Cyanoacrylate Inhibitors of the Hill Reaction II. Nature of the Hydrophobia Binding Domains

Abstract

A series of alkoxyalkyl-3-alkylamino-2-cyanoacrylates and related compounds have been synthesised and their Hill inhibitory activity determined in isolated pea chloroplasts. The results suggest that the alkyl group attached to the amino function interacts with a mobile lipid phase in the thylakoid membrane whilst the alkoxyalkyl group interacts with a smaller, more ordered, lipid environment. It is suggested that the former region corresponds to the interior of the lipid membrane and the latter to membrane or proteinalkyl chains in the vicinity of the membrane-protein interface. There is evidence of a localized hydrophilic pocket in the more constrained lipid environment.