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Titolo:
SYNTHESIS OF ISOMERIC ANALOGS OF COENZYME PYRROLOQUINOLINE QUINONE (PQQ)
Autore:
ZHANG ZP; TILLEKERATNE LMV; HUDSON RA;
Indirizzi:
UNIV TOLEDO,COLL PHARM,DEPT MED & BIOL CHEM,2801 W BANCROFT ST TOLEDOOH 43606 UNIV TOLEDO,COLL PHARM,DEPT MED & BIOL CHEM TOLEDO OH 43606 UNIV TOLEDO,COLL ARTS & SCI,DEPT CHEM TOLEDO OH 43606
Titolo Testata:
Synthesis
fascicolo: 3, , anno: 1996,
pagine: 377 -
SICI:
0039-7881(1996):3<377:SOIAOC>2.0.ZU;2-H
Fonte:
ISI
Lingua:
ENG
Soggetto:
DEHYDROGENASE; REDUCTASE; INJURY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
35
Recensione:
Indirizzi per estratti:
Citazione:
Z.P. Zhang et al., "SYNTHESIS OF ISOMERIC ANALOGS OF COENZYME PYRROLOQUINOLINE QUINONE (PQQ)", Synthesis, (3), 1996, pp. 377

Abstract

Three isomeric analogues 2-4 of the redox-active coenzyme oxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid (1, PQQ, methoxatin) weresynthesized from methoxynitroanilines 8, 9 and 10 a, respectively. Reaction of the diazonium salts of each of the starting compounds with ethyl alpha-methylacetoacetate gave the corresponding substituted phenylhydrazones of ethyl pyruvate. These intermediates underwent acid-catalyzed Fischer indolization and gave the esters 13, 17 and 25, respectively. Reduction to the corresponding aminoindoles with hydrogen over Pd/C, followed by Doebner-von Miller quinoline synthesis with dimethyl trans-2-ketoglutaconate, oxidation of the intermediate methoxy compound to the o-quinone, and hydrolysis of triester products gave 2, 3, and4, respectively. These isomers will serve as authentic examples to define their possible formation in nature and will also serve as isosteric probes to define the binding of PQQ at active sites in PQQ-requiring quinoproteins.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 13/07/20 alle ore 11:12:18