title: cis-Dihydrodiol, arene oxide and phenol metabolites of dictamnine: key intermediates in the biodegradation and biosynthesis of furoquinoline alkaloids.
abstract: Biotransformation of the parent furoquinoline alkaloid dictamnine and its 4-chlorofuroquinoline precursor, using the B8/36 bacterial mutant strain of Sphingomonas yanoikuyae, yielded, via biphenyl dioxygenase-catalysed dihydroxylation, the first isolable alkaloid cis-dihydrodiol metabolites; these metabolites were used in the chemoenzymatic synthesis of postulated arene oxide and phenol intermediates, and a range of derived furoquinoline alkaloids.
authors.affiliation: School of Chemistry, Queen's University of Belfast, Belfast, UK BT9 5AG. dr.boyd@qub.ac.uk
authors.forename: Derek R
authors.initials: DR
authors.lastname: Boyd
authors.forename: Narain D
authors.initials: ND
authors.lastname: Sharma
authors.forename: Colin R
authors.initials: CR
authors.lastname: O'Dowd
authors.forename: Jonathan G
authors.initials: JG
authors.lastname: Carroll
authors.forename: Pui L
authors.initials: PL
authors.lastname: Loke
authors.forename: Christopher C R
authors.initials: CC
authors.lastname: Allen
mesh_terms: D000470:Alkaloids / Q000096:biosynthesis / Q000737:chemistry / Q000378:metabolism*; D009281:Naphthalenes / Q000378:metabolism*; D010087:Oxides / Q000378:metabolism*; D010636:Phenols / Q000378:metabolism*; D011804:Quinolines / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000470:Alkaloids; D009281:Naphthalenes; D010087:Oxides; D010636:Phenols; D011804:Quinolines; C507866:trans-1,2-dihydro-1,2-naphthalenediol; C026398:dictamnine