Title:
EFFICIENT METHOD FOR PRODUCING AMBREIN
Document Type and Number:
WIPO Patent Application WO/2019/045058
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide a method for producing ambrein capable of obtaining ambrein easily and efficiently. This problem can be solved by a mutant tetraprenyl-β-curcumene cyclase of the present invention in which (1) the aspartic acid which is the fourth amino acid residue of the DXDD motif is substituted by an amino acid other than aspartic acid and (2) the amino acid adjacent to the N end of the (A/S/G)RX(H/N)XXP motif is substituted by an amino acid other than tyrosine, or the fourth amino acid of the GXGX(G/A/P) motif is substituted by an amino acid other than tyrosine.
Inventors:
SATO TSUTOMU (JP)
HOSHINO TSUTOMU (JP)
TAKEHANA TOSHIHIKO (JP)
KOIKE SEIJI (JP)
SHIGENO KOICHI (JP)
HOSHINO TSUTOMU (JP)
TAKEHANA TOSHIHIKO (JP)
KOIKE SEIJI (JP)
SHIGENO KOICHI (JP)
Application Number:
PCT/JP2018/032418
Publication Date:
March 07, 2019
Filing Date:
August 31, 2018
Export Citation:
Assignee:
UNIV NIIGATA (JP)
ADEKA CORP (JP)
ADEKA CORP (JP)
International Classes:
C12N15/61; C12N1/15; C12N1/19; C12N1/21; C12N9/90; C12P7/02
Domestic Patent References:
| WO2015033746A1 | 2015-03-12 | |||
| WO2015033746A1 | 2015-03-12 |
Foreign References:
| JPH10236996A | 1998-09-08 | |||
| JPS58110600A | 1983-07-01 | |||
| US4686191A | 1987-08-11 | |||
| US4939094A | 1990-07-03 | |||
| US5160735A | 1992-11-03 | |||
| JPS63233798A | 1988-09-29 |
Other References:
UEDA, DAIJIRO ET AL.: "4P-F198: Creation of squalene-ambrein cyclase: ambrein can be synthesized from squalene by one enzyme through two pathways", ABSTRACTS OF THE 69TH ANNUAL MEETING OF THE BIOTECHNOLOGY SOCIETY OF JAPAN; 11-14/09/2017, vol. 69, 8 August 2017 (2017-08-08), Japan, pages 321, XP009519160
MURAKAMI, MIZUKI ET AL.: "3C11p11 Analysis of catalytic mechanism of bifunctional triterpene / sesquarterpene cyclase", 2017 ANNUAL MEETING OF THE JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY, AND AGROCHEMISTRY (JSBBA); 17-20/03/2017, 5 March 2017 (2017-03-05), JAPAN, pages 1144, XP009519159, ISSN: 2186-7976
SATO, T. ET AL.: "Functional analysis of the DXDDTA motif in squalene-hopene cyclase by site- directed mutagenesis experiments: initiation site of the polycyclization reaction and stabilization site of the carbocation intermediate of the initially cyclized A-ring, Biosci", BIOTECHNOL. BIOCHEM., vol. 63, no. 12, December 1999 (1999-12-01), pages 2189 - 2198, XP055325754, DOI: 10.1271/bbb.63.2189
SATO, T. ET AL.: "Catalytic function of the residues of phenylalanine and tyrosine conserved in squalene-hopene cyclases", BIOSCI. BIOTECHNOL. BIOCHEM., vol. 65, no. 10, October 2001 (2001-10-01), pages 2233 - 2242, XP055325755, DOI: 10.1271/bbb.65.2233
UEDA, D. ET AL.: "Cyclization of squalene from both termini: identification of an onoceroid synthesis and enzymatic synthesis of ambrein", J. AM. CHEM. SOC., vol. 135, no. 49, 11 December 2013 (2013-12-11), pages 18335 - 18338, XP055325753, DOI: 10.1021/ja4107226
TETRAHEDRON ASYMMETRY, vol. 17, 2006, pages 30373rd045
BIOSCI. BIOTECHNOL. BIOCHEM., vol. 63, 1999, pages 2189 - 2198
BIOSCI. BIOTECHNOL. BIOCHEM., vol. 65, 2001, pages 2233 - 2242
BIOSCI. BIOTECHNOL. BIOCHEM., vol. 66, 2002, pages 1660 - 167
J. AM. CHEM. SOC., vol. 133, 2011, pages 17540 - 17543
J. AM. CHEM. SOC., vol. 135, 2013, pages 18335 - 18338
AGRICULTURAL BIOLOGICAL CHEMISTRY, vol. 48, 1984, pages 669
AGRIC. BIOL. CHEM., vol. 53, 1989, pages 277
PROC. NATL. ACAD. SCI. USA, vol. 82, 1985, pages 4306
GENE, vol. 33, 1985, pages 103
J. BACTERIOL., vol. 172, 1990, pages 2392
MURAKAMI, MIZUKI ET AL.: "3C11p11 Analysis of catalytic mechanism of bifunctional triterpene / sesquarterpene cyclase", 2017 ANNUAL MEETING OF THE JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY, AND AGROCHEMISTRY (JSBBA); 17-20/03/2017, 5 March 2017 (2017-03-05), JAPAN, pages 1144, XP009519159, ISSN: 2186-7976
SATO, T. ET AL.: "Functional analysis of the DXDDTA motif in squalene-hopene cyclase by site- directed mutagenesis experiments: initiation site of the polycyclization reaction and stabilization site of the carbocation intermediate of the initially cyclized A-ring, Biosci", BIOTECHNOL. BIOCHEM., vol. 63, no. 12, December 1999 (1999-12-01), pages 2189 - 2198, XP055325754, DOI: 10.1271/bbb.63.2189
SATO, T. ET AL.: "Catalytic function of the residues of phenylalanine and tyrosine conserved in squalene-hopene cyclases", BIOSCI. BIOTECHNOL. BIOCHEM., vol. 65, no. 10, October 2001 (2001-10-01), pages 2233 - 2242, XP055325755, DOI: 10.1271/bbb.65.2233
UEDA, D. ET AL.: "Cyclization of squalene from both termini: identification of an onoceroid synthesis and enzymatic synthesis of ambrein", J. AM. CHEM. SOC., vol. 135, no. 49, 11 December 2013 (2013-12-11), pages 18335 - 18338, XP055325753, DOI: 10.1021/ja4107226
TETRAHEDRON ASYMMETRY, vol. 17, 2006, pages 30373rd045
BIOSCI. BIOTECHNOL. BIOCHEM., vol. 63, 1999, pages 2189 - 2198
BIOSCI. BIOTECHNOL. BIOCHEM., vol. 65, 2001, pages 2233 - 2242
BIOSCI. BIOTECHNOL. BIOCHEM., vol. 66, 2002, pages 1660 - 167
J. AM. CHEM. SOC., vol. 133, 2011, pages 17540 - 17543
J. AM. CHEM. SOC., vol. 135, 2013, pages 18335 - 18338
AGRICULTURAL BIOLOGICAL CHEMISTRY, vol. 48, 1984, pages 669
AGRIC. BIOL. CHEM., vol. 53, 1989, pages 277
PROC. NATL. ACAD. SCI. USA, vol. 82, 1985, pages 4306
GENE, vol. 33, 1985, pages 103
J. BACTERIOL., vol. 172, 1990, pages 2392
Attorney, Agent or Firm:
YAMAGUCHI Kenjiro et al. (JP)
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