Cooperative effects between arginine and glutamic acid in the amino acid catalyzed aldol reaction

Abstract

Catalysis of the aldol reaction between cyclohexanone and 4-nitrobenzaldehyde by mixtures of L-Arg and of L-Glu in wet DMSO takes place with higher enantioselectivity (up to a seven-fold enhancement in the anti- aldol for the 1:1 mixture) than that observed when either L-Glu or L-Arg alone are used as the catalysts. These results can be explained by the formation of a catalytically active hydrogen-bonded complex between both amino acids, and demonstrate the possibility of positive cooperative effects in catalysis by two different α-amino acids. Chirality