UNSPECIFIED. (2002) Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 80 (6). pp. 589-600. ISSN 0008-4042

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Abstract

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.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Journal or Publication Title:	CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
Publisher:	NATL RESEARCH COUNCIL CANADA
ISSN:	0008-4042
Date:	June 2002
Volume:	80
Number:	6
Number of Pages:	12
Page Range:	pp. 589-600
Identification Number:	10.1139/v02-062
Publication Status:	Published
URI:	http://wrap.warwick.ac.uk/id/eprint/10760

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