Intermediate analogue inhibitors of mandelate racemase: N-Hydroxyformanilide and cupferron

descriptionPublicationkeyboard_double_arrow_right Article 01 Jan 2007 English Publisher:Elsevier BVJournal:Bioorganic & Medicinal Chemistry Letters, volume 17, pages 105-108 (issn: 0960-894X,

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Authors: Jennifer R, Bourque; Rodney K M, Burley; Stephen L, Bearne;

doi: 10.1016/j.bmcl.2006.09.079

pmid: 17055725

Intermediate analogue inhibitors of mandelate racemase: N-Hydroxyformanilide and cupferron

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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.

Related Organizations

Dalhousie University
Canada

Keywords

Nitrosamines, Formamides, Pseudomonas putida, Racemases and Epimerases, Enzyme Inhibitors, Hydrogen-Ion Concentration, Substrate Specificity

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