Issue 21, 2008
From the journal:

Organic & Biomolecular Chemistry

Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates†

Derek R. Boyd,*a   Narain D. Sharma,a   Gerard P. Coen,a   Francis Hempenstall,a   Vera Ljubez,a   John F. Malone,a   Christopher C. R. Allenb  and  John T. G. Hamiltonbc  

* Corresponding authors

a School of Chemistry and Chemical Engineering, The Queen's University of Belfast, Belfast, UK
E-mail: dr.boyd@qub.ac.uk
Tel: +44 (0)28-90974421

b School of Biological Sciences, The Queen's University of Belfast, Belfast, UK

c Agri-food and Biosciences Institute for Northern Ireland, Newforge Lane, Belfast, UK

Abstract

cis-Dihydrodiol metabolites were obtained from dioxygenase-catalysed asymmetric dihydroxylations of five monocyclic (azabiphenyl) and four tricyclic (azaphenanthrene) azaarene substrates. Enantiopurity values and absolute configuration assignments were determined using a combination of stereochemical correlation, X-ray crystallography and spectroscopy methods. The degree of regioselectivity found during cis-dihydroxylation of monocyclic azaarenes (2,3 bond >> 3,4 bond) and of tricyclic azaarenes (bay region > non-bay region bonds) was dependent on the type of dioxygenase used. The cis-dihydrodiol metabolite from an azaarene (3-phenylpyridine) was utilised in the chemoenzymatic synthesis of the corresponding trans-dihydrodiol.

Graphical abstract: Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates

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Article information

DOI
https://doi.org/10.1039/B810235J
Article type
Paper
Submitted
17 Jun 2008
Accepted
29 Jul 2008
First published
05 Sep 2008

Org. Biomol. Chem., 2008,6, 3957-3966

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Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates

D. R. Boyd, N. D. Sharma, G. P. Coen, F. Hempenstall, V. Ljubez, J. F. Malone, C. C. R. Allen and J. T. G. Hamilton, Org. Biomol. Chem., 2008, 6, 3957 DOI: 10.1039/B810235J

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