Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems

Derek Boyd, Narain Sharma, L.V. Modyanova, J.G. Carroll, John Malone, Christopher Allen, John Hamilton, David Gibson, R.E. Parales, H. Dalton

Research output: Contribution to journalArticle

36 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)589-600
Number of pages12
JournalCANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
Volume80
Issue number6
DOIs
Publication statusPublished - 2002

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems'. Together they form a unique fingerprint.

  • Cite this

    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, 80(6), 589-600. https://doi.org/10.1139/V02-062