title: 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 dimethyl sulfoxide (DMSO) takes place with higher enantioselectivity (up to a 7-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 28:599-605, 2016. © 2016 Wiley Periodicals, Inc.
authors.affiliation: Departament de Química Orgànica, Universitat de Barcelona, Facultat de Química, Barcelona, Catalonia, Spain.
authors.forename: Guillem
authors.initials: G
authors.lastname: Valero
authors.affiliation: Departament de Química Orgànica, Universitat de Barcelona, Facultat de Química, Barcelona, Catalonia, Spain.
authors.forename: Albert
authors.initials: A
authors.lastname: Moyano
mesh_terms: D001120:Arginine / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D018698:Glutamic Acid / Q000737:chemistry*; D006860:Hydrogen Bonding
chemical_list: D001547:Benzaldehydes; D003512:Cyclohexanones; D018698:Glutamic Acid; C029915:4-nitrobenzaldehyde; C036468:cyclohexanone; D001120:Arginine; D004121:Dimethyl Sulfoxide
keywords: amino acids; arginine; chirality amplification; glutamic acid; organocatalysis; supramolecular catalysis