Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems
Data(s) |
2002
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Resumo |
Toluene dioxygenase-catalyzed dihydroxylation, in the carbocyclic rings of quinoline, 2-chloroquinoline, 2-methoxyquinoline, and 3-bromoquinoline, was found to yield the corresponding enantiopure cis-5,6- and -7,8-dihydrodiol metabolites using whole cells of Pseudomonas putida UV4. cis-Dihydroxylation at the 3,4-bond of 2-chloroquinoline, 2-methoxyquinoline, and 2-quinolone was also found to yield the heterocyclic cis-dihydrodiol metabolite, (+)-cis-(3S,4S)-3,4-dihydroxy-3,4-dihydro-2-quinolone. Heterocyclic cis-dihydrodiol metabolites, resulting from dihydroxylation at the 5,6- and 3,4-bonds of 1-methyl 2-pyridone, were isolated from bacteria containing toluene, naphthalene, and biphenyl dioxygenases. The enantiomeric excess (ee) values (>98%) and the absolute configurations of the carbocyclic cis-dihydrodiol metabolites of quinoline substrates (benzylic R) and of the heterocyclic cis-diols from quinoline, 2-quinolone, and 2-pyridone substrates (allylic S) were found to be in accord with earlier models for dioxygenase-catalyzed cis-dihydroxylation of carbocyclic arenes. Evidence favouring the dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems is presented. |
Identificador |
http://dx.doi.org/10.1139/V02-062 http://www.scopus.com/inward/record.url?scp=18544363057&partnerID=8YFLogxK |
Idioma(s) |
eng |
Direitos |
info:eu-repo/semantics/restrictedAccess |
Fonte |
Boyd , D , Sharma , N , Modyanova , L V , Carroll , J G , Malone , J , Allen , C , Hamilton , J , Gibson , D , Parales , R E & Dalton , H 2002 , ' Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems ' CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE , vol 80 , no. 6 , pp. 589-600 . DOI: 10.1139/V02-062 |
Palavras-Chave | #/dk/atira/pure/subjectarea/asjc/1600 #Chemistry(all) |
Tipo |
article |