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Bioorg Med Chem. 2008 Dec 1;16(23):9975-83. doi: 10.1016/j.bmc.2008.10.026. Epub 2008 Oct 17.

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

Author information

1
School of Chemistry, University of Melbourne, Parkville, Vic. 3010, Australia.

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.

PMID:
18977662
DOI:
10.1016/j.bmc.2008.10.026
[Indexed for MEDLINE]

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