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Method for preparing duloxetine chiral intermediate through microbial conversion

A technology for microbial transformation and chiral intermediates, applied in microorganism-based methods, biochemical equipment and methods, microorganisms, etc., can solve problems such as not ideal paths, achieve easy large-scale industrial production, improve transformation efficiency, and be environmentally friendly. Effect

Active Publication Date: 2012-08-22
瑞博(杭州)医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Therefore, the lipase resolution racemate method is not an ideal way for the industrialized preparation of (S)-3-hydroxyl-3-(2-thienyl)propionitrile

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The CGMCC No. 2266 strain was inoculated into the slant medium, and cultivated at 30 ℃ for 4-6 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 ℃ and 180 r / min for 24 h to obtain a seed solution. Inoculate 10 mL of seed solution (inoculation amount based on the volume fraction of medium 10%) in a 250 mL Erlenmeyer flask containing 100 mL of liquid culture medium, and culture for 24 h at 30 ℃ and 180 r / min to obtain fermentation broth. Centrifuge the fermentation broth to obtain enzyme-containing bacterial cells.

[0040] The dry weight of the bacteria is determined by centrifuging the fermentation broth and taking a small part from the wet bacteria of the enzyme-containing bacteria cells and drying them at 120 ℃ for 48 hours to a constant weight. The weight of the dry cells is measured and the unit c...

Embodiment 2

[0046] The CGMCC No. 2266 strain was inoculated into the slant medium, and cultivated at 30 ℃ for 4-6 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 ℃ and 180 r / min for 24 h to obtain a seed solution. Inoculate 10 mL of seed solution (the inoculum volume is calculated as 10% of the volume of the medium) in a 250 mL Erlenmeyer flask containing 100 mL of liquid culture medium, and culture for 24 h at 30 ℃ and 180 r / min 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.

[0047] The wet cells obtained after centrifugation of the above 400 ml fermentation broth were added to ten Erlenmeyer flasks each containing 100 mL pH 7.0 phosphate buffer. T...

Embodiment 3

[0051] The Saccharomyces cerevisiae CGMCC No. 2266 strain was inoculated into the slant medium, and cultivated at 30 ℃ for 4-6 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 ℃ and 180 r / min for 24 h to obtain a seed solution. Inoculate 10 mL of seed solution (inoculation amount based on 10% of the volume of the medium) in a 250 mL Erlenmeyer flask containing 100 mL of liquid medium, and cultivate for 24 h at 30 ℃ and 180 r / min 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.

[0052] In five Erlenmeyer flasks each containing 100 mL of pH 7.0 phosphate buffer, add the wet cells obtained after centrifugation of the above 400 mL of fermentati...

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Abstract

The invention provides a method for preparing duloxetine chiral intermediate (S)-3-hydroxyl-3-(2-thineyl) propanenitrile through microbial conversion. The method comprises the following step of: converting 3-hydroxyl-3-(2-thineyl) propanenitrile into the (S)-3-hydroxyl-3-(2-thineyl) propanenitrile under the catalysis of enzyme-containing thallus cells obtained by fermentation of saccharomyces cerevisiae CGMCC No. 2266. The method has the advantages of mild reaction conditions, easiness and convenience for operation, low cost, high product yield, high purity and suitability for large-scale industrial production.

Description

Technical field [0001] The invention belongs to the field of microbial transformation, and specifically relates to a method for preparing duloxetine chiral intermediate (S)-3-hydroxy-3-(2-thienyl)propionitrile by microbial transformation. Background technique [0002] (S)-3-hydroxy-3-(2-thienyl) propanenitrile ((S)-3-hydroxy-3-(2-thienyl) propanenitrile), CAS registration number: 591727-36-5, molecular formula C 7 H 7 NOS, molecular weight 153. (S)-3-hydroxy-3-(2-thienyl)propionitrile is an important intermediate in the synthesis of antidepressant duloxetine. Duloxetine is a new type of antidepressant, a dual inhibitor of serotonin and norepinephrine reuptake. It has been discovered that it can not only treat depression, but also treat stress urinary incontinence and diabetic peripheral neuropathic pain. It also has a certain effect on chronic pain associated with depression. [0003] Ahmed Kamal, G. B. et al. in Tetrahedron Letters 44 (2003) 4783-4787 disclosed a route to prepar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/00C12R1/865
Inventor 沈文和欧志敏车大庆
Owner 瑞博(杭州)医药科技有限公司
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