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Brevibacterium and hydrolytic synthesis method of alpha-cyclo hexyl mandelic acid through nitrile and derivative

A technology of cyclohexylmandelic acid and Brevibacterium, applied in the field of microorganisms, achieves the effects of mild reaction conditions, no by-products, high conversion rate, and simple process route

Active Publication Date: 2013-05-15
江苏溢坤医疗科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the use of α-cyclohexylmandelonitrile hydrolase to catalyze the synthesis of α-cyclohexylmandelic acid with high optical purity (e.e.>99.9%), and to screen new α-cyclohexylmandelonitrile hydrolases Strains become a priority

Method used

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  • Brevibacterium and hydrolytic synthesis method of alpha-cyclo hexyl mandelic acid through nitrile and derivative
  • Brevibacterium and hydrolytic synthesis method of alpha-cyclo hexyl mandelic acid through nitrile and derivative
  • Brevibacterium and hydrolytic synthesis method of alpha-cyclo hexyl mandelic acid through nitrile and derivative

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Experimental program
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Effect test

Embodiment 1

[0023] Brevibacterium Sp. CCZU12-1 quiescent cells catalyze the hydrolysis of α-cyclohexylmandelonitrile to produce α-cyclohexylmandelic acid

[0024] Prepare seed 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 phenylacetonitrile 0.1 g, water 1000 mL, pH 6.0), fill 250 mL medium in a 1 L shake flask, and culture at 160 rpm and 25 °C Brevibacterium sp. CCZU12-1 for 48 h, centrifuged and washed to obtain resting cells. Weigh 0.1 g of resting cells with a wet weight, suspend the cells in 1.0 mL of pH 6.0 potassium phosphate buffer solution, add α-cyclohexylmandelonitrile to a final concentration of 100 mM, shake at 25 °C and 120 rpm on a constant temperature shaker reaction. Such as figure 1 Shown, 48 h R - The analytical yield of α-cyclohexylmandelic acid was 49.3%, e.e. >99.9%.

[0025]

Embodiment 2

[0027] Brevibacterium Catalysis of different nitriles and their derivatives by sp. CCZU12-1 resting cells

[0028] 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 phenylacetonitrile 1 g, water 1000 mL, pH 9.0), fill 250 mL medium in a 1 L shake flask, and culture at 160 rpm and 35 °C Brevibacterium sp. CCZU12-1 for 48 h, centrifuged and washed to obtain resting cells. Weigh 0.01 g resting cells with a wet weight, suspend the cells in 1.0 mL pH 8.0 potassium phosphate buffer solution, add different substrate nitriles to a final concentration of 20 mM, shake at 35 °C and 160 rpm on a constant temperature shaker After reacting for 12 h, the product results are shown in Table 2.

[0029]

[0030] Table 2 Expansion of the substrate spectrum

[0031]

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Abstract

The invention discloses brevibacterium and a hydrolytic synthesis method of alpha-cyclo hexyl mandelic acid through nitrile and a derivative, which belongs to microbe technical field. A preservation number of brevibacterium sp.CCZU12-1 is CGMCCNo. 7042, and the brevibacterium is suggested to be classified and named brevibacterium sp.. alpha-cyclohexyl mandelonitrile and its derivative are taken as an initial raw material, a brevibacterium sp.CCZU12-1 resting cell is taken as a biocatalyst, and then the biosynthesis of alpha-cyclo hexyl mandelic acid and its derivative can be carried out under certain condition. The method provided by the invention has the characteristics of simple technical route, mild reaction condition and no pollution.

Description

technical field [0001] The invention discloses a nitrilase-producing bacterium isolated from soil Brevibacterium sp. CCZU12-1 and its method for catalyzing nitrile hydrolysis to synthesize optically pure α-cyclohexylmandelic acid and its derivatives belong to the technical field of microorganisms. Background technique [0002] Chiral α-cyclohexylmandelic acid can not only be used to synthesize antispasmodics such as oxybutynin and desethyloxybutynin, but also can be used to synthesize anticholinergics such as orphenium bromide and oxybenzidine; comparing their With a racemic structure, optically active drugs have more potent pharmacological effects. Therefore, the market prospect of single enantiomer α-cyclohexylmandelic acid is very huge. α-cyclohexylmandelic acid is an important intermediate in organic synthesis, widely used in the synthesis of pesticides and medicines. With the continuous expansion of its market, the demand for α-cyclohexylmandelic acid continues to i...

Claims

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Application Information

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IPC IPC(8): C12N1/20C12P7/42C12R1/13
Inventor 何玉财徐晓锋马翠鸾马江涛陈琳方月刘峰
Owner 江苏溢坤医疗科技有限公司
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