TY - JOUR T1 - C-C Bond formation catalyzed by natural gelatin and collagen proteins JF - Beilstein Journal of Organic Chemistry Y1 - 2013 A1 - Kuehbeck, Dennis A1 - Dhar, Basab Bijayi A1 - Schoen, Eva-Maria A1 - Cativiela, Carlos A1 - Gotor-Fernandez, Vicente A1 - Diaz, David Diaz KW - biocatalysis KW - carbon-carbon bond formation KW - gelatin KW - Henry reaction KW - protein AB -

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.

PB - BEILSTEIN-INSTITUT CY - TRAKEHNER STRASSE 7-9, FRANKFURT AM MAIN, 60487, GERMANY VL - 9 U3 - Foreign U4 - 2.803 ER -