Issue 10, 1997

Supramolecular catalysis of H/D exchange in pyruvate by macrocyclic polyamines involving a reactive iminium intermediate

Abstract

The activity of a series of macrocyclic polyamines as catalysts for proton exchange has been investigated. Structural and physico-chemical studies demonstrate the ability of these receptors to recognize pyruvate, form a covalent iminium intermediate and catalyse H/D exchange at the CH3 position. The reaction follows Michaelis–Menten kinetics with a rate enhancement higher than 4.8 × 105 (kcat/kuncat). The process also represents a potential entry into the catalysis of aldol condensation reactions.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1997, 2073-2081

Supramolecular catalysis of H/D exchange in pyruvate by macrocyclic polyamines involving a reactive iminium intermediate

H. Fenniri, C. Dallaire, D. P. Funeriu and J. Lehn, J. Chem. Soc., Perkin Trans. 2, 1997, 2073 DOI: 10.1039/A700937B

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