Title:
PROTEIN COMPLEX CAPABLE OF CATALYZING ASYMMETRIC OXIDATION REACTION AND METHOD FOR PRODUCING SAME
Document Type and Number:
WIPO Patent Application WO/2014/073673
Kind Code:
A1
Abstract:
Provided are: a protein complex capable of selectively and asymmetrically oxidizing one of enantiomers of a secondary alcohol without adding a coenzyme and having an asymmetric oxidation activity in a water-soluble solvent system in the presence of oxygen; a method for producing the same; and a production method relating to coating of the protein complex with a high molecular compound.
A method for producing a protein complex capable of catalyzing an asymmetric oxidation reaction, said method being characterized by comprising: a first step that comprises a treatment for enclosing a crude water-soluble protein derived from an animal or plant in a gel, a treatment for air-oxidizing the gel, and a treatment for eluting the protein complex from the gel into an aqueous solution; and a second step that comprises a treatment for applying gravity to the aqueous solution of the protein complex to concentrate and precipitate the protein complex, a treatment for re-dissolving the protein complex precipitate in an aqueous glycine sodium hydroxide solution of about 0.5 mM and allowing the same to homogeneously coexist with a high molecular compound, and a treatment for re-precipitating the coexistence solution and dehydrating and drying the same to give the protein complex coated with the high molecular compound.
Inventors:
NAGAOKA HIROYUKI (JP)
Application Number:
PCT/JP2013/080351
Publication Date:
May 15, 2014
Filing Date:
November 08, 2013
Export Citation:
Assignee:
SANYO FOODS CO LTD (JP)
International Classes:
C12P7/02; C12N9/02; C12P41/00
Domestic Patent References:
| WO2010134642A1 | 2010-11-25 | |||
| WO1999034010A1 | 1999-07-08 | |||
| WO2010134642A1 | 2010-11-25 |
Foreign References:
| JP2001019650A | 2001-01-23 | |||
| JP3294860B2 | 2002-06-24 | |||
| JP3683129B2 | 2005-08-17 |
Other References:
See also references of EP 2918683A4
SABURO FUKUI: "Bioreactor", article "Kagaku Zokan No. 119, Production of Useful Substances by Hybrid Process"
ICHIROU CHIBATA,: "Immobilized Enzyme", KODANSHA SCIENTIFIC LTD
CHEMISTRY AND INDUSTRY, vol. 62-1, January 2009 (2009-01-01), pages 44 - 45
D.S. AULD: "The role of zinc for alcohol dehydrogenase structure", CELL MOL. LIFE SCI., vol. 64, 2008, pages 3961 - 3970, XP019652193
AFOLABI: "Site-directed mutagenesis and X-ray crystallography of the PQQ-containing quinoprotein methanol dehydrogenase and its electron acceptor, cytochrome cL", BIOCHEMISTRY, vol. 40, 2001, pages 9799 - 9809
ZEE, J.M.: "Defects in cytochrome oxidase assembly in humans: Lessons from yeast.", BIOCHEM. CELL. BIOL., vol. 84, 2006, pages 859 - 869
HAYS PUTNAM: "Replacement of an electron transfer pathway in cytochrome c peroxidase with a surrogate peptide", BIOCHEMISTRY, vol. 48, 2009, pages 1 - 3
GOTOH: "Poly(ethylene glycol)-lipase complex that are highly active and enantioselective in ionic liquid", ORG. BIOMOL. CHEM., 2004, pages 1239 - 1244
FOOD AND TECHNOLOGY, December 2008 (2008-12-01), pages 1 - 9
"Protein, Nucleic acid, Enzyme", MOLECULAR DESIGN OF METALLOENZYME, MAINLY HEME ENZYME, vol. 49, no. 14, November 2004 (2004-11-01)
VINAY V. THAKUR: ""-Enantioselective synthesis of (S)-a-arylpropionic acid via Pd-catalyzed kinetic resolution of benzylic alcohols-",", .
