Bacillus cercus and chiral 2,2-dimethyl cyclopropanecarboxylic acid/cyclopropancarboxamid prepared from the same

A technology of dimethylcyclopropanecarboxamide and dimethylcyclopropanecarboxylic acid is applied in the field of Bacillus cereus and the preparation of chiral 2,2-dimethylcyclopropanecarboxylic acid/amide, which can solve the problem of expensive chiral catalysts , environmental hazards, etc.

Active Publication Date: 2008-05-28
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using traditional chemical methods to prepare optically pure (S)-(+)-2,2-dimethylcyclopropanecarboxylic acid requires adding a large amount of solvents and expensive and toxic chiral catalysts in the reaction, which will cause great harm to the environment. harm

Method used

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  • Bacillus cercus and chiral 2,2-dimethyl cyclopropanecarboxylic acid/cyclopropancarboxamid prepared from the same
  • Bacillus cercus and chiral 2,2-dimethyl cyclopropanecarboxylic acid/cyclopropancarboxamid prepared from the same
  • Bacillus cercus and chiral 2,2-dimethyl cyclopropanecarboxylic acid/cyclopropancarboxamid prepared from the same

Examples

Experimental program
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Effect test

Embodiment 1

[0087] Embodiment 1: the isolation of bacterial strain

[0088] Isolation of S-amidase-producing bacteria: Add 1 g of soil sample (from Zhejiang Province) and appropriate amount of glass beads to 9 mL of 0.85% normal saline, shake well to form a uniform soil suspension; draw 0.5 mL of soil suspension Inoculate 250mL Erlenmeyer flask with 30mL enrichment medium, place in 30°C, 150rpm shaker for 4 days, wait for enrichment solution to become turbid, transfer 0.5mL to fresh medium , and continue to cultivate for 4 days; after repeating this for 4 to 5 cycles, dilute the enrichment solution into multiple gradients, spread it on the separation plate, and obtain a single colony;

[0089] The enrichment medium uses 2,2-dimethylcyclopropanamide as the only nitrogen source, and the composition is as follows (final concentration): KH 2 PO 4 0.5g / L, K 2 HPO 4 0.5g / L, MgSO 4 ·7H 2 O 0.5g / L, FeSO 4 ·7H 2 O0.03g / L, CaCl 2 0.03g / L, 2,2-Dimethylcyclopropylcarboxamide, 1.5g / L, pH 7.0,...

Embodiment 2

[0091] Embodiment 2: the cultivation of bacterial strain

[0092] Slant medium composition (final concentration): beef extract 5g / L, peptone 10g / L, NaCl 5g / L, agar 18g / L, prepared with tap water;

[0093] Pick a single colony of CCTCC No: M 207139 on the plate, inoculate it on the slant, culture it in a constant temperature incubator at 30°C for 48 hours, and store it in a refrigerator at 4°C for later use.

Embodiment 3

[0094] Embodiment 3: the acquisition of wet fungus cells

[0095] Medium preparation: glucose 15.8g, yeast powder 17.89g, 2,2-dimethylcyclopropanamide 3.47g, KH 2 PO 4 1g, K 2 HPO 4 1g, MgSO 4 ·7H 2 O 0.2g, FeSO 4 ·7H 2 O 0.03g; make up to 1L with tap water, pH 7.0;

[0096] In a 250ml shake flask with 30% liquid volume, inoculate a ring of CCTCC No: M 207139, shake and cultivate at 20°C and 150rpm for 72 hours; after the cultivation, the fermentation broth is centrifuged and washed twice with normal saline, and the wet bacterial cells are collected. The water content is 80%, suspended in 50mM, pH 7.8 phosphate buffer solution, and the bacterial suspension with a wet bacterial cell content of 0.5g / mL is obtained for future use.

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Abstract

The invention provides a new strain which is bacillus cereus ZJB-07112 and the application of the bacillus cereus in chiral catalysts preparation of (S)-(+)-2, 2- dimethyl cyclopropyl carboxylic acid and R-(-)-2, 2-dimethyl formamide. The invention has the advantages that a microbiological bacterial strain which contains amidase and the process for the chiral catalysts preparation of (S)-(+)-2, 2-dimethyl cyclopropyl carboxylic acid and R-(-)-2, 2-dimethyl formamide by using the microbiological bacterial strain, which has a perfect application prospect.

Description

(1) Technical field [0001] The present invention relates to a new strain-Bacillus cereus ZJB-07112 (Bacillus cereusZJB-07112), and its preparation of (S)-(+)-2,2-dimethylcyclopropanecarboxylic acid and Application of R-(-)-2,2-dimethylcyclopropylcarboxamide. (2) Background technology [0002] The combination of (S)-(+)-2,2-dimethylcyclopropanecarboxylic acid and ammonia can generate (S)-(+)-2,2-dimethylcyclopropaneamide. (S)-2,2-Dimethylcyclopropylcarboxamide is a key chiral intermediate in the synthesis of cilastatin. Cilastatin, the chemical name is (Z)-7-[(2R)-(2amino-2-carboxyethyl)sulfur]-[(1S)-2,2-dimethylcyclopropylcarboxamide] -2-heptenoic acid, is the first clinical renal dehydropeptidase inhibitor. Tienam, a compound preparation of cilastatin and imipenem, is a broad-spectrum β-lactam antibiotic developed by Merck in 1979. It was first introduced in Germany in 1985. listed. R-(-)-2,2-Dimethylcyclopropylcarboxamide can be used as a resolution reagent for chiral...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12N1/20C12P7/40C12P13/02C12R1/085
Inventor 郑裕国沈寅初张俊伟
Owner ZHEJIANG UNIV OF TECH
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