Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates

Derek Boyd, Narain Sharma, Gerard P. Coen, Francis Hempenstall, Vera Ljubez, John Malone, Christopher Allen, John Hamilton

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

cis-Dihydrodiol metabolites were obtained from dioxygenase-catalysed asymmetric dihydroxylations of. five monocyclic (azabiphenyl) and four tricyclic (azaphenanthrene) azaarene substrates. Enantiopurity values and absolute configuration assignments were determined using a combination of stereochemical correlation, X-ray crystallography and spectroscopy methods. The degree of regioselectivity found during cis-dihydroxylation of monocyclic azaarenes (2,3 bond >> 3,4 bond) and of tricyclic azaarenes (bay region > non-bay region bonds) was dependent on the type of dioxygenase used. The cis-dihydrodiol metabolite from an azaarene (3-phenylpyridine) was utilised in the chemoenzymatic synthesis of the corresponding trans-dihydrodiol.
Original languageEnglish
Pages (from-to)3957-3966
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume6
Issue number21
DOIs
Publication statusPublished - 2008

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Medicine(all)

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