title: Synthesis and evaluation of 2,5-dihydrochorismate analogues as inhibitors of the chorismate-utilising enzymes.
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.
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UKCB2 1EW. payne@chem.usyd.edu.au
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Payne
authors.forename: Esther M M
authors.initials: EM
authors.lastname: Bulloch
authors.forename: Miguel M
authors.initials: MM
authors.lastname: Toscano
authors.forename: Michelle A
authors.initials: MA
authors.lastname: Jones
authors.forename: Olivier
authors.initials: O
authors.lastname: Kerbarh
authors.forename: Chris
authors.initials: C
authors.lastname: Abell
mesh_terms: D000878:Anthranilate Synthase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D001426:Bacterial Proteins / Q000378:metabolism*; D019731:Carbon-Nitrogen Ligases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D002827:Chorismic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000378:metabolism; D004926:Escherichia coli / Q000201:enzymology; D019751:Intramolecular Transferases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D008190:Lyases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D012706:Serratia marcescens / Q000201:enzymology; D000637:Transaminases
chemical_list: D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D000637:Transaminases; C066599:aminodeoxychorismate synthase; D008190:Lyases; C022620:salicylate synthetase; D000878:Anthranilate Synthase; D019751:Intramolecular Transferases; C058486:isochorismate synthase; D019731:Carbon-Nitrogen Ligases; D002827:Chorismic Acid