Haering, Marleen and Pettignano, Asja and Quignard, Francoise and Tanchoux, Nathalie and Diaz Diaz, David (2016) Keratin Protein-Catalyzed Nitroaldol (Henry) Reaction and Comparison with Other Biopolymers. MOLECULES, 21 (9): 1122. ISSN 1420-3049,
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Here we describe a preliminary investigation on the ability of natural keratin to catalyze the nitroaldol (Henry) reaction between aldehydes and nitroalkanes. Both aromatic and heteroaromatic aldehydes bearing strong or moderate electron-withdrawing groups were converted into the corresponding -nitroalcohol products in both DMSO and in water in the presence of tetrabutylammonium bromide (TBAB) as a phase transfer catalyst. Negligible background reactions (i.e., negative control experiment in the absence of keratin protein) were observed in these solvent systems. Aromatic aldehydes bearing electron-donating groups and aliphatic aldehydes showed poor or no conversion, respectively. In general, the reactions in water/TBAB required twice the amount of time than in DMSO to achieve similar conversions. Moreover, comparison of the kinetics of the keratin-mediated nitroaldol (Henry) reaction with other biopolymers revealed slower rates for the former and the possibility of fine-tuning the kinetics by appropriate selection of the biopolymer and solvent.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | C BOND FORMATION; BIOMATERIALS; FILAMENTS; SEQUENCE; keratin; biopolymer; C-C bond formation; nitroaldol reaction; Henry reaction |
| 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: | 03 Apr 2019 13:35 |
| Last Modified: | 03 Apr 2019 13:35 |
| URI: | https://pred.uni-regensburg.de/id/eprint/3373 |
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