cis-Dihydrodiol, arene oxide and phenol metabolites of dictamnine: key intermediates in the biodegradation and biosynthesis of furoquinoline alkaloids

DR Boyd, ND Sharma, CR O'Dowd, JG Carroll…

Index: Boyd, Derek R.; Sharma, Narain D.; O'Dowd, Colin R.; Carroll, Jonathan G.; Loke, Pui L.; Allen, Christopher C. R. Chemical Communications, 2005 , # 31 p. 3989 - 3991

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Citation Number: 14

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 ...