Bioorganic & Medicinal Chemistry 2008-12-01

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

Berin A Boughton, Michael D W Griffin, Paul A O'Donnell, Renwick C J Dobson, Matthew A Perugini, Juliet A Gerrard, Craig A Hutton

Index: Bioorg. Med. Chem. 16 , 9975-83, (2008)

Full Text: HTML

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.

Related Compounds

  • 2-Oxobutyric acid
  • 2-Oxovaleric acid

Related Articles:

Mosquito odorant receptor for DEET and methyl jasmonate.

2014-11-18

[Proc. Natl. Acad. Sci. U. S. A. 111(46) , 16592-7, (2014)]

Kinetic resolution of 2-hydroxybutanoate racemic mixtures by NAD-independent L-lactate dehydrogenase.

2011-04-01

[Bioresour. Technol. 102(7) , 4595-9, (2011)]

Transaminase-catalyzed asymmetric synthesis of L-2-aminobutyric acid from achiral reactants.

2009-10-01

[Biotechnol. Lett. 31 , 1595-1599, (2009)]

Defect in alpha-ketobutyrate metabolism: a new inborn error.

1985-01-30

[Clin. Chim. Acta 145(2) , 173-82, (1985)]

Expanding metabolism for total biosynthesis of the nonnatural amino acid L-homoalanine.

2010-04-06

[Proc. Natl. Acad. Sci. U. S. A. 107(14) , 6234-9, (2010)]

More Articles...