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

TitleC-C Bond formation catalyzed by natural gelatin and collagen proteins
Publication TypeJournal Article
Year of Publication2013
AuthorsKuehbeck, D, Dhar, BBijayi, Schoen, E-M, Cativiela, C, Gotor-Fernandez, V, Diaz, DDiaz
JournalBeilstein Journal of Organic Chemistry
Volume9
Pagination1111-1118
Date PublishedJUN
ISSN1860-5397
Keywordsbiocatalysis, carbon-carbon bond formation, gelatin, Henry reaction, protein
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.

DOI10.3762/bjoc.9.123
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.803

Divison category: 
Chemical Engineering & Process Development