004] The chemical structure of (R)-(-)-mandelic acid is: [0005] [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12N1/20C12P7/42C12P41/00C12R1/05
Inventor 许建和何玉财潘江徐毅
Owner EAST CHINA UNIV OF SCI & TECH
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