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A kind of preparation method of chiral benzyl sulfoxide

A phenylmethyl sulfoxide and chiral technology, applied in the field of preparation of chiral phenylsulfoxide, can solve the problems of many by-products, excessive oxidation, harsh reaction conditions, etc.

Inactive Publication Date: 2017-11-03
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] It is currently known that in addition to some metal catalysts that can effectively catalyze the asymmetric oxidation reaction of thioether substrates, most transition metal catalysts or organic small molecule catalysts still have excessive oxidation in the asymmetric oxidation reaction of thioether substrates. , many by-products and harsh reaction conditions

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] A preparation method of chiral benzyl sulfoxide includes the following steps:

[0017] (1) Preparation of strains: Pseudomonas monteilii CCTCC M2013683 was streaked on the LB medium plate sterilized at 121℃ for 20 min, and then cultured at 28℃ for 12 h. Then a single colony was picked and used as a seed to streak on the M9 medium plate. Toluene induced static culture to grow 24 After h, store at 4 ℃ for later use;

[0018] (2) Cell culture: Pick the seeds from the above M9 medium plate culture and inoculate them into 10 mL LB medium (peptone 10.0 g, yeast extract 5.0 g, sodium chloride 10.0 g, agar 15.0 g, and distilled water 1.0 L) , PH 6.8-7.0) in a 50 mL shake flask, cultured at 30 ℃ and 200 rpm for 8 hours, and then inoculated with the standard inoculum according to the initial OD value of the secondary induced culture broth of 0.1 50 mL of M9 medium (17.1 g of disodium hydrogen phosphate dodecahydrate, 3.0 g of potassium dihydrogen phosphate, 0.5 g of sodium chloride...

Embodiment 2

[0024] A preparation method of chiral benzyl sulfoxide includes the following steps:

[0025] (1) Preparation of strains: Pseudomonas monteilii CCTCC M2013683 was streaked on the LB medium plate sterilized at 121℃ for 20 minutes, and then cultured at 28℃ for 12 h. Then a single colony was picked and used as a seed to streak on the M9 medium plate. Toluene induced static culture to grow 24 After h, store at 4 ℃ for later use;

[0026] (2) Cell culture: Pick the seeds of the above M9 medium plate culture, and inoculate them into 10 mL LB medium (peptone 10.0 g, yeast extract 5.0 g, sodium chloride 10.0 g, agar 15.0 g, distilled water 1.0 L) , PH 6.8-7.0) in a 50 mL shake flask, cultured at 30 ℃ and 200 rpm for 8 hours, and then inoculated with the standard inoculum according to the initial OD value of the secondary induced culture broth of 0.1 50 mL of M9 medium (17.1 g of disodium hydrogen phosphate dodecahydrate, 3.0 g of potassium dihydrogen phosphate, 0.5 g of sodium chloride,...

Embodiment 3

[0032] A preparation method of chiral benzyl sulfoxide includes the following steps:

[0033] (1) Preparation of strains: Pseudomonas monteilii CCTCC M2013683 (select unique soil and activated sludge samples from the southwestern region, using multiple enrichment cultures and isolation of the resulting strains) Streak on the LB medium plate sterilized at 121 ℃ for 20 min, and culture at 28 ℃ 12 After h, pick a single colony, streak it on the M9 medium plate as a seed, induce static culture with toluene, grow for 24 h and store it at 4 ℃ for later use;

[0034] (2) Cell culture: Pick the seeds of the above M9 medium plate culture, and inoculate them into 10 mL LB medium (peptone 10.0 g, yeast extract 5.0 g, sodium chloride 10.0 g, agar 15.0 g, distilled water 1.0 L) , PH 6.8-7.0) in a 50 mL shake flask, cultured at 30 ℃ and 200 rpm for 8 hours, and then inoculated with the standard inoculum according to the initial OD value of the secondary induced culture broth of 0.1 50 mL of M...

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Abstract

The invention discloses a preparation method of chiral benzyl sulfoxide, which comprises the following steps: marking Pseudomonas monteilii ZMU‑T05 with the preservation number: CCTCC NO: M2013683 on an LB medium plate sterilized at 121°C for 20 min After static culture at 28 °C for 12 h, a single colony was picked and streaked on an M9 medium plate as a seed, induced by toluene for static culture, and stored at 4 °C after 24 h of growth; conventional cell culture; conventional biotransformation. The product obtained by the invention has high optical purity, low cost, safety and environmental protection.

Description

Technical field [0001] The invention relates to the technical field of biocatalysis and chiral synthesis, in particular to a method for preparing chiral benzyl sulfoxide. Background technique [0002] As a class of important biologically active substances and clinical drugs, chiral sulfoxides are widely used in organic synthesis and drug synthesis. Chiral sulfoxides are an important class of biologically active substances and clinical drugs, and monooxygenases catalyze the asymmetric oxidation of thioether substrates, which is one of the new ways to synthesize sulfoxides. The discovery and acquisition of thioether monooxygenase producing strains with high activity, high selectivity and high substrate tolerance are still difficulties and bottlenecks in the development of biological oxidation reactions. [0003] It is currently known that in addition to some metal catalysts that can effectively catalyze the asymmetric oxidation reaction of thioether substrates, most of the current t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P11/00C12R1/38
Inventor 陈永正卓俊睿郑代军杨敏
Owner ZUNYI MEDICAL UNIVERSITY
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