Biphenyl dioxygenase-catalysed cis-dihydroxylation of tricyclic azaarenes: chemoenzymatic synthesis of arene oxide metabolites and furoquinoline alkaloids

Derek R. Boyd*, Narain D. Sharma, Jonathan G. Carroll, Pui L. Loke, Colin R. O'Dowd, Christopher C. R. Allen

*Corresponding author for this work

Research output: Contribution to journalArticle

9 Citations (Scopus)
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Abstract

Biotransformation of acridine, dictamnine and 4-chlorofuro[2,3-b]quinolone, using whole cells of Sphingomonas yanoikuyae B8/36, yielded five enantiopure cyclic cis-dihydrodiols, from biphenyl dioxygenase-catalysed dihydroxylation of the carbocyclic rings. cis-Dihydroxylation of the furan ring in dictamnine and 4-chlorofuro[2,3-b] quinoline, followed by ring opening and reduction, yielded two exocyclic diols. The structures and absolute configurations of metabolites have been determined by spectroscopy and stereochemical correlation methods. Enantiopure arene oxide metabolites of acridine and dictamnine have been synthesised, from the corresponding cis-dihydrodiols. The achiral furoquinoline alkaloids robustine, gamma-fagarine, haplopine, isohaplopine-3,3'-dimethylallylether and pteleine have been obtained, from either cis-dihydrodiol, catechol or arene oxide metabolites of dictamnine.

Original languageEnglish
Pages (from-to)10944-10955
Number of pages12
JournalRSC Advances
Volume3
Issue number27
Early online date03 May 2013
DOIs
Publication statusPublished - 2013

Keywords

  • QUINOLINE ALKALOIDS
  • SALMONELLA-TYPHIMURIUM
  • NITROGEN HETEROCYCLE
  • LITHIATION REACTIONS
  • PSEUDOMONAS-PUTIDA
  • PHENOL METABOLITES
  • TRANS-DIHYDRODIOL
  • GAMMA-FAGARINE
  • DIOL EPOXIDE
  • AZA-ARENES

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

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