Issue 11, 2009
From the journal:

Organic & Biomolecular Chemistry

Synthesis and evaluation of 2,5-dihydrochorismate analogues as inhibitors of the chorismate-utilising enzymes†

Richard J. Payne,*ab   Esther M. M. Bulloch,a   Miguel M. Toscano,a   Michelle A. Jones,a   Olivier Kerbarha  and  Chris Abell*a  

* Corresponding authors

a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK
E-mail: ca26@cam.ac.uk
Fax: +44 1223 336362
Tel: +44 1223 336405

b School of Chemistry, University of Sydney, Building F11, Sydney, Australia
E-mail: payne@chem.usyd.edu.au

Abstract

A library of 2,5-dihydrochorismate analogues were designed as inhibitors of the chorismate-utilising enzymes including anthranilate synthase, isochorismate synthase, salicylate synthase and 4-amino-4-deoxychorismate synthase. The inhibitors were synthesised in seven or eight steps from shikimic acid, sourced from star anise. The compounds exhibited moderate but differential inhibition against the four chorismate-utilising enzymes.

Graphical abstract: Synthesis and evaluation of 2,5-dihydrochorismate analogues as inhibitors of the chorismate-utilising enzymes

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Article information

DOI
https://doi.org/10.1039/B901694E
Article type
Paper
Submitted
27 Jan 2009
Accepted
06 Mar 2009
First published
02 Apr 2009

Org. Biomol. Chem., 2009,7, 2421-2429

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Synthesis and evaluation of 2,5-dihydrochorismate analogues as inhibitors of the chorismate-utilising enzymes

R. J. Payne, E. M. M. Bulloch, M. M. Toscano, M. A. Jones, O. Kerbarh and C. Abell, Org. Biomol. Chem., 2009, 7, 2421 DOI: 10.1039/B901694E

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