CHEMICAL BEHAVIOR OF COENZYME PQQ TOWARD AMINOGUANIDINE - REDOX REACTION AND ADDUCT FORMATION

被引:14
作者
MURE, M [1 ]
NII, K [1 ]
ITOH, S [1 ]
OHSHIRO, Y [1 ]
机构
[1] OSAKA UNIV, FAC ENGN, DEPT APPL CHEM, YAMADAOKA 2-1, SUITA, OSAKA 565, JAPAN
关键词
D O I
10.1246/bcsj.63.417
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of coenzyme PQQ with aminoguanidine, which is known as an inhibitor of quinoprotein amine oxidases, was investigated in vitro. The redox reaction predominantly proceeded at pH 10.0 to give PQQH2 (quinol), whereas deactivation of PQQ occurred at pH 6.7 to give the triazine adduct. In the case of semicarbazide or acetohydrazide as the substrate, azo adduct formation was mainly observed even at pH 10.0. Importance of the C-5 carbinolamine-type intermediate a is discussed.
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页码:417 / 420
页数:4
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共 12 条
  • [1] MICROBIAL-PRODUCTION OF PYRROLOQUINOLINE QUINONE
    AMEYAMA, M
    HAYASHI, M
    MATSUSHITA, K
    SHINAGAWA, E
    ADACHI, O
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1984, 48 (02): : 561 - 565
  • [2] INHIBITION OF PLANT AND MAMMALIAN DIAMINE OXIDASES BY HYDRAZINE AND GUANIDINE COMPOUNDS
    BIEGANSKI, T
    OSINSKA, Z
    MASLINSKI, C
    [J]. INTERNATIONAL JOURNAL OF BIOCHEMISTRY, 1982, 14 (10): : 949 - 953
  • [3] COREY EJ, 1981, J AM CHEM SOC, V103, P5599, DOI 10.1021/ja00408a067
  • [4] COVALENT ADDITION OF H2O, ENZYME SUBSTRATES AND ACTIVATORS TO PYRROLO-QUINOLINE QUINONE, THE CO-ENZYME OF QUINOPROTEINS
    DEKKER, RH
    DUINE, JA
    FRANK, J
    EUGENE, JP
    VERWIEL, J
    WESTERLING, J
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1982, 125 (01): : 69 - 73
  • [5] REACTION OF REDUCED PQQ (PQQH2) AND MOLECULAR-OXYGEN
    ITOH, S
    OHSHIRO, Y
    AGAWA, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (06) : 1911 - 1914
  • [6] KINETICS AND MECHANISM OF THE OXIDATIVE DEAMINATION OF AMINES BY COENZYME PQQ
    ITOH, S
    KITAMURA, Y
    OHSHIRO, Y
    AGAWA, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (06) : 1907 - 1910
  • [7] HMO CONSIDERATION OF FACTORS AFFECTING TAUTOMERISM IN HYDROXYARYLAZO COMPOUNDS
    KUDER, JE
    [J]. TETRAHEDRON, 1972, 28 (07) : 1973 - &
  • [8] BOVINE SERUM AMINE OXIDASE - A MAMMALIAN ENZYME HAVING COVALENTLY BOUND PQQ AS PROSTHETIC GROUP
    LOBENSTEINVERBEEK, CL
    JONGEJAN, JA
    FRANK, J
    DUINE, JA
    [J]. FEBS LETTERS, 1984, 170 (02) : 305 - 309
  • [9] NEUNHOEFFER H, 1984, COMPREHENSIVE HETERO, P395
  • [10] PETTERSON G, 1982, STRUCTURE FUNCTIONS