Title:
PHENYLPYRUVATE REDUCTASE AND METHOD FOR MANUFACTURING OPTICALLY-ACTIVE PHENYLLACTIC ACID AND 4-HYDROXYL-PHENYLLACTIC ACID USING SAME ENZYME
Document Type and Number:
WIPO Patent Application WO/2012/105495
Kind Code:
A1
Abstract:
The present invention provides a phenylpyruvate reductase by which highly-pure optically-active 3-phenyllactic acid and highly-pure 4-hydroxyl-phenyllactic acid can be efficiently obtained, a gene coding for the same, and a method for manufacturing optically-active 3-phenyllactic acid and 4-hydroxyl-phenyllactic acid using the reductase and gene.
Inventors:
KONISHI KAZUNOBU (JP)
TAKAYA NAOKI (JP)
TAKAYA NAOKI (JP)
Application Number:
PCT/JP2012/051989
Publication Date:
August 09, 2012
Filing Date:
January 30, 2012
Export Citation:
Assignee:
ASAHI KASEI CHEMICALS CORP (JP)
KONISHI KAZUNOBU (JP)
TAKAYA NAOKI (JP)
KONISHI KAZUNOBU (JP)
TAKAYA NAOKI (JP)
International Classes:
C12N15/09; A23L29/00; C12N1/15; C12N1/19; C12N1/21; C12N5/10; C12P7/56; C12N9/02
Foreign References:
| JP2003192633A | 2003-07-09 | |||
| JPH0937792A | 1997-02-10 | |||
| JP2000300284A | 2000-10-31 | |||
| JP2001081563A | 2001-03-27 | |||
| JPH05344881A | 1993-12-27 | |||
| JP2006311833A | 2006-11-16 | |||
| JP2007325592A | 2007-12-20 | |||
| JPH05344811A | 1993-12-27 | |||
| US4681852A | 1987-07-21 |
Other References:
BODE R. ET AL.: "Purification and Properties of D-Aromatic Lactate Dehydrogenase: An Enzyme Involved in the Catabolism of the Aromatic Amino Acids of Candida maltosa", BIOCHEM. PHYSIOL. PFLANZEN, vol. 181, 1986, pages 189 - 198, XP009063426
RINTALA E. ET AL.: "The ORF YNL274c (GOR1) codes for glyoxylate reductase in Saccharomyces cerevisiae", YEAST, vol. 24, no. 2, February 2007 (2007-02-01), pages 129 - 136, XP009167436
HYMAN B.C. ET AL.: "Resolution of mitochondrial DNA structures in the large yeast Wickerhamia fluorescens", EXP. CELL RES., vol. 141, no. 1, 1982, pages 221 - 230, XP024856977
FUJII T. ET AL.: "Novel fungal phenylpyruvate reductase belongs to d-isomer-specific 2-hydroxyacid dehydrogenase family", BIOCHIM. BIOPHYS. ACTA, vol. 1814, no. 12, December 2011 (2011-12-01), pages 1669 - 1676, XP028121025
TAKASHI ITO ET AL.: "Development of D- phenyllactic acid-producing Escherichia coli using molecular breeding", DAI 63 KAI ABSTRACTS OF THE ANNUAL MEETING OF THE SOCIETY FOR BIOTECHNOLOGY, 25 August 2011 (2011-08-25), JAPAN, pages 152 - 2FA15
LAVERMICOCCA, P.; VALERIO, F.; EVIDENTE, A.; LAZZARONI, S.; CORSETTI, A.; GOBETTI, M., APPL. ENVIRON. MICROBIOL., vol. 66, 2000, pages 4084 - 4090
DIEULEVEUX, V.; VAN DER PYL, D.; CHATAUD, J.; GUEGUEN, M., APPL. ENVIRON. MICROBIOL., vol. 64, 1998, pages 800 - 803
PAOLA LA ET AL.: "Purification and characterization of novel antifungal compounds from the sourdough Lactobacillus plantarum strain 21B", APPLIED ENVIRONMENTAL MICROBIOLOGY, vol. 66, no. 9, 2000, pages 4084 - 4090
WANMENG MU ET AL.: "Production of 4-hydroxyphenyllactic acid by Lactobacillus sp. SK007", FERMENTATION JOURNAL OF BIOSCIENCE AND BIOENGINEERING, vol. 109, no. 4, 2010, pages 369 - 371, XP026949554, DOI: doi:10.1016/j.jbiosc.2009.10.005
OHHIRA, I.; KUWAKI, S.; MORITA, H.; SUZUKI, T.; TOMITA, S.; HISAMATSU, S.; SONOKI, S.; SHINODA, S., BIOCONTROL SCI., vol. 9, 2004, pages 77 - 81
