Key result
The coenzyme A thioester of (methylenecyclopropyl)acetic acid inactivates acyl dehydrogenases, whereas the coenzyme A thioester of β-(cyclopropylidene) propionic acid does not.
The study demonstrates disparate reactivity and enzyme inactivation properties between thioesters of (methylenecyclopropyl)acetic acid and β-(cyclopropylidene)propionic acid.
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Differential thioester effects warrant no clinical translation; leaves open cyclopropyl-specific mechanisms of acyl dehydrogenase inactivation.
The anion generated from the isopropyl thioester of (methylenecyclopropyl)acetic acid may be quenched with water to give an unrearranged thioester and an acyclic isomer, isopropyl 4-methylpenta-2E,4-dienethioate; the coenzyme A thioester of (methylenecyclopropyl)acetic acid is a known inactivator of acyl dehydrogenases. The isopropyl thioester of β-(cyclopropylidene) propionic acid reacts with LDA followed by water to give only 3-(cyclopropyl)prop-2E-enethioate, and its coenzyme A thioester does not inactivate the acyl dehydrogenase from pig kidney (EC 1.3.99.3).
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Baldwin et al. (1990) studied this question. Thioesters of (methylenecyclopropyl)acetic and β-(cyclopropylidene)propionic acids was evaluated on Reaction products with lithium diisopropylamide and inactivation of acyl dehydrogenase. The coenzyme A thioester of (methylenecyclopropyl)acetic acid inactivates acyl dehydrogenases, whereas the coenzyme A thioester of β-(cyclopropylidene) propionic acid does not.
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