Title:
CYCLOHEXANECARBOXYLATE HYDROLASE, AND MUTANT, CODING GENE, EXPRESSION VECTOR, RECOMBINANT BACTERIUM, AND APPLICATION THEREOF
Document Type and Number:
WIPO Patent Application WO/2022/016597
Kind Code:
A1
Abstract:
A cyclohexanecarboxylate hydrolase, and a mutant, a coding gene, an expression vector, a recombinant bacterium, and an application thereof. The cyclohexanecarboxylate hydrolase AcEst1 and the mutant thereof have the function of preparing optically active (S)-3-cyclohexene-1-carboxylic acid by efficient enantioselective resolution of 3-cyclohexene-1-carboxylate. When a substrate concentration is up to 2000mM (about 280g/L), the optical purity of the product is higher than 99%, and a substrate/catalyst is up to 3500g/g. With respect to other preparation methods, the product prepared by using the present method has a high concentration, a good optical purity, high catalyst efficiency, mild reaction conditions, environmental friendliness, simple operation, and easy industrial scale-up, and therefore has good industrial application prospects.
Inventors:
NI YE (CN)
DOU ZHE (CN)
XU GUOCHAO (CN)
DOU ZHE (CN)
XU GUOCHAO (CN)
Application Number:
PCT/CN2020/105687
Publication Date:
January 27, 2022
Filing Date:
July 30, 2020
Export Citation:
Assignee:
UNIV JIANGNAN (CN)
International Classes:
C12N9/18; C12N1/21; C12N15/55; C12N15/70; C12P41/00
Foreign References:
| CN110272839A | 2019-09-24 | |||
| CN1408848A | 2003-04-09 | |||
| CN106119303A | 2016-11-16 |
Other References:
DATABASE PROTEIN 18 June 2018 (2018-06-18), ANONYMOUS : "esterase [Acinetobacter johnsonii] ", XP055889367, retrieved from NCBI Database accession no. PZQ90293
TANYELI, C. TURKUT, E.: "Enzyme catalyzed reverse enantiomeric separation of methyl (+/-)-3-cyclohexene-1-carboxylate", TETRAHEDRON ASYMMETRY, PERGAMON PRESS LTD, OXFORD, GB, vol. 15, no. 13, 5 July 2004 (2004-07-05), OXFORD, GB , pages 2057 - 2060, XP004520142, ISSN: 0957-4166, DOI: 10.1016/j.tetasy.2004.05.034
XU CHUNXIU, YU SHI, SHI-YU ZHANG, RI LIU, CHAO XIA, HUI-QIANG WEI, LI YI-LIANG: "Chiral resolution of cyclohex-3-ene-1-carboxylic acid", DRUGS & CLINIC, vol. 28, no. 2, 31 March 2013 (2013-03-31), pages 126 - 128, XP055889371, ISSN: 1674-5515, DOI: 10.7501/j.issn.1674-5515.2013.02.006
KIM HYE EUN, LEE IN SOO, KIM JOO HWAN, HAHN KYU WOONG, PARK UL JAE, HAN HYON SOO, PARK KYEONG RYANG: "Gene Cloning, Sequencing, and Expression of an Esterase from Acinetobacter lwoffii I6C-1", CURRENT MICROBIOLOGY, SPRINGER-VERLAG, NEW YORK, vol. 46, no. 4, 1 April 2003 (2003-04-01), New York , pages 291 - 295, XP055889375, ISSN: 0343-8651, DOI: 10.1007/s00284-002-3886-3
WU XIAFEN, YANG SHENGLI, YU HONGWEI, YE LIDAN, SU BINGMEI, SHAO ZEHUI: "Improved enantioselectivity of E. coli BioH in kinetic resolution of methyl ( S )-3-cyclohexene-1-carboxylate by combinatorial modulation of steric and aromatic interactions", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY, JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY, AND AGROCHEMISTRY, JP, vol. 83, no. 7, 3 July 2019 (2019-07-03), JP , pages 1263 - 1269, XP055889378, ISSN: 0916-8451, DOI: 10.1080/09168451.2019.1597620
DOU ZHE; XU GUOCHAO; NI YE: "A novel carboxylesterase from Acinetobacter sp. JNU9335 for efficient biosynthesis of Edoxaban precursor with high substrate to catalyst ratio", BIORESOURCE TECHNOLOGY, ELSEVIER, AMSTERDAM, NL, vol. 317, 10 August 2020 (2020-08-10), AMSTERDAM, NL , XP086277047, ISSN: 0960-8524, DOI: 10.1016/j.biortech.2020.123984
TANYELI, C. TURKUT, E.: "Enzyme catalyzed reverse enantiomeric separation of methyl (+/-)-3-cyclohexene-1-carboxylate", TETRAHEDRON ASYMMETRY, PERGAMON PRESS LTD, OXFORD, GB, vol. 15, no. 13, 5 July 2004 (2004-07-05), OXFORD, GB , pages 2057 - 2060, XP004520142, ISSN: 0957-4166, DOI: 10.1016/j.tetasy.2004.05.034
XU CHUNXIU, YU SHI, SHI-YU ZHANG, RI LIU, CHAO XIA, HUI-QIANG WEI, LI YI-LIANG: "Chiral resolution of cyclohex-3-ene-1-carboxylic acid", DRUGS & CLINIC, vol. 28, no. 2, 31 March 2013 (2013-03-31), pages 126 - 128, XP055889371, ISSN: 1674-5515, DOI: 10.7501/j.issn.1674-5515.2013.02.006
KIM HYE EUN, LEE IN SOO, KIM JOO HWAN, HAHN KYU WOONG, PARK UL JAE, HAN HYON SOO, PARK KYEONG RYANG: "Gene Cloning, Sequencing, and Expression of an Esterase from Acinetobacter lwoffii I6C-1", CURRENT MICROBIOLOGY, SPRINGER-VERLAG, NEW YORK, vol. 46, no. 4, 1 April 2003 (2003-04-01), New York , pages 291 - 295, XP055889375, ISSN: 0343-8651, DOI: 10.1007/s00284-002-3886-3
WU XIAFEN, YANG SHENGLI, YU HONGWEI, YE LIDAN, SU BINGMEI, SHAO ZEHUI: "Improved enantioselectivity of E. coli BioH in kinetic resolution of methyl ( S )-3-cyclohexene-1-carboxylate by combinatorial modulation of steric and aromatic interactions", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY, JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY, AND AGROCHEMISTRY, JP, vol. 83, no. 7, 3 July 2019 (2019-07-03), JP , pages 1263 - 1269, XP055889378, ISSN: 0916-8451, DOI: 10.1080/09168451.2019.1597620
DOU ZHE; XU GUOCHAO; NI YE: "A novel carboxylesterase from Acinetobacter sp. JNU9335 for efficient biosynthesis of Edoxaban precursor with high substrate to catalyst ratio", BIORESOURCE TECHNOLOGY, ELSEVIER, AMSTERDAM, NL, vol. 317, 10 August 2020 (2020-08-10), AMSTERDAM, NL , XP086277047, ISSN: 0960-8524, DOI: 10.1016/j.biortech.2020.123984
Attorney, Agent or Firm:
CENTRAL SOUTH WELL INTELLECTUAL PROPERTY OFFICE (CN)
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