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Rhodococcus erythropolis and application thereof in microbe-catalyzed preparation of chiral aromatic alcohol

A technology for Rhodococcus erythraea and aromatic alcohol is applied to Rhodococcus erythropolis and its application field in microbial catalyzed preparation of chiral aromatic alcohol, and achieves the effects of high conversion rate, little environmental pollution and strong reaction specificity

Active Publication Date: 2012-04-18
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no method for generating chiral aromatic alcohols by using Rhodococcus erythropolis microorganisms

Method used

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  • Rhodococcus erythropolis and application thereof in microbe-catalyzed preparation of chiral aromatic alcohol
  • Rhodococcus erythropolis and application thereof in microbe-catalyzed preparation of chiral aromatic alcohol
  • Rhodococcus erythropolis and application thereof in microbe-catalyzed preparation of chiral aromatic alcohol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The composition of the fermentation medium of Rhodococcus erythropolis WZ010 (CCTCC NO: M 2011336): peptone 1.0%, yeast extract 0.5%, NaCl 0.5%, solvent is water, pH 7.0-7.2, sterilized at 121°C for 20 min.

[0034] Rhodococcus erythropolis WZ010 was inoculated into 50ml fermentation medium, and cultured for 12 to 48 hours at 30°C and a shaker rotation speed of 200 rpm. After the fermentation broth was centrifuged at 6000 rpm for 15 minutes, the supernatant was discarded, and the cells were washed once with the reaction buffer, and the wet cells obtained were the biocatalyst.

Embodiment 2

[0036] The 2mL oxidation reaction system contained 50mM glycine-sodium hydroxide buffer (pH10.5), 0.18g Rhodococcus erythropolis wet cell, 40mM mixed 1-phenylethanol. React at different temperatures for 4 hours. After the reaction, the reaction solution was centrifuged at 6000 rpm for 15 min, and 1 mL of the supernatant was mixed with 1 mL of ethyl acetate in equal volumes, and then placed in a shaker for extraction at 30° C. and 200 rpm for 1 to 2 hours. Centrifuge the extract at 6000 rpm for 10 min, take 400 μL of the organic phase, and add excess anhydrous Na 2 SO 4 Dry, perform chiral gas chromatographic analysis of the substrate and its conversion products, see the results figure 1 .

[0037] by figure 1 The results show that Rhodococcus erythropolis WZ010 has catalytic activity for 1-phenylethanol at 4~60℃, and its catalytic activity is highest at 30℃.

Embodiment 3

[0039] In a 2mL oxidation reaction system, containing Tris-HCl buffer of pH 8.0~8.8 or glycine-sodium hydroxide buffer (50mM) of pH 8.8~11.0, 0.18g of wet rhodococcus rhodococcus, 40mM mixing 1-Phenylethanol. React at 30°C and different pH for 4 hours. After the reaction, the reaction solution was centrifuged at 6000 rpm for 15 min, and 1 mL of the supernatant was mixed with 1 mL of ethyl acetate in equal volumes, and then placed in a shaker for extraction at 30° C. and 200 rpm for 1 to 2 hours. Centrifuge the extract at 6000 rpm for 10 min, take 400 μL of the organic phase, and add excess anhydrous Na 2 SO 4 Dry, perform chiral gas chromatographic analysis of the substrate and its conversion products, see the results figure 2 .

[0040] by figure 2 The results show that Rhodococcus erythropolis WZ010 has activity between pH 8 and 11, and its catalytic activity increases with the increase of pH.

[0041] In the 2mL reduction reaction system, respectively containing pH 6.0~7.0 d...

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Abstract

The invention provides a novel bacterial strain - Rhodococcus erythropolis WZ010 and application thereof in selectively oxidizing racemic aromatic alcohol to prepare R-aromatic alcohol and asymmetrically reducing aromatic ketone to produce S-aromatic alcohol. The bacterial strain is preserved in China Center for Type Culture Collection, Wuhan University, Wuhan, China, the postcode is 430072, the preservation number is CCTCC No: M2011336, and the preservation date is 29 September, 2011. The invention mainly has the advantages that: the invention provides the novel bacterial strain with high stereoselectivity and high enzymatic activity, the R-aromatic alcohol and the S-aromatic alcohol can be obtained at the same time by selective oxidation and asymmetric reduction with the bacterial strain, the reaction specificity and catalytic activity of the bacterial strain are high, the production cost is greatly reduced, moreover, environment pollution is little, and the bacterial strain is suitable for industrialized production.

Description

(1) Technical field [0001] The invention relates to a new strain-Rhodococcus erythropolis WZ010, and its application in the selective oxidation of mixed aromatic alcohols to prepare R-type aromatic alcohols and the asymmetric reduction of aromatic ketones to generate S-type aromatic alcohols. (2) Background technology [0002] Chiral aromatic alcohols are a class of chiral alcohols with one or more benzene ring structures, and are important intermediates for more than 20 aromatic alcohol amine drugs. Among them, the more typical drugs are Isoproternol, Colterol, Phenylephrine, Bitolerol, and the latest antidepressant drugs Tomozetine, Fluoxetine and Nisoxetine. Both enantiomers of chiral aromatic alcohols can be used as intermediates in drug synthesis, and the effects are significantly different. For example, R-Fluoxetine is an antidepressant, while the S-isomer can prevent migraine. Both The efficacy is different; R-salbutamol is used to treat asthmatic bronchial inflammation, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12N1/20C12P41/00C12P7/22C12R1/01
Inventor 应向贤汪钊杨池熊斌
Owner ZHEJIANG UNIV OF TECH
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