STOIMENOVA, M: "Nitrite-driven anaerobic ATP synthesis in barley and rice root mitochondria", PLANTA, vol. 226, no. 2, July 2007 (2007-07-01), pages 465 - 74, XP019517521, DOI: doi:10.1007/s00425-007-0496-0
YOSHIKAZU ABE: "Remarkable Activation of an Enzyme by (R)-Pyrrolidine-Substituted Imidazolium Alkyl PEG Sulfate", ADV. SYNTH. CATAL., vol. 350, 2008, pages 1954 - 1958
HIDEHIKO HIRAKAWA: "Construction of Artificial Enzyme Complexes using Ring-Shaped Heterotrimeric Proteins, Construction of Self-Sufficient Cytochrome P450", CHEMISTRY AND BIOLOGY, vol. 51, no. 8, 2013, pages 521 - 523
F.P. GUENGERICH: "For more information on cytochrome P450 from a genomics perspective", CHEM. RES. TOXICOL., vol. 14, 2001, pages 611 - 650
KOJI MIYAMOTO: "Biosynthesis Gene Cluster of Defense Response Substances Acquired by Plants, Control Mechanism of Phytoalexin Production in Rice", CHEMISTRY AND BIOLOGY, vol. 51, no. 5, 2013, pages 310 - 317
SYLVIE LETOFFE: "Functional Characterization of the HasAPF Hemophore and its Truncated and Chimeric Variants: Determination of a Region involved in Binding to the Hemophore Receptor", J. BACTERIOL., vol. 182, no. 16, 2000, pages 4401 - 4405
STEFANIE KRIEG: "Heme uptake across the outer membrane as revealed by crystal structures of the receptor-hemophore complex", PNAS, vol. 106, no. 4, 2009, pages 1045 - 1050
"Hygienic Chemistry", vol. 24, 31 August 1978, PHARMACEUTICAL SOCIETY OF JAPAN, pages: 175 - 181
SABURO FUKUI: "Bioreactor", article "Kagaku Zokan No. 119, Production of Useful Substances by Hybrid Process"
ICHIROU CHIBATA,: "Immobilized Enzyme", KODANSHA SCIENTIFIC LTD
CHEMISTRY AND INDUSTRY, vol. 62-1, January 2009 (2009-01-01), pages 44 - 45
D.S. AULD: "The role of zinc for alcohol dehydrogenase structure", CELL MOL. LIFE SCI., vol. 64, 2008, pages 3961 - 3970, XP019652193
AFOLABI: "Site-directed mutagenesis and X-ray crystallography of the PQQ-containing quinoprotein methanol dehydrogenase and its electron acceptor, cytochrome cL", BIOCHEMISTRY, vol. 40, 2001, pages 9799 - 9809
ZEE, J.M.: "Defects in cytochrome oxidase assembly in humans: Lessons from yeast.", BIOCHEM. CELL. BIOL., vol. 84, 2006, pages 859 - 869
HAYS PUTNAM: "Replacement of an electron transfer pathway in cytochrome c peroxidase with a surrogate peptide", BIOCHEMISTRY, vol. 48, 2009, pages 1 - 3
GOTOH: "Poly(ethylene glycol)-lipase complex that are highly active and enantioselective in ionic liquid", ORG. BIOMOL. CHEM., 2004, pages 1239 - 1244
FOOD AND TECHNOLOGY, December 2008 (2008-12-01), pages 1 - 9
"Protein, Nucleic acid, Enzyme", MOLECULAR DESIGN OF METALLOENZYME, MAINLY HEME ENZYME, vol. 49, no. 14, November 2004 (2004-11-01)
VINAY V. THAKUR: ""-Enantioselective synthesis of (S)-a-arylpropionic acid via Pd-catalyzed kinetic resolution of benzylic alcohols-",", .
STOIMENOVA, M: "Nitrite-driven anaerobic ATP synthesis in barley and rice root mitochondria", PLANTA, vol. 226, no. 2, July 2007 (2007-07-01), pages 465 - 74, XP019517521, DOI: doi:10.1007/s00425-007-0496-0
YOSHIKAZU ABE: "Remarkable Activation of an Enzyme by (R)-Pyrrolidine-Substituted Imidazolium Alkyl PEG Sulfate", ADV. SYNTH. CATAL., vol. 350, 2008, pages 1954 - 1958
HIDEHIKO HIRAKAWA: "Construction of Artificial Enzyme Complexes using Ring-Shaped Heterotrimeric Proteins, Construction of Self-Sufficient Cytochrome P450", CHEMISTRY AND BIOLOGY, vol. 51, no. 8, 2013, pages 521 - 523
F.P. GUENGERICH: "For more information on cytochrome P450 from a genomics perspective", CHEM. RES. TOXICOL., vol. 14, 2001, pages 611 - 650
KOJI MIYAMOTO: "Biosynthesis Gene Cluster of Defense Response Substances Acquired by Plants, Control Mechanism of Phytoalexin Production in Rice", CHEMISTRY AND BIOLOGY, vol. 51, no. 5, 2013, pages 310 - 317
SYLVIE LETOFFE: "Functional Characterization of the HasAPF Hemophore and its Truncated and Chimeric Variants: Determination of a Region involved in Binding to the Hemophore Receptor", J. BACTERIOL., vol. 182, no. 16, 2000, pages 4401 - 4405
STEFANIE KRIEG: "Heme uptake across the outer membrane as revealed by crystal structures of the receptor-hemophore complex", PNAS, vol. 106, no. 4, 2009, pages 1045 - 1050
"Hygienic Chemistry", vol. 24, 31 August 1978, PHARMACEUTICAL SOCIETY OF JAPAN, pages: 175 - 181
Attorney, Agent or Firm:
ISHIDA, Takashi et al. (JP)
Ishida 敬 (JP)
Ishida 敬 (JP)
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