Issue 31, 2005
From the journal:

Chemical Communications

cis-Dihydrodiol, arene oxide and phenolmetabolites of dictamnine: key intermediates in the biodegradation and biosynthesis of furoquinolinealkaloids

Derek R. Boyd,*ab   Narain D. Sharma,ab   Colin R. O'Dowd,a   Jonathan G. Carroll,a   Pui L. Lokea  and  Christopher C. R. Allenc  

* Corresponding authors

a School of Chemistry, The Queen's University of Belfast, Belfast, UK
E-mail: dr.boyd@qub.ac.uk
Fax: +44 (0)2890 382117
Tel: +44 (0)2890 681198

b CenTACat, The Queen's University of Belfast, Belfast, UK

c QUESTOR, The Queen's University of Belfast, Belfast, UK

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.

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

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Article information

DOI
https://doi.org/10.1039/B506944K
Article type
Communication
Submitted
18 May 2005
Accepted
06 Jun 2005
First published
11 Jul 2005

Chem. Commun., 2005, 3989-3991

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

D. R. Boyd, N. D. Sharma, C. R. O'Dowd, J. G. Carroll, P. L. Loke and C. C. R. Allen, Chem. Commun., 2005, 3989 DOI: 10.1039/B506944K

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