C-C Bond formation catalyzed by natural gelatin and collagen proteins

The activity of gelatin and collagen proteins towards C–C bond formation via Henry (nitroaldol) reaction between aldehydes and nitroalkanes is demonstrated for the first time. Among other variables, protein source, physical state and chemical modification influence product yield and kinetics, affording the nitroaldol products in both aqueous and organic media under mild conditions. Significantly, the scale-up of the process between 4-nitrobenzaldehyde and nitromethane is successfully achieved at 1 g scale and in good yield. A comparative kinetic study with other biocatalysts shows an increase of the first-order rate constant in the order chitosan < gelatin < bovine serum albumin (BSA) < collagen. The results of this study indicate that simple edible gelatin can promote C–C bond forming reactions under physiological conditions, which may have important implications from a metabolic perspective

C-C Bond formation catalyzed by natural gelatin and collagen proteins

This is an Open Access article under the terms of the Creative Commons Attribution License.The activity of gelatin and collagen proteins towards C-C bond formation via Henry (nitroaldol) reaction between aldehydes and nitroalkanes is demonstrated for the first time. Among other variables, protein source, physical state and chemical modification influence product yield and kinetics, affording the nitroaldol products in both aqueous and organic media under mild conditions. Significantly, the scale-up of the process between 4-nitrobenzaldehyde and nitromethane is successfully achieved at 1 g scale and in good yield. A comparative kinetic study with other biocatalysts shows an increase of the first-order rate constant in the order chitosan < gelatin < bovine serum albumin (BSA) < collagen. The results of this study indicate that simple edible gelatin can promote C-C bond forming reactions under physiological conditions, which may have important implications from a metabolic perspective. © 2013 Kühbeck et al; licensee Beilstein-Institut.This work was supported by the Universität Regensburg (Förderlinie C des Finanziellen Anreizsystems für Drittmitteleinwerbung), Ministerio de Ciencia e Innovación – FEDER (CTQ2010-17436), Gobierno de Aragón-FSE (research group E40). B.B.D. thanks CSIR for appointment as a Sr Research Associate (Scientist’s Pool Scheme).Peer Reviewe