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2005
Carboxylic acid esters
P 0360
Two New Irreversible Inhibitors of Dihydrodipicolinate Synthase: Diethyl
and Diethyl (E)-4-Oxo-2-heptenedioate. —
25- 061 (E,E)-4-Oxo-2,5-heptadienedioate
According to a literature procedure, diethyl oxoheptadienedioate (V) is synthesized
in excellent yield. Diethyl oxoheptenedioate (III) is prepared following a modification
of this method. In accordance with the postulated mechanism, unsaturated ketones (III)
and (V) exhibit time-dependent irreversible inhibition. Alkene (III) is only a weak inhibitor, whereas diene (V) is active at micromolar concentrations. Compounds (III) and
(V) are designed to mimic the acyclic enzyme-bound condensation product of
(S)-aspartate semialdehyde and pyruvate and represent an important new lead in the
design of potent inhibitors for the title enzyme. — (TURNER, J. J.; HEALY, J. P.;
DOBSON, R. C. J.; GERRARD, J. A.; HUTTON*, C. A.; Bioorg. Med. Chem. Lett.
15 (2005) 4, 995-998; Sch. Chem., Univ. N. S. W., Sydney, N. S. W. 2006, Australia;
Eng.) — H. Hoennerscheid
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