Title:
PROCESS FOR PRODUCTION OF (R)-3-QUINUCLIDINOL
Document Type and Number:
WIPO Patent Application WO/2010/123062
Kind Code:
A1
Abstract:
Disclosed is a process for producing (R)-3-quinuclidinol, which is a compound useful as an intermediate for the production of pharmaceutical agents, effectively and on an industrial scale.
(R)-3-Quinuclidinol can be produced by reacting a polypeptide derived from a bacterium belonging to the genus Burkholderia or a transgenic organism imparted with an ability of producing the polypeptide with 3-quinuclidinone or a salt thereof to reduce 3-quinuclidinone or the salt thereof.
Inventors:
KAWANO SHIGERU (JP)
NISHIHACHIJYO MASAKATSU (JP)
YASOHARA YOSHIHIKO (JP)
ONODERA KEIKO (JP)
NISHIHACHIJYO MASAKATSU (JP)
YASOHARA YOSHIHIKO (JP)
ONODERA KEIKO (JP)
Application Number:
PCT/JP2010/057139
Publication Date:
October 28, 2010
Filing Date:
April 22, 2010
Export Citation:
Assignee:
KANEKA CORP (JP)
NAT UNIV CORP NARA INST (JP)
KAWANO SHIGERU (JP)
NISHIHACHIJYO MASAKATSU (JP)
YASOHARA YOSHIHIKO (JP)
ONODERA KEIKO (JP)
NAT UNIV CORP NARA INST (JP)
KAWANO SHIGERU (JP)
NISHIHACHIJYO MASAKATSU (JP)
YASOHARA YOSHIHIKO (JP)
ONODERA KEIKO (JP)
International Classes:
C12P17/18; C12N15/09
Domestic Patent References:
| WO1994003613A1 | 1994-02-17 |
Foreign References:
| JPH10243795A | 1998-09-14 | |||
| JPH11196890A | 1999-07-27 | |||
| JP2002153293A | 2002-05-28 | |||
| JP2000245495A | 2000-09-12 | |||
| JP2003230398A | 2003-08-19 | |||
| JP2003334069A | 2003-11-25 | |||
| JP2007124922A | 2007-05-24 |
Other References:
YAMADA-ONODERA, K. ET AL.: "Purification and characterization of 2-aminoacetophenone reductase of newly isolated Burkholderia sp.", YT. J BIOSCI BIOENG., vol. 104, no. 5, 2007, pages 416 - 419, XP022391309
DATABASE DDBJ/EMBL/GENBANK [online] 3 January 2009 (2009-01-03), COPELAND, A. ET AL.: "Definition: Short-chain dehydrogenase/reductase SDR [Burkholderia sp. 383].", XP008163992, Database accession no. YP_371686
DATABASE DDBJ/EMBL/GENBANK [online] 29 July 2008 (2008-07-29), OHTSUBO, Y. ET AL.: "Definition: 3-oxoacyl-[acyl-carrier protein] reductase [Burkholderia multivorans ATCC 17616].", retrieved from http://www.ncbi.nlm.nih.gov/ sviewer/viewer.fcgi?val=189353458&sat=NCBI& satkey=23434573 Database accession no. YP_001949085
UZURA, A. ET AL.: "Stereoselective synthesis of (R)-3-quinuclidinol through asymmetric reduction of 3-quinuclidinone with 3-quinuclidinone reductase of Rhodotorula rubra.", APPL MICROBIOL BIOTECHNOL., vol. 83, 2009, pages 617 - 626, XP019705546
BROCK, A. ET AL.: "The functional divergence of short-chain dehydrogenases involved in tropinone reduction.", PLANT J., vol. 54, 2008, pages 388 - 401, XP055068528
NAITO, R. ET AL.: "Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4- tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists.", J MED CHEM., vol. 48, 2005, pages 6597 - 6606, XP002435582
See also references of EP 2423320A4
YAMADA-ONODERA K. ET AL., JOURNAL OF BIOSCIENCE AND BIOENGINEERING, vol. 014, no. 5, 2007, pages 416 - 419
"Current Protocols in Molecular Biology", 1989, JOHN WILEY AND SONS, INC.