DIEULEVEUX, V.; GUEGUEN, M., J. FOOD PROT., vol. 61, 1998, pages 1281 - 1285
DIEULEVEUX, V.; LEMARINIER, S.; GUEGUEN, M., INT. J. FOOD MICROBIOL., vol. 40, 1998, pages 177 - 183
STROM, K.; SJOGREN, J.; BROBERG, A.; SCHNURER, APPL. ENVIRON. MICROBIOL., vol. 68, 2002, pages 4322 - 4327
MAGNUSSON, J.; STROM, K.; ROOS, S.; SJOGREN, J.; SCHNURER, MICROBIOL. LETT., vol. 219, 2003, pages 129 - 135
VALERIO, F.; LAVERMICOCCA, P.; PASCALE, M.; VISCONTI, A., MICROBIOL. LETT., vol. 233, 2004, pages 289 - 295
LI, X.; PAN; MU, W.; ZHANG, T., JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 56, no. 7, 2008, pages 2392 - 399
JIANGHUA, J.; WANMENG, M.; TAO, Z.; BO., APPL. BIOCHEM. BIOTECHNOL., 2009
ISHIKURA, Y.; TSUZUKI, S.; TAKAHASHI, 0.; TOKUDA, C.; NAKANISHI, R.; SHINODA, T.; TAGUCHI, H., J. BIOCHEM., vol. 138, 2005, pages 741 - 749
EDMAN, P., ACTA CHEM. SCAND., vol. 4, 1950, pages 283 - 293
SHIMIZU, M. ET AL., PROTEOMICS, vol. 9, 2009, pages 7 - 19
SCIENCE, vol. 227, 1985, pages 1435
PROC. NATL. ACAD. SCI. USA, vol. 74, 1974, pages 5463
SAMBROOK ET AL.: "Molecular Cloning: A Laboratory Manual", 1989
SAMBROOK, J.; FRITCH, E. F.; MANIATIS, T.: "Molecular Cloning: A Laboratory Manual", vol. 2, 1989, COLD SPRING HARBOR LABORATORY PRESS
"PCR Technology", 1989, STOCKTON PRESS
KRAMER, W.; FRITS, H., J. METHODS IN ENZYMOLOGY, vol. 154, 1987, pages 350
GENE, vol. 77, 1987, pages 61
ALTSCHUL, S. F. ET AL., J. MOL. BIOL., vol. 215, 1990, pages 403 - 410
KURTZMAN, C. P.; FELL, J. W.: "The Yeasts: A Taxonomic Study", ELSEVIER
WHITAKER, R. J. ET AL., J. BIOL. CHEM., vol. 257, 1982, pages 3550 - 3556
J. BIOCHEM., vol. 138, 2005, pages 741 - 74915
LI, X. ET AL., BIOTECHNOL. LETT., vol. 29, 2007, pages 593 - 597
VERMUELEN, N. ET AL., J. AGRIC. FOOD CHEM., vol. 54, 2006, pages 3832 - 3839
TAGUCHI, H.; OHTA, T., J. BIOL. CHEM., vol. 266, 1991, pages 12588 - 12594
FAUVART, M. ET AL., BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1774, 2007, pages 1092 - 1098
BOOTH, M. P. ET AL., J. MOL. BIOL., vol. 360, 2006, pages 178 - 189
VALERIO, F. ET AL., FEMS MICROBIOL. LETTERS, vol. 233, 2004, pages 289 - 295
TSUJI, H. ET AL., J. APPL. POLYMER SCI., vol. 110, 2008, pages 3954 - 3962
YIN, M.; BAKER, G. L., MACROMOLECULES, vol. 32, 1999, pages 7711
See also references of EP 2674490A4
RINTALA E. ET AL.: "The ORF YNL274c (GOR1) codes for glyoxylate reductase in Saccharomyces cerevisiae", YEAST, vol. 24, no. 2, February 2007 (2007-02-01), pages 129 - 136, XP009167436
HYMAN B.C. ET AL.: "Resolution of mitochondrial DNA structures in the large yeast Wickerhamia fluorescens", EXP. CELL RES., vol. 141, no. 1, 1982, pages 221 - 230, XP024856977
FUJII T. ET AL.: "Novel fungal phenylpyruvate reductase belongs to d-isomer-specific 2-hydroxyacid dehydrogenase family", BIOCHIM. BIOPHYS. ACTA, vol. 1814, no. 12, December 2011 (2011-12-01), pages 1669 - 1676, XP028121025
TAKASHI ITO ET AL.: "Development of D- phenyllactic acid-producing Escherichia coli using molecular breeding", DAI 63 KAI ABSTRACTS OF THE ANNUAL MEETING OF THE SOCIETY FOR BIOTECHNOLOGY, 25 August 2011 (2011-08-25), JAPAN, pages 152 - 2FA15
