Pyrroloquinoline Quinone: A Novel Cofactor
Tài liệu tham khảo
Ameyama, 1981, Existence of a novel prosthetic group, PQQ, in membrane-bound, electron transport chain-linked, primary dehydrogenase of oxidative bacteria, FEBS Lett., 130, 179, 10.1016/0014-5793(81)81114-3
Ameyama, 1984, Growth stimulation of microorganisms by pyrroloquinoline quinone, Agric. Biol. Chem., 48, 2909, 10.1271/bbb1961.48.2909
Ameyama, 1984, Growth stimulating substance for microorganisms produced by Escherichia coli causing the reduction of the lag phase in microbial growth and identity of the substance with pyrroloquinoline quinone, Agric. Biol. Chem., 48, 3099, 10.1271/bbb1961.48.3099
Ameyama, 1985, Growth stimulating activity for microorganisms in naturally occurring substances and partial characterization of the substance for the activity as pyrroloquinoline quinone, Agric. Biol. Chem., 49, 699, 10.1271/bbb1961.49.699
Ameyama, 1985, How many times should the inoculum be rinsed before inoculation in the assay for growth stimulating activity of pyrroloquinoline quinone?, Agric. Biol. Chem., 49, 853, 10.1271/bbb1961.49.853
Ameyama, 1985, Mode of binding of pyrroloquinoline quinone to apo-glucose dehydrogenase, Agric. Biol. Chem., 49, 1227, 10.1271/bbb1961.49.1227
Ameyama, 1985, Method of enzymatic determination of pyrroloquinoline quinone, Anal. Biochem., 151, 263, 10.1016/0003-2697(85)90174-5
Anthony, 1967, The microbial oxidation of methanol. The prosthetic group of the alcohol dehydrogenase of Pseudomonas spec. M27: A new oxidoreductase prosthetic group, Biochem. J., 104, 960, 10.1042/bj1040960
Bird, 1982, Lysyl oxidase: Evidence that pyridoxal phosphate is a cofactor, Biochem. Biophys. Res. Commun., 108, 1172, 10.1016/0006-291X(82)92124-6
Biville, 1988, Physiological properties of a pyrroloquinoline quinone mutant of Methylobacterium organophilum, FEMS Microbiol. Lett., 52, 53, 10.1111/j.1574-6968.1988.tb02571.x
Buechi, 1985, A synthesis of methoxatin, J. Am. Chem. Soc., 107, 5555, 10.1021/ja00305a055
Corey, 1981, Total synthesis of the quinonoid alcohol dehydrogenase coenzyme of methylotrophic bacteria, J. Am. Chem. Soc., 103, 5599, 10.1021/ja00408a067
de Beer, 1980, The prosthetic group of methylamine dehydrogenase from Pseudomonas AM1, Biochim. Biophys. Acta, 622, 370, 10.1016/0005-2795(80)90050-1
Dekker, 1982, Covalent addition of H2O, enzyme substrates and activators to pyrroloquinoline quinone, the coenzyme of quinoproteins, Eur. J. Biochem., 125, 69, 10.1111/j.1432-1033.1982.tb06652.x
Duine, 1988, Unity and diversity in biological redox catalysis: Comparative enzymology of some microbial oxidoreductases showing variation in cofactor identity, 671
Duine, 1980, The prosthetic group of methanol dehydrogenase. Purification and some properties, Biochem. J., 187, 213, 10.1042/bj1870213
Duine, 1981, Quinoproteins: A novel class of dehydrogenases, Trends Biochem. Sci., 6, 278, 10.1016/0968-0004(81)90100-6
Duine, 1989, Quinoprotein enzymes, Annu. Rev. Biochem., 58, 403, 10.1146/annurev.bi.58.070189.002155
Duine, 1978, Purification and properties of methanol dehydrogenase from Hyphomicrobium X, Biochim. Biophys. Acta, 524, 277, 10.1016/0005-2744(78)90164-X
Duine, 1979, Glucose dehydrogenase from Acinetobacter calcoaceticus: A quinoprotein, FEBS Lett., 108, 443, 10.1016/0014-5793(79)80584-0
Duine, 1980, Structure and activity of the prosthetic group of methanol dehydrogenase, Eur. J. Biochem., 108, 187, 10.1111/j.1432-1033.1980.tb04711.x
Duine, 1981, Characterization of the second prosthetic group in methanol dehydrogenase from Hyphomicrobium X, Eur. J. Biochem., 118, 395, 10.1111/j.1432-1033.1981.tb06415.x
