Substrate-selective mechanisms in biocatalysis demonstrated with a versatile and efficient aldolase antibody.
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.
Shulman
H
H
Department of Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa.
Keinan
E
E
D017151:Antibodies, Catalytic / Q000737:chemistry*; D005634:Fructose-Bisphosphate Aldolase / Q000737:chemistry* / Q000276:immunology*; D007700:Kinetics; D008956:Models, Chemical; D012545:Schiff Bases; D013329:Structure-Activity Relationship
D017151:Antibodies, Catalytic; D012545:Schiff Bases; D005634:Fructose-Bisphosphate Aldolase