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

AuthorsKühbeck, Dennis; Bijayi Dhar, Basab; Schön, Eva-Maria; Cativiela, Carlos ; Gotor-Fernández, Vicente; Díaz Díaz, David
Henry reaction
Carbon–carbon bond formation
Issue Date2013
PublisherBeilstein-Institut für Literatur der Organischen Chemie
CitationBeilstein Journal of Organic Chemistry 9: 1111-1118 (2013)
AbstractThe 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.
DescriptionThis is an Open Access article under the terms of the Creative Commons Attribution License.
Publisher version (URL)http://dx.doi.org/10.3762/bjoc.9.123
Identifiersdoi: 10.3762/bjoc.9.123
issn: 1860-5397
Appears in Collections:(ISQCH) Artículos
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