Duine, 1983, Detection and determination of pyrroloquinoline quinone, the coenzyme of quinoproteins, Anal. Biochem., 133, 239, 10.1016/0003-2697(83)90249-X
Duine, 1985, 79
Duine, 1986, PQQ and quinoprotein enzymes in microbial oxidations, FEMS Microbiol. Rev., 32, 165, 10.1111/j.1574-6968.1986.tb01191.x
Duine, 1987, Enzymology of quinoproteins, Adv. Enzymol., 59, 169
Duine, 1987, Copper-containing amine oxidases (EC 1.4.3.6) have covalently-bound PQQ and not PLP as organic cofactor, 243
Eipper, 1983, Identification in pituitary tissue of a peptide α-amidation activity that acts on glycine-extended peptides and requires molecular oxygen, copper, and ascorbic acid, Proc. Natl. Acad. Sci. U.S.A., 80, 5144, 10.1073/pnas.80.16.5144
Eirich, 1978, Proposed structure for coenzyme F420 from Methanobacterium, Biochemistry, 17, 4583, 10.1021/bi00615a002
Eker, 1980, Photoreactivating enzyme from Streptomyces griseus, Photochem. Photobiol., 33, 65, 10.1111/j.1751-1097.1981.tb04298.x
Faraggi, 1986, The methoxatin semiquinone. A pulse radiolysis study, Biochem. Biophys. Res. Commun., 139, 955, 10.1016/S0006-291X(86)80270-4
Flueckiger, 1988, The interaction of aminogroups with pyrroloquinoline quinone as detected by the reduction of nitroblue tetrazolium, Biochem. Biophys. Res. Commun., 153, 353, 10.1016/S0006-291X(88)81230-0
Gainor, 1982, Synthesis of the bacterial coenzyme methoxatin, J. Org. Chem., 47, 2833, 10.1021/jo00136a002
Geiger, 1987, Enzymatic determination of pyrroloquinoline quinone using crude membranes from Escherichia coli, Anal. Biochem., 164, 418, 10.1016/0003-2697(87)90513-6
Glatz, 1987, Pea (Pisum sativum) diamine oxidase contains pyrroloquinoline quinone as a cofactor, Biochem. J., 242, 603, 10.1042/bj2420603
Goosen, 1987, Cloning of the genes involved in synthesis of coenzyme pyrroloquinoline quinone from Acinetobacter calcoaceticus, J. Bacteriol., 169, 303, 10.1128/jb.169.1.303-307.1987
Groen, 1986, Quinohaemoprotein alcohol dehydrogenase apoenzyme from Pseudomonas testosteroni, Biochem. J., 234, 611, 10.1042/bj2340611
Hanauske-Abel, 1987, Pyrroloquinoline quinone and molecules mimicking its functional domains. Modulators of connective tissue formation?, FEBS Lett., 214, 236, 10.1016/0014-5793(87)80062-5
Hauge, 1964, Glucose dehydrogenase of Bacterium anitratum: An enzyme with a novel prosthetic group, J. Biol. Chem., 239, 3630, 10.1016/S0021-9258(18)91183-X
Hendrickson, 1984, Total synthesis of the novel coenzyme methoxatin, J. Org. Chem., 50, 1688, 10.1021/jo00210a024
Hommes, 1984, Evidence of a quinoprotein glucose dehydrogenase apoenzyme in several strains of Escherichia coli, FEMS Microbiol. Lett., 24, 329, 10.1111/j.1574-6968.1984.tb01329.x
Houck, 1988, PQQ: Biosynthetic studies in Methylobacterium AM1 using specific 13C-labeling and NMR, J. Am. Chem. Soc., 110, 6920, 10.1021/ja00228a070
Imanaga, 1979, Glucose dehydrogenase from Pseudomonas fluorescens, Proc. Jpn. Acad., 558, 264, 10.2183/pjab.55.264
1984
Itoh, 1987, Synthesis of pyrroloquinoline quinone derivatives: Model compounds of a novel coenzyme PQQ (methoxatin), Synthesis, 12, 163
Jongejan, 1987, Spectrophotometric studies on pyrroloquinoline quinone-Cu(II) complexes as possible models for copper-quinoprotein amine oxidases, Recl. Trav. Chim. Pays-Bas, 106, 365
Jongejan, 1988, Synthesis of 13C- and 2H-labelled PQQ, Tetrahedron Lett., 29, 3709, 10.1016/S0040-4039(00)82160-7
Kilty, 1982, Reconstitution of glucose dehydrogenase using synthetic methoxatin, Arch. Biochem. Biophys., 218, 623, 10.1016/0003-9861(82)90389-7
Knowles, 1987, The organic cofactor in plasma amine oxidase: Evidence for pyrroloquinoline quinone and against pyridoxal phosphate, Biochem. J., 241, 603, 10.1042/bj2410603