LAVERMICOCCA, P.; VALERIO, F.; EVIDENTE, A.; LAZZARONI, S.; CORSETTI, A.; GOBETTI, M., APPL. ENVIRON. MICROBIOL., vol. 66, 2000, pages 4084 - 4090
DIEULEVEUX, V.; VAN DER PYL, D.; CHATAUD, J.; GUEGUEN, M., APPL. ENVIRON. MICROBIOL., vol. 64, 1998, pages 800 - 803
PAOLA LA ET AL.: "Purification and characterization of novel antifungal compounds from the sourdough Lactobacillus plantarum strain 21B", APPLIED ENVIRONMENTAL MICROBIOLOGY, vol. 66, no. 9, 2000, pages 4084 - 4090
WANMENG MU ET AL.: "Production of 4-hydroxyphenyllactic acid by Lactobacillus sp. SK007", FERMENTATION JOURNAL OF BIOSCIENCE AND BIOENGINEERING, vol. 109, no. 4, 2010, pages 369 - 371, XP026949554, DOI: doi:10.1016/j.jbiosc.2009.10.005
OHHIRA, I.; KUWAKI, S.; MORITA, H.; SUZUKI, T.; TOMITA, S.; HISAMATSU, S.; SONOKI, S.; SHINODA, S., BIOCONTROL SCI., vol. 9, 2004, pages 77 - 81
DIEULEVEUX, V.; GUEGUEN, M., J. FOOD PROT., vol. 61, 1998, pages 1281 - 1285
DIEULEVEUX, V.; LEMARINIER, S.; GUEGUEN, M., INT. J. FOOD MICROBIOL., vol. 40, 1998, pages 177 - 183
STROM, K.; SJOGREN, J.; BROBERG, A.; SCHNURER, APPL. ENVIRON. MICROBIOL., vol. 68, 2002, pages 4322 - 4327
MAGNUSSON, J.; STROM, K.; ROOS, S.; SJOGREN, J.; SCHNURER, MICROBIOL. LETT., vol. 219, 2003, pages 129 - 135
VALERIO, F.; LAVERMICOCCA, P.; PASCALE, M.; VISCONTI, A., MICROBIOL. LETT., vol. 233, 2004, pages 289 - 295
LI, X.; PAN; MU, W.; ZHANG, T., JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 56, no. 7, 2008, pages 2392 - 399
JIANGHUA, J.; WANMENG, M.; TAO, Z.; BO., APPL. BIOCHEM. BIOTECHNOL., 2009
ISHIKURA, Y.; TSUZUKI, S.; TAKAHASHI, 0.; TOKUDA, C.; NAKANISHI, R.; SHINODA, T.; TAGUCHI, H., J. BIOCHEM., vol. 138, 2005, pages 741 - 749
EDMAN, P., ACTA CHEM. SCAND., vol. 4, 1950, pages 283 - 293
SHIMIZU, M. ET AL., PROTEOMICS, vol. 9, 2009, pages 7 - 19
SCIENCE, vol. 227, 1985, pages 1435
PROC. NATL. ACAD. SCI. USA, vol. 74, 1974, pages 5463
SAMBROOK ET AL.: "Molecular Cloning: A Laboratory Manual", 1989
SAMBROOK, J.; FRITCH, E. F.; MANIATIS, T.: "Molecular Cloning: A Laboratory Manual", vol. 2, 1989, COLD SPRING HARBOR LABORATORY PRESS
"PCR Technology", 1989, STOCKTON PRESS
KRAMER, W.; FRITS, H., J. METHODS IN ENZYMOLOGY, vol. 154, 1987, pages 350
GENE, vol. 77, 1987, pages 61
ALTSCHUL, S. F. ET AL., J. MOL. BIOL., vol. 215, 1990, pages 403 - 410
KURTZMAN, C. P.; FELL, J. W.: "The Yeasts: A Taxonomic Study", ELSEVIER
WHITAKER, R. J. ET AL., J. BIOL. CHEM., vol. 257, 1982, pages 3550 - 3556
J. BIOCHEM., vol. 138, 2005, pages 741 - 74915
LI, X. ET AL., BIOTECHNOL. LETT., vol. 29, 2007, pages 593 - 597
VERMUELEN, N. ET AL., J. AGRIC. FOOD CHEM., vol. 54, 2006, pages 3832 - 3839
TAGUCHI, H.; OHTA, T., J. BIOL. CHEM., vol. 266, 1991, pages 12588 - 12594
FAUVART, M. ET AL., BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1774, 2007, pages 1092 - 1098
BOOTH, M. P. ET AL., J. MOL. BIOL., vol. 360, 2006, pages 178 - 189
VALERIO, F. ET AL., FEMS MICROBIOL. LETTERS, vol. 233, 2004, pages 289 - 295
TSUJI, H. ET AL., J. APPL. POLYMER SCI., vol. 110, 2008, pages 3954 - 3962
YIN, M.; BAKER, G. L., MACROMOLECULES, vol. 32, 1999, pages 7711
See also references of EP 2674490A4
Attorney, Agent or Firm:
IWASE Yoshikazu et al. (JP)
Iwase Yoshiwa (JP)
Iwase Yoshiwa (JP)
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