Abstract
The 2-acyl-5-carboxycyclohexane-1,3-diones are plant growth retardants which are believed to act by competing with the natural co-substrate, 2-oxoglutarate, at the active site of dioxygenases involved in the later stages of the biosynthesis of the gibberellin (GA) plant hormones. A number of 2-acyl-5-carboxycyclohexanediones and related compounds were synthesized and compared with pyridine dicarboxylic acids and hydroxybenzoic acids as inhibitors of a GA 3β-hydroxylase from Cucurbita maxima endosperm. The most effective inhibitors of this enzyme possessed a 1,3-dioxo-2-acylcyclohexane-5-carboxylic acid structure. The nature of the 2-acyl group had a relatively minor effect on the potency of enzyme inhibition in vitro. A related chloro-substituted compound was shown to be a potential affinity label for this GA hydroxylase.
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