Title:
METHOD FOR PREPARING S-NICOTINE
Document Type and Number:
WIPO Patent Application WO/2023/015712
Kind Code:
A1
Abstract:
The present invention relates to the technical field of biosynthesis, and in particular to a method for preparing S-nicotine. Amine oxidase is utilized to oxidize 1-methylpyrrolidine into corresponding imine, and then the imine and nicotinic acid are condensed and decarboxylated under the catalysis of nicotine synthetase to obtain a final product S-nicotine. The S-nicotine having specific chirality can be obtained by means of two-step reaction in a reaction system, the synthetic route is short, the yield is high, the reaction conditions are mild, and large-scale production is easy to achieve; moreover, raw materials are wide in source, low in price, low in production cost and environmentally friendly, the production cost of nicotine is remarkably reduced, and the requirements of current green industrial production can be better satisfied.
Inventors:
ZHAO HONG (CN)
LING RUIMEI (CN)
FU LIN (CN)
YU TIEMEI (CN)
PAN JUNFENG (CN)
LIU JIAN (CN)
LING RUIMEI (CN)
FU LIN (CN)
YU TIEMEI (CN)
PAN JUNFENG (CN)
LIU JIAN (CN)
Application Number:
PCT/CN2021/123012
Publication Date:
February 16, 2023
Filing Date:
October 11, 2021
Export Citation:
Assignee:
SHENZHEN READLINE BIOTECH CO LTD (CN)
International Classes:
C12N9/06; C07D401/04; C12N9/00; C12N9/02; C12N9/08; C12N15/53; C12P17/16
Domestic Patent References:
| WO2020098978A1 | 2020-05-22 | |||
| WO2014174505A2 | 2014-10-30 | |||
| WO2016065209A2 | 2016-04-28 |
Foreign References:
| CN102816106A | 2012-12-12 | |||
| CN110831618A | 2020-02-21 |
Other References:
DATABASE Protein NCBI; 1 December 2020 (2020-12-01), ANONYMOUS : "Chain A, A. acutangulus PKS2", XP093035398, Database accession no. 6J1M_A
ROMEK KATARZYNA M., REMAUD GÉRALD S., SILVESTRE VIRGINIE, PANETH PIOTR, ROBINS RICHARD J.: "Non-statistical 13C Fractionation Distinguishes Co-incident and Divergent Steps in the Biosynthesis of the Alkaloids Nicotine and Tropine", JOURNAL OF BIOLOGICAL CHEMISTRY, AMERICAN SOCIETY FOR BIOCHEMISTRY AND MOLECULAR BIOLOGY, US, vol. 291, no. 32, 1 August 2016 (2016-08-01), US , pages 16620 - 16629, XP093035402, ISSN: 0021-9258, DOI: 10.1074/jbc.M116.734087
FRIESEN J. BRENT, EDWARD LEETE: "Nicotine synthase - an enzyme from nicotiana species which catalyzes the formation of (S)-nicotine from nicotinic acid and 1-methyl-δ'pyrrolinium chloride", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 31, no. 44, 1 January 1990 (1990-01-01), Amsterdam , NL , pages 6295 - 6298, XP093035406, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)97046-1
JAMIESON COOPER S., MISA JOSHUA, TANG YI, BILLINGSLEY JOHN M.: "Biosynthesis and synthetic biology of psychoactive natural products", CHEMICAL SOCIETY REVIEWS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 50, no. 12, 21 June 2021 (2021-06-21), UK , pages 6950 - 7008, XP093035409, ISSN: 0306-0012, DOI: 10.1039/D1CS00065A
ROMEK KATARZYNA M., REMAUD GÉRALD S., SILVESTRE VIRGINIE, PANETH PIOTR, ROBINS RICHARD J.: "Non-statistical 13C Fractionation Distinguishes Co-incident and Divergent Steps in the Biosynthesis of the Alkaloids Nicotine and Tropine", JOURNAL OF BIOLOGICAL CHEMISTRY, AMERICAN SOCIETY FOR BIOCHEMISTRY AND MOLECULAR BIOLOGY, US, vol. 291, no. 32, 1 August 2016 (2016-08-01), US , pages 16620 - 16629, XP093035402, ISSN: 0021-9258, DOI: 10.1074/jbc.M116.734087
FRIESEN J. BRENT, EDWARD LEETE: "Nicotine synthase - an enzyme from nicotiana species which catalyzes the formation of (S)-nicotine from nicotinic acid and 1-methyl-δ'pyrrolinium chloride", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 31, no. 44, 1 January 1990 (1990-01-01), Amsterdam , NL , pages 6295 - 6298, XP093035406, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)97046-1
JAMIESON COOPER S., MISA JOSHUA, TANG YI, BILLINGSLEY JOHN M.: "Biosynthesis and synthetic biology of psychoactive natural products", CHEMICAL SOCIETY REVIEWS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 50, no. 12, 21 June 2021 (2021-06-21), UK , pages 6950 - 7008, XP093035409, ISSN: 0306-0012, DOI: 10.1039/D1CS00065A
Attorney, Agent or Firm:
SHENPAT INTELLECTUAL PROPERTY AGENCY (CN)
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