Title:
PYRROLOQUINOLINE QUINONE ALCOHOL ADDUCT
Document Type and Number:
WIPO Patent Application WO/2013/051414
Kind Code:
A1
Abstract:
The present invention pertains to: compounds represented by formula (A) or (B), which enable the red color of pyrroloquinoline quinine (PQQ) to be improved and enable the original functions of PQQ to be obtained, and salts thereof; and a method for efficiently producing said compounds. (In the formula, R is an alkyl group, a hydroxyalkyl group, a dihydroxyalkyl group, or an alkoxyalkyl group.)
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Inventors:
IKEMOTO KAZUTO (JP)
SAKAMOTO HITOSHI (JP)
SAKAMOTO HITOSHI (JP)
Application Number:
PCT/JP2012/074411
Publication Date:
April 11, 2013
Filing Date:
September 24, 2012
Export Citation:
Assignee:
MITSUBISHI GAS CHEMICAL CO (JP)
International Classes:
C07D471/04; A23L1/30; A23L2/52; A61K8/49; A61Q5/00; A61Q19/00; A61K31/4745; A61P31/04; A61P43/00
Foreign References:
| JPH0570459A | 1993-03-23 | |||
| US20110152526A1 | 2011-06-23 |
Other References:
DEKKER, ROBERT H. ET AL.: "Covalent addition of water, enzyme substrates and activators to pyrrolo-quinoline quinone, the coenzyme of quinoproteins", EUROPEAN JOURNAL OF BIOCHEMISTRY, vol. 125, no. 1, 1982, pages 69 - 73, XP055211857
JOHANNES FRANK JZN ET AL.: "Kinetic and spectral studies on the redox forms of methanol dehydrogenase from Hyphomicrobium X", EUROPEAN JOURNAL OF BIOCHEMISTRY, vol. 174, no. 2, June 1988 (1988-06-01), pages 331 - 338
ANDRES, J. ET AL.: "Quantum chemical studies of pyrroloquinoline quinone: PM3 pathways for methanol oxidation", BIOORGANIC CHEMISTRY, vol. 22, no. 1, March 1994 (1994-03-01), pages 58 - 71, XP024023093, DOI: doi:10.1006/bioo.1994.1005
ITOH, SHINOBU ET AL.: "C-4 and C-5 adducts of cofactor PQQ (pyrroloquinolinequinone). Model studies directed toward the action of quinoprotein methanol dehydrogenase", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 115, no. 22, 1993, pages 9960 - 7, XP002625971
PIRRUNG, MICHAEL C.: "Modeling of the chemistry of quinoprotein methanol dehydrogenase. Oxidation of methanol by calcium complex of coenzyme PQQ via addition-elimination mechanism", CHEMTRACTS, vol. 10, no. 11, October 1997 (1997-10-01), pages 828 - 830
SAITO, SHIZUKA ET AL.: "Quinone hemiacetal formation from protocatechuic acid during the DPPH radical scavenging reaction", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 67, no. 7, 8 August 2003 (2003-08-08), pages 1578 - 1579
JOHANNES FRANK JZN ET AL.: "Kinetic and spectral studies on the redox forms of methanol dehydrogenase from Hyphomicrobium X", EUROPEAN JOURNAL OF BIOCHEMISTRY, vol. 174, no. 2, June 1988 (1988-06-01), pages 331 - 338
ANDRES, J. ET AL.: "Quantum chemical studies of pyrroloquinoline quinone: PM3 pathways for methanol oxidation", BIOORGANIC CHEMISTRY, vol. 22, no. 1, March 1994 (1994-03-01), pages 58 - 71, XP024023093, DOI: doi:10.1006/bioo.1994.1005
ITOH, SHINOBU ET AL.: "C-4 and C-5 adducts of cofactor PQQ (pyrroloquinolinequinone). Model studies directed toward the action of quinoprotein methanol dehydrogenase", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 115, no. 22, 1993, pages 9960 - 7, XP002625971
PIRRUNG, MICHAEL C.: "Modeling of the chemistry of quinoprotein methanol dehydrogenase. Oxidation of methanol by calcium complex of coenzyme PQQ via addition-elimination mechanism", CHEMTRACTS, vol. 10, no. 11, October 1997 (1997-10-01), pages 828 - 830
SAITO, SHIZUKA ET AL.: "Quinone hemiacetal formation from protocatechuic acid during the DPPH radical scavenging reaction", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 67, no. 7, 8 August 2003 (2003-08-08), pages 1578 - 1579
Attorney, Agent or Firm:
INABA, Yoshiyuki et al. (JP)
Yoshiyuki Inaba (JP)
Yoshiyuki Inaba (JP)
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