Kramer, 1987, The structure of the molybdenum cofactor. Characterization of di-(carboxamidomethyl)molybdopterin from sulfite oxidase and xanthine oxidase, J. Biol. Chem., 262, 16357, 10.1016/S0021-9258(18)49263-0
Leigh, 1984, Proposed structure for coenzyme F420 from Methanobacterium, J. Am. Chem. Soc., 106, 3636, 10.1021/ja00324a037
Lobenstein-Verbeek, 1984, Bovine serum amine oxidase: A mammalian enzyme having covalently-bound PQQ as prosthetic group, FEBS Lett., 170, 305, 10.1016/0014-5793(84)81333-2
MacKenzie, 1986, Synthesis of the bacterial coenzyme methoxatin, Tetrahedron, 42, 3259, 10.1016/S0040-4020(01)87390-7
Matsumoto, 1989, 162
McCormick, 1982, Identity of cosynthetic factor 1 of Streptomyces aureofaciens and fragment FO of Methanobacterium species, J. Am. Chem. Soc., 104, 4014, 10.1021/ja00378a044
Meyer, 1986, Biochemistry and physiology of aerobic carbon monoxide-utilizing bacteria, FEMS Microbiol. Rev., 39, 161, 10.1111/j.1574-6968.1986.tb01858.x
Moog, 1986, Evidence for methoxatin (pyrroloquinoline quinone) as the cofactor in bovine plasma amine oxidase from resonance Raman spectroscopy, Proc. Natl. Acad. Sci. U.S.A., 83, 8435, 10.1073/pnas.83.22.8435
Nagasawa, 1987, Nitrile hydratase is a quinoprotein. A possible new function of pyrroloquinoline quinone: Activation of H2O in an enzymatic hydration reaction, Biochem. Biophys. Res. Commun., 147, 701, 10.1016/0006-291X(87)90987-9
Niederpruem, 1965, Cofactor-dependent aldose dehydrogenase of Rhodopseudomonas spheroides, J. Bacteriol., 89, 697, 10.1128/JB.89.3.697-705.1965
Noar, 1987, Decarboxylated methoxatin analogues. Synthesis of 7- and 9-decarboxymethoxatin, J. Org. Chem., 52, 1942, 10.1021/jo00386a010
Noar, 1985, Synthesis of 9-decarboxymethoxatin. Metal complexation of methoxatin as a possible requirement for its biological activity, J. Am. Chem. Soc., 107, 7198, 10.1021/ja00310a086
Noll, 1986, Structure of component B (7-mercaptoheptanoylthreonine phosphate) of the methylcoenzyme M methylreductase system of Methanobacterium autotrophicum, Proc. Natl. Acad. Sci. U.S.A., 83, 4238, 10.1073/pnas.83.12.4238
Pfaltz, 1982, Zur Kenntniss des Faktors F430 aus methanogenen Bacterien: Struktur des porphinoiden Ligand Systems, Helv. Chim. Acta, 65, 828, 10.1002/hlca.19820650320
Prince, 1988, Tyrosyl radicals, Trends Biochem. Sci., 13, 286, 10.1016/0968-0004(88)90119-3
Recsei, 1984, Pyruvoyl enzymes, Annu. Rev. Biochem., 53, 357, 10.1146/annurev.bi.53.070184.002041
Riceberg, 1975, Effects of aminoacetonitrile, an amine oxidase inhibitor, on mescaline metabolism in the rabbit, Biochem. Pharmacol., 24, 119, 10.1016/0006-2952(75)90323-8
Salisbury, 1979, A novel coenzyme from bacterial primary alcohol dehydrogenases, Nature (London), 280, 843, 10.1038/280843a0
Shinagawa, 1986, The 9-carboxyl group of pyrroloquinoline quinone, a novel prosthetic group, is essential in the formation of holoenzyme of d-glucose dehydrogenase, Biochem. Biophys. Res. Commun., 139, 1279, 10.1016/S0006-291X(86)80316-3
Sleath, 1985, J. Am. Chem. Soc., 107, 3328, 10.1021/ja00297a044
Sperl, 1974, Substrate specificity of the purified primary alcohol dehydrogenase from methanol oxidizing bacteria, J. Bacteriol., 118, 541, 10.1128/JB.118.2.541-550.1974
Suzuki, 1989, 123
Taylor, 1974, Structure and methylation of coenzyme M (HSCH2CH2SO3), J. Biol. Chem., 249, 4879, 10.1016/S0021-9258(19)42403-4
Theorell, 1935, Reindarstellung der Wirkungsgruppe der gelben Ferment, Biochem. Z., 275, 344
Urushibara, 1971, Pteridines produced by Methylococcus capsulatus. Isolation and identification of neopterin 2′,3′-phosphate, Biochem. J., 125, 141, 10.1042/bj1250141
