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Method for preparing (3S)-3-(tertbutyloxycarbonyl)amino-1-chlorin-4-phenyl-(2R)-butanol by microbial transformation

A technology for the conversion of tert-butoxycarbonyl and microorganisms, applied in the direction of microorganism-based methods, biochemical equipment and methods, microorganisms, etc., can solve the problems of large environmental pollution, cumbersome preparation process, and high price, and achieve high molar conversion rate, Environmentally friendly and low cost effect

Inactive Publication Date: 2012-10-17
ZHEJIANG JIUZHOU PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, chemical asymmetric reduction requires the preparation of chiral chemical catalysts, which is expensive, cumbersome to prepare, and usually causes greater environmental pollution.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The Saccharomyces cerevisiae CGMCC No. 2266 strain was inoculated into the slant medium and cultured at 30°C for 6 days to prepare the slant. Use an inoculating needle to take an inoculum loop from the slant surface of the bacteria and inoculate it in a 250 mL Erlenmeyer flask containing 100 mL of liquid culture medium, and incubate at 30°C and 180 r / min for 24 h to obtain a seed solution. Inoculate 10 mL of seed liquid (the inoculum amount is 10% of the volume of the liquid medium) in a 250 mL Erlenmeyer flask containing 100 mL of liquid medium, and cultivate it at 30°C and 180 r / min for 24 h to obtain fermentation broth. Centrifuge the liquid to obtain enzyme-containing bacterial cells.

[0031] It was determined that the dry weight of the enzyme-containing bacterial cells per liter of fermentation broth in this example was 50 grams.

[0032] Add 200 mL of the fermentation broth obtained above into ten Erlenmeyer flasks containing 100 mL of pH 7.0 phosphate buffer. The dr...

Embodiment 2

[0037] The Saccharomyces cerevisiae CGMCC No. 2266 strain was inoculated into the slant medium and cultured at 30°C for 6 days to obtain the slant. Use an inoculating needle to take an inoculum loop from the slant surface of the bacteria and inoculate it in a 250 mL Erlenmeyer flask containing 100 mL of liquid culture medium, and incubate it at 30 ℃ and 180 r / min for 24 h to obtain a seed solution. Inoculate 10 mL of seed solution (the inoculum amount is 10% of the volume of the liquid medium) in a 250 mL Erlenmeyer flask containing 100 mL of liquid medium, and cultivate it at 30 ℃ and 180 r / min for 24 h to obtain fermentation broth. The fermentation broth is centrifuged to obtain enzyme-containing bacterial cells, and the dry weight of the enzyme-containing bacterial cells per liter of fermentation broth is 50 grams.

[0038] Add 200 mL of the fermentation broth obtained above into seven Erlenmeyer flasks containing 100 mL pH 7.0 phosphate buffer. The dry weight of the enzyme-co...

Embodiment 3

[0043] The Saccharomyces cerevisiae CGMCC No. 2266 strain was inoculated into the slant medium and cultured at 30°C for 6 days to obtain the slant. Use an inoculating needle to take an inoculum loop from the slant surface of the bacteria and inoculate it in a 250 mL Erlenmeyer flask containing 100 mL of liquid culture medium, and incubate at 30°C and 180 r / min for 24 h to obtain a seed solution. The seed solution was inoculated into a 250 mL Erlenmeyer flask containing 100 mL of liquid culture medium with 10% of the inoculum, and cultured at 30 ℃ and 180 r / min for 24 h to obtain fermentation broth. The fermentation broth was centrifuged to obtain enzyme-containing bacteria Somatic cells, the dry weight of enzyme-containing bacterial cells per liter of fermentation broth is 50 grams.

[0044] Add 200 mL of the fermentation broth obtained above into five Erlenmeyer flasks containing 100 mL of pH 7.0 phosphate buffer. The dry weight of the enzyme-containing bacterial cells is 10 g. ...

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Abstract

The invention provides a method for preparing (3S)-3-(tertbutyloxycarbonyl)amino-1-chlorin-4-phenyl-(2R)-butanol by microbial transformation, comprising the following steps of: using (3S)-3-(tertbutyloxycarbonyl)amino-1-chlorin-4-phenyl-2-butanone as a substrate, using enzyme-containing somatic cells obtained by fermentation of saccharomyces cerevisiae (Saccharomycescerevisiae)CGMCCNo.2266 as a biocatalyst, and performing a conversion reaction to obtain the product. The strain produced by the invention is safe and nontoxic; and the microbial thallus is easy for large-scale culture and requires lower cost than a chemical catalyst and katalaze. In addition, the method provided by the invention requires mild reaction condition, is environmentally friendly, has high molar conversion rate, is easy to realize large-scale industrial production, and is a green technology for the industrial production of (3S)-3-(tertbutyloxycarbonyl)amino-1-chlorin-4-phenyl-(2R)-butanol.

Description

Technical field [0001] The invention relates to the field of microbial transformation methods, in particular to a method for preparing (3S)-3-(tert-butoxycarbonyl)amino-1-chloro-4-phenyl-(2R)-butanol by biocatalysis. Background technique [0002] (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-(2R)-butanol, English name: ((3S)-3-(tert-Butoxycarbonyl)amino-1-chloro -4-phenyl-(2R)-butanol), CAS number: 162536-40-5, molecular formula C 15 H 22 NClO 3 , Molecular weight 299.79. (3S)-3-(tert-butoxycarbonyl)amino-1-chloro-4-phenyl-(2R)-butanol is a key intermediate for preparing the anti-AIDS drug atazanavir. Atazanavir is a new type of azapeptide protease inhibitor (PI), designed based on the X-ray diffraction study of the enzyme-azapeptide complex, and has a C-2 symmetrical chemical structure. It is a highly selective and efficient inhibitor of HIV-1 protease. It inhibits the production of viral structural proteins, reverse transcriptase, integrase and protease by blocking the ...

Claims

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Application Information

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IPC IPC(8): C12P13/02C12N1/18C12R1/865
Inventor 沈文和欧志敏车大庆
Owner ZHEJIANG JIUZHOU PHARM CO LTD
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