Kuehbeck, Dennis and Dhar, Basab Bijayi and Schoen, Eva-Maria and Cativiela, Carlos and Gotor-Fernandez, Vicente and Diaz Diaz, David (2013) C-C Bond formation catalyzed by natural gelatin and collagen proteins. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 9. pp. 1111-1118. ISSN 1860-5397,
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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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ASYMMETRIC ALDOL REACTION; ACYCLIC AMINO-ACIDS; ORGANIC-SYNTHESIS; HENRY REACTION; PROMISCUITY; biocatalysis; carbon-carbon bond formation; gelatin; Henry reaction; protein |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. David Díaz Díaz |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 07 Apr 2020 12:07 |
| Last Modified: | 07 Apr 2020 12:07 |
| URI: | https://pred.uni-regensburg.de/id/eprint/16516 |
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