Syntheses and catalytic actions of self-micelle-forming hydrolase models.

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Hydrolase model catalysts, N-alkyl-Nα-[2-(D-polyhydroxypentyl)-3-acetyl-4-thiazolidinylcarbonyl]-L-histidinamide (acyclic-type catalyst) and N-(N-alkanoyl-L-nistidyl)-β-D-glucosamine (cyclic-type catalyst), which easily form micelles in water by themselves, have been designed and the stereostructural effects of sugar moieties examined on stereoselective hydrolyses of p-nitrophenyl N-benzyloxycarbonyl-L-(or D-)phenylalaninates. An acyclic-type catalyst is L-selective, while a cyclic-type catalyst is L-selective. The stereorecognition of acyclictype catalysts was found to be performed by a sugar moiety, rather than the histidyl type. Comparisons of the activities of three acyclic-type catalysts having different sugar moieties show that a mannose-derived catalyst is the most stereoselective. Judging from kinetic data, it is concluded that the configuration of OH on C-3 of the sugar moiety takes a significant part in the stereorecognition of a catalyst.
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