Acinetobacter and use thereof in production of chiral 3-cyclohexene-1-carboxylic acid

Patent metadata

Field	Value
Publication number	US-11441133-B2
Application number	US-201915734969-A
Country	US
Kind code	B2
Filing date	Nov 22, 2019
Priority date	May 8, 2019
Publication date	Sep 13, 2022
Grant date	Sep 13, 2022

Abstract

The invention discloses a strain of Acinetobacter and use thereof in the production of chiral 3-cyclohexene-1-carboxylic acid. Its taxonomic name is Acinetobacter sp., which is deposited on Jan. 21, 2019 at the China General Microbiological Culture Collection Center, under accession number CGMCC No. 17220. Using the Acinetobacter strain of the invention to produce chiral methyl 3-cyclohexene-1-carboxylate, the resulting methyl (S)-3-cyclohexene-1-carboxylate has an optical purity of 99% or more, and the catalyst has good stability, mild reaction condition and can withstand high concentrations of substrate and product. Using the resolution process of the invention, (S)-3-cyclohexene-1-carboxylic acid with high optical purity and high concentration can be simply and efficiently obtained, and the process is energy-saving and environmentally friendly, and the high-concentration of product is beneficial to downstream product recovery process. The invention provides an efficient method for production of (S)-3-cyclohexene-1-carboxylic acid, and has a good industrial application prospect.

First claim

What is claimed is:

1. A method for preparing (S)-3-cyclohexene-1-carboxylic acid, comprising:
isolating a strain of Acinetobacter , wherein a taxonomic name thereof is Acinetobacter sp., deposited on Jan. 21, 2019 at the China General Microbiological Culture Collection Center, located at No. 1, Beichen West Road, Chaoyang District, Beijing, under accession number CGMCC No. 17220;
producing an esterase by fermenting of the strain of Acinetobacter sp.; and
using the esterase as a catalyst to catalyze a reaction for producing the (S)-3-cyclohexene-1-carboxylic acid from a methyl (R,S)-3-cyclohexene-1-carboxylate.

2. The method according to claim 1 , wherein the catalysis specifically comprising catalyzing the enantioselective hydrolysis of the methyl (R,S)-3-cyclohexene-1-carboxylate in a buffer solution containing a cosolvent, and then collecting a methyl (S)-3- cyclohexene-1-carboxylate from the resulting mixture after hydrolysis, and performing hydrolysis of the said methyl (S)-3-cyclohexene-1-carboxylate by heating under an alkaline condition to obtain the (S)-3-cyclohexene-1-carboxylic acid.

3. The method according to claim 2 , wherein the cosolvent is an organic solvent mutually soluble with water.

4. The method according to claim 2 , wherein amount of the cosolvent added is 5-35% of the total volume of the solution.

5. The method according to claim 2 , wherein the buffer solution is citrate buffer, phosphate buffer or glycine-NaOH buffer, and has a pH of 5.0-9.5.

6. The method according to claim 2 , wherein the alkaline condition is a 0.5-1.5 M NaOH solution.

Assignees

• Univ Jiangnan

Inventors

• Ni Ye
• Dou zhe
• Xu Guochao

Classifications

• C12Y114/19001

  Stearoyl-CoA 9-desaturase (1.14.19.1), i.e. DELTA9-desaturase · CPC title

• C12N9/18 Primary

  Carboxylic ester hydrolases {(3.1.1)} · CPC title

• C12P7/40

  containing a carboxyl group {including Peroxycarboxylic acids} · CPC title

• C12R2001/01

  Bacteria or Actinomycetales {; using bacteria or Actinomycetales} · CPC title

• C12N1/205

  Bacterial isolates · CPC title