Substrate-selective mechanisms in biocatalysis demonstrated with a versatile and efficient aldolase antibody

Article abstract of DOI:10.1016/S0960-894X(99)00292-9

A structure-activity relationship study with a series of aldol substrates shows that the mechanism of the antibody 38C2-catalyzed retrograde aldol reaction depends on the nature of the substrate with electron-deficient substrates an early deprotonation precedes the C-C bond cleavage while with electron-rich substrates the catalytic mechanism involves an initial C-C bond cleavage leading to a positively charged intermediate.