"Molecular Cloning", 1989, COLD SPRING HARBOR LABORATORY PRESS
VISSER ET AL., APPL. MICROBIOL. BIOTECHNOL., vol. 53, 2000, pages 415
NUCL. ACIDS RES., vol. 16, 1988, pages 8186
"Molecular Cloning, A laboratory manual", 1989, COLD SPRING HARBOR LABORATORY PRESS
"Program Manual for The Wisconsin Package", September 1994, GENETICS COMPUTER GROUP
RICE, P.: "Program Manual for EGCG Package", 1996, THE SANGER CENTRE
"Biseibutsugaku Kiso Koza 8: Idensikogaku", KYORITSU SHUPPAN
NATURE, vol. 315, 1985, pages 592 - 594
J. MED. CHEM., vol. 48, 2005, pages 6597 - 6606
"Current Protocols in Molecular Biology", GREENE PUBLISHING ASSOCIATES AND WILEY-INTERSCIENCE
MURRAY ET AL., NUCL. ACIDS RES., vol. 8, 1980, pages 4321
EUR. J. BIOCHEM., vol. 186, 1989, pages 389
DATABASE DDBJ/EMBL/GENBANK [online] 3 January 2009 (2009-01-03), COPELAND, A. ET AL.: "Definition: Short-chain dehydrogenase/reductase SDR [Burkholderia sp. 383].", XP008163992, Database accession no. YP_371686
DATABASE DDBJ/EMBL/GENBANK [online] 29 July 2008 (2008-07-29), OHTSUBO, Y. ET AL.: "Definition: 3-oxoacyl-[acyl-carrier protein] reductase [Burkholderia multivorans ATCC 17616].", retrieved from http://www.ncbi.nlm.nih.gov/ sviewer/viewer.fcgi?val=189353458&sat=NCBI& satkey=23434573 Database accession no. YP_001949085
UZURA, A. ET AL.: "Stereoselective synthesis of (R)-3-quinuclidinol through asymmetric reduction of 3-quinuclidinone with 3-quinuclidinone reductase of Rhodotorula rubra.", APPL MICROBIOL BIOTECHNOL., vol. 83, 2009, pages 617 - 626, XP019705546
BROCK, A. ET AL.: "The functional divergence of short-chain dehydrogenases involved in tropinone reduction.", PLANT J., vol. 54, 2008, pages 388 - 401, XP055068528
NAITO, R. ET AL.: "Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4- tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists.", J MED CHEM., vol. 48, 2005, pages 6597 - 6606, XP002435582
See also references of EP 2423320A4
YAMADA-ONODERA K. ET AL., JOURNAL OF BIOSCIENCE AND BIOENGINEERING, vol. 014, no. 5, 2007, pages 416 - 419
"Current Protocols in Molecular Biology", 1989, JOHN WILEY AND SONS, INC.
"Molecular Cloning", 1989, COLD SPRING HARBOR LABORATORY PRESS
VISSER ET AL., APPL. MICROBIOL. BIOTECHNOL., vol. 53, 2000, pages 415
NUCL. ACIDS RES., vol. 16, 1988, pages 8186
"Molecular Cloning, A laboratory manual", 1989, COLD SPRING HARBOR LABORATORY PRESS
"Program Manual for The Wisconsin Package", September 1994, GENETICS COMPUTER GROUP
RICE, P.: "Program Manual for EGCG Package", 1996, THE SANGER CENTRE
"Biseibutsugaku Kiso Koza 8: Idensikogaku", KYORITSU SHUPPAN
NATURE, vol. 315, 1985, pages 592 - 594
J. MED. CHEM., vol. 48, 2005, pages 6597 - 6606
"Current Protocols in Molecular Biology", GREENE PUBLISHING ASSOCIATES AND WILEY-INTERSCIENCE
MURRAY ET AL., NUCL. ACIDS RES., vol. 8, 1980, pages 4321
EUR. J. BIOCHEM., vol. 186, 1989, pages 389
Attorney, Agent or Firm:
YASUTOMI & Associates (JP)
Patent business corporation Yasutomi international patent firm (JP)
Patent business corporation Yasutomi international patent firm (JP)
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