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

Richard J. Payne; Esther M. M. Bulloch; Miguel M. Toscano; Michelle A. Jones; Olivier Kerbarh; Chris Abell

doi:10.1039/B901694E

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Organic & Biomolecular Chemistry

Issue 11, 2009

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

Richard J. Payne , Esther M. M. Bulloch , Miguel M. Toscano , Michelle A. Jones , Olivier Kerbarh and Chris Abell

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

DOI: 10.1039/B901694E
Received 27 Jan 2009, Accepted 06 Mar 2009
First published on the web 02 Apr 2009

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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.

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Richard J. Payne
Esther M. M. Bulloch
Miguel M. Toscano
Michelle A. Jones
Olivier Kerbarh
Chris Abell

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Organic & Biomolecular Chemistry

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

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