van Beelen, 1984, Elucidation of the structure of methanopterin, a coenzyme from Methanobacterium autotrophicum, using two-dimensional nuclear-magnetic-resonance techniques, Eur. J. Biochem., 138, 563, 10.1111/j.1432-1033.1984.tb07951.x
van der Meer, 1986, Covalently-bound pyrroloquinoline quinone is the organic prosthetic group in human placental lysyloxidase, Biochem. J., 239, 789, 10.1042/bj2390789
van der Meer, 1988, Pyrroloquinoline quinone (PQQ) is the organic cofactor in soybean lipoxygenase-1, FEBS Lett., 235, 194, 10.1016/0014-5793(88)81261-4
van der Meer, 1986, Hydrazone formation of 2,4-dinitrophenylhydrazine with PQQ in porcine kidney diamine oxidase, FEBS Lett., 206, 211, 10.1016/0014-5793(86)81350-3
van der Meer, 1987, Phenylhydrazine as probe for cofactor identification in amine oxidoreductases. Evidence for PQQ as the cofactor in methylamine dehydrogenase, FEBS Lett., 221, 299, 10.1016/0014-5793(87)80944-4
van der Meer, 1988, Dopamine β-hydroxylase from bovine medulla contains covalently-bound pyrroloquinoline quinone, FEBS Lett., 231, 303, 10.1016/0014-5793(88)80838-X
van der Meer, 1989, On the biosynthesis of free and covalently bound PQQ. Glutamic acid decarboxylase from Escherichia coli is a pyridoxo-quinoprotein, FEBS Lett., 246, 109, 10.1016/0014-5793(89)80263-7
van der Meer, 1989, Primary structure of a pyrroloquinoline quinone (PQQ) containing peptide isolated from procine kidney diamine oxidase, Biochem. Biophys. Res. Commun., 159, 726, 10.1016/0006-291X(89)90055-7
van Iersel, 1986, Methylamine oxidase from Arthrobacter P1: A bacterial copper-quinoprotein amine oxidase, Eur. J. Biochem., 161, 415, 10.1111/j.1432-1033.1986.tb10461.x
van Kleef, 1988, Bacterial NAD(P)-independent quinate dehydrogenase is a quinoprotein, Arch. Microbiol., 150, 32, 10.1007/BF00409714
van Kleef, 1988, l-tyrosine is the precursor of PQQ biosynthesis in Hyphomicrobium X, FEBS Lett., 237, 91, 10.1016/0014-5793(88)80178-9
van Kleef, 1988, A search for intermediates in the bacterial biosynthesis of PQQ, BioFactors, 1, 297
van Kleef, 1989, Factors relevant in bacterial pyrroloquinoline quinone production, Appl. Environ. Microbiol., 55, 10.1128/AEM.55.5.1209-1213.1989
van Kleef, 1987, Detection of PQQ, Anal. Biochem., 162, 143, 10.1016/0003-2697(87)90019-4
van Koningsveld, 1985, Structure of the 2,4-dinitrophenylhydrazine adduct of pyrroloquinoline quinone (PQQ) dimethyl ethyl triester, C24H18N6011, Acta Crystallogr., Sect. C, C41, 92
van Schie, 1984, Non-coordinated synthesis of glucose dehydrogenase and its prosthetic group PQQ in Acinetobacter and Pseudomonas species, FEMS Microbiol. Lett., 24, 133
van Schie, 1987, PQQ-dependent production of gluconic acid by Acinetobacter, Agrobacterium and Rhizobium species, J. Gen. Microbiol., 133, 867
Vellieux, 1986, Purification, crystallization and preliminary X-ray investigation of quinoprotein methylamine dehydrogenase from Thiobacillus versutus, Eur. J. Biochem., 154, 383, 10.1111/j.1432-1033.1986.tb09409.x
Westerling, 1979, The prosthetic group of methanol dehydrogenase from Hyphomicrobium X: Electron spin evidence for a quinone structure, Biochem. Biophys. Res. Commun., 87, 719, 10.1016/0006-291X(79)92018-7
Williamson, 1986, Evidence for pyrroloquinoline quinone as the carbonyl cofactor in lysyl oxidase by absorption and resonance Raman spectroscopy, J. Biol. Chem., 261, 16302, 10.1016/S0021-9258(18)66565-2
Winters-Ivey, 1989, 35
Wood, 1953, Carbohydrate oxidation by Pseudomonas fluorescens. I. The mechanism of glucose and gluconate oxidation, J. Biol. Chem., 201, 501, 10.1016/S0021-9258(18)66204-0
Xiong, 1988, Stimulation of Lillium pollen germination by pyrroloquinoline quinone, Agric. Biol. Chem., 52, 1065, 10.1271/bbb1961.52.1065
