title: C-C Bond formation catalyzed by natural gelatin and collagen proteins.
abstract: 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.
authors.affiliation: Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, Regensburg 93053, Germany, Tel: + 49 941 943 4681;
authors.forename: Dennis
authors.initials: D
authors.lastname: Kühbeck
authors.forename: Basab
authors.initials: B
authors.lastname: Bijayi Dhar
authors.forename: Eva-Maria
authors.initials: EM
authors.lastname: Schön
authors.forename: Carlos
authors.initials: C
authors.lastname: Cativiela
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor-Fernández
authors.forename: David
authors.initials: D
authors.lastname: Díaz Díaz
keywords: Henry reaction; biocatalysis; carbon–carbon bond formation; gelatin; protein