title: Intermediate analogue inhibitors of mandelate racemase: N-Hydroxyformanilide and cupferron.
abstract: Mandelate racemase (MR) catalyzes the 1,1-proton transfer that interconverts the enantiomers of mandelate. The transition state/intermediate analogues N-hydroxyformanilide (K(i)=2.79+/-0.19 microM) and cupferron (K(i)=2.67+/-0.09 microM) are identified as potent competitive inhibitors of MR. The pH-pK(i) profile indicates that MR can bind either the protonated or deprotonated forms of N-hydroxyformanilide, with a 10-fold greater affinity for the latter form.
authors.affiliation: Department of Biochemistry and Molecular Biology, Dalhousie University, Halifax, Nova Scotia, Canada.
authors.forename: Jennifer R
authors.initials: JR
authors.lastname: Bourque
authors.forename: Rodney K M
authors.initials: RK
authors.lastname: Burley
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Bearne
mesh_terms: D004791:Enzyme Inhibitors / Q000737:chemistry*; D005559:Formamides / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009602:Nitrosamines / Q000737:chemistry*; D016958:Pseudomonas putida / Q000201:enzymology*; D019998:Racemases and Epimerases / Q000037:antagonists & inhibitors* / Q000737:chemistry; D013379:Substrate Specificity
chemical_list: D004791:Enzyme Inhibitors; D005559:Formamides; D009602:Nitrosamines; D019998:Racemases and Epimerases; C021540:mandelate racemase; C031808:cupferron