cis-Dihydrodiol, arene oxide and phenol metabolites of dictamnine: key intermediates in the biodegradation and biosynthesis of furoquinoline alkaloids.
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.
Boyd
Derek R
DR
School of Chemistry, Queen's University of Belfast, Belfast, UK BT9 5AG. dr.boyd@qub.ac.uk
Sharma
Narain D
ND
O'Dowd
Colin R
CR
Carroll
Jonathan G
JG
Loke
Pui L
PL
Allen
Christopher C R
CC
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
D000470:Alkaloids; D009281:Naphthalenes; D010087:Oxides; D010636:Phenols; D011804:Quinolines; C507866:trans-1,2-dihydro-1,2-naphthalenediol; C026398:dictamnine