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

Beilstein Journal of Organic Chemistry

Vicente Gotor-Fernández¹  Basab Bijayi Dhar¹  Eva-Maria Schön²  Dennis Kühbeck³  Carlos Cativiela³  David Díaz Díaz⁴ 

[1] Fax: + 49 941 943 4121;CReST Unit, Chemical Engineering Div., National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India;Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, Regensburg 93053, Germany, Tel: + 49 941 943 4681;Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza-CSIC, Pedro Cerbuna s/n, Zaragoza 50009, Spain;

关键词: biocatalysis;    carbon–carbon bond formation;    gelatin;    Henry reaction;    protein;   

DOI  :  10.3762/bjoc.9.123

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown