Keratin Protein-Catalyzed Nitroaldol (Henry) Reaction and Comparison with Other Biopolymers
AbstractHere 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 β-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. View Full-Text
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Häring, M.; Pettignano, A.; Quignard, F.; Tanchoux, N.; Díaz Díaz, D. Keratin Protein-Catalyzed Nitroaldol (Henry) Reaction and Comparison with Other Biopolymers. Molecules 2016, 21, 1122.
Häring M, Pettignano A, Quignard F, Tanchoux N, Díaz Díