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Method for synthesizing chiral sulfoxide from thioether under catalytic action of Rhodococcus

A technology for coccus-catalyzed thioether and Rhodococcus, applied in the field of microorganisms, can solve the problems that it is difficult to meet the high requirements for the purity of chiral natural products, the benzyl sulfoxide does not reach high optical purity, and achieves no by-products and conversion rate. High, mild reaction conditions, simple process route effect

Inactive Publication Date: 2013-05-22
临泉县嘉鸿装饰工程有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on S-sulfoxide catalyzed by monooxygenase in Rhodococcus sp. CCZU10-1 cells to oxidize sulfide anisole!
Although the Chinese patent (publication number CN101372676) reported that another strain of Rhodococcus Rhodococcus sp. >e.e.=99.0%), but a small amount of R-phenylsulfoxide was formed
S-Benzyl sulfoxide does not reach high optical purity (e.e.>99.9%), it is difficult to meet the high purity requirements in the synthesis of chiral natural products and chiral drugs Require

Method used

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  • Method for synthesizing chiral sulfoxide from thioether under catalytic action of Rhodococcus
  • Method for synthesizing chiral sulfoxide from thioether under catalytic action of Rhodococcus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Rhodococcus sp. CCZU10-1 quiescent cells catalyze the synthesis of thioanisole S -Benzyl sulfoxide

[0023] Prepare medium (glucose 5 g, peptone 5 g, yeast extract 5 g, KH 2 PO 4 1 g, NaCl 0.1 g, MgSO 4 0.1 g, inducer sulfide anisole 0.01 g, water 1000 mL, pH 6.0), put 3 L medium in a 5 L shake flask, culture at 160 rpm and 25 °C for 48 h, centrifuge, Resting cells are obtained by washing. Weigh 0.1 g resting cells with a wet weight, suspend the cells in 1.0 mL pH 6.0 potassium phosphate buffer solution, add a final concentration of 100 mM sulfide anisole, and shake the reaction at 25 °C and 160 rpm for 48 h ( figure 1 shown), S - Benzyl sulfoxide yield 51.3%, e.e. >99.9%.

[0024]

Embodiment 2

[0026] Rhodococcus Catalytic oxidation of different thioethers by sp. CCZU10-1 resting cells

[0027] Prepare medium (glucose 20 g, peptone 20 g, yeast extract 20 g, KH 2 PO 4 5 g, NaCl 1.5 g, MgSO 4 0.5 g, inducer sulfide anisole 10 g, water 1000 mL, pH 9.0), put 250 mL of culture medium in a 1 L shake flask, culture at 160 rpm and temperature 35 °C for 48 h, centrifuge, Resting cells are obtained by washing. Weigh 0.01 g of resting cells with a wet weight, suspend the cells in 1.0 mL of pH 8.0 potassium phosphate buffer solution, add different substrate thioethers to a final concentration of 20 mM, and place on a constant temperature shaker at 35 °C and 160 rpm Shaking reaction, after 12 h of reaction, the measurement results are shown in Table 1.

[0028] Table 1 Expansion of the substrate spectrum

[0029]

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Abstract

The invention discloses a method for synthesizing chiral sulfoxide from thioether under the catalytic action of Rhodococcus, belonging to the technical field of microorganisms. By using a resting cell of Rhodococcus sp. CCZU10-1 of which the collection number is CGMCC NO.4911 as a biocatalyst, asymmetric catalytic oxidation is performed on prochiral thioanisole and derivatives thereof, thus synthesizing chiral S-methyl phenyl sulfoxide (e.e.>99.9%) and derivatives thereof. The strain disclosed by the invention and the stereoselective biological oxidation method using the same have the characteristics of favorable catalytic effect, simple operating process route, mild reaction conditions, no pollution and the like.

Description

technical field [0001] The invention discloses that Rhodococcus isolated from soil is used to catalyze the synthesis of thioether S -Benzyl sulfoxide ( e.e. >99.9%) and their derivatives, which belong to the field of microbial technology. Background technique [0002] Chiral sulfoxide can be used as a chiral auxiliary agent and intermediate for the synthesis of complex chiral natural products; as a chiral ligand or chiral catalyst for a variety of asymmetric catalytic reactions; as a chiral drug for the treatment of gastric ulcer Proton pump inhibitors such as esomeprazole etc. Chiral sulfoxides have important and extensive uses. Chiral sulfoxides and their derivatives are widely used as important chiral intermediates and adjuvants, chiral ligands and catalysts, and chiral drugs. Chiral sulfoxides can be synthesized by biological and chemical methods, including induction of chiral auxiliary agents, chiral resolution and asymmetric catalysis. In contrast, the synthesi...

Claims

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Application Information

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IPC IPC(8): C12P11/00C12R1/01
Inventor 何玉财马翠鸾杨振兴周敏邢震马江涛陈琳方月刘峰
Owner 临泉县嘉鸿装饰工程有限公司
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