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Irreversible inhibition of dihydrodipicolinate synthase by 4-oxo-heptenedioic acid analogues

Boughton, B.A.ORCID: 0000-0001-6342-9814, Griffin, M.D.W., O’Donnell, P.A., Dobson, R.C.J., Perugini, M.A., Gerrard, J.A. and Hutton, C.A. (2008) Irreversible inhibition of dihydrodipicolinate synthase by 4-oxo-heptenedioic acid analogues. Bioorganic & Medicinal Chemistry, 16 (23). pp. 9975-9983.

Link to Published Version: https://doi.org/10.1016/j.bmc.2008.10.026
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Abstract

We report the synthesis of (2E,5E)-4-oxoheptadienedioic acid and (2E)-4-oxoheptenedioic acid and evaluation of both diester and diacid analogues as inhibitors of bacterial dihydrodipicolinate synthase. Enzyme kinetic studies allowed the determination of second-order rate constants of inactivation; and substrate co-incubation studies have shown the inhibitors act at the active-site. Mass spectrometric analyses have further explored the enzyme–inhibitor interaction and determined the sites of enzyme alkylation.

Item Type: Journal Article
Publisher: Elsevier
Copyright: © 2008 Elsevier Ltd
URI: http://researchrepository.murdoch.edu.au/id/eprint/56484
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