Issue 11, 2004
From the journal:

Organic & Biomolecular Chemistry

(1R,4S,5R)-3-Fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid: the fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases

Martyn Frederickson,a   Aleksander W. Roszak,b   John R. Coggins,c   Adrian J. Lapthornb  and  Chris Abell*a  

* Corresponding authors

a University Chemical Laboratory, Lensfield Road, Cambridge, UK
E-mail: ca26@cam.ac.uk
Fax: +44 (0)1223 336362
Tel: +44 (0)1223 336405

b Department of Chemistry, University of Glasgow, Glasgow, UK

c Division of Biochemistry and Molecular Biology, Institute of Biomedical and Life Sciences, University of Glasgow, Glasgow, UK

Abstract

The fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases has been prepared from naturally occuring (−)-quinic acid over seven steps and has been shown to be the most potent inhibitor reported to date of the type II enzyme from Mycobacterium tuberculosis.

Graphical abstract: (1R,4S,5R)-3-Fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid: the fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases

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Article information

DOI
https://doi.org/10.1039/B404535A
Article type
Paper
Submitted
29 Mar 2004
Accepted
19 Apr 2004
First published
06 May 2004

Org. Biomol. Chem., 2004,2, 1592-1596

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(1R,4S,5R)-3-Fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid: the fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases

M. Frederickson, A. W. Roszak, J. R. Coggins, A. J. Lapthorn and C. Abell, Org. Biomol. Chem., 2004, 2, 1592 DOI: 10.1039/B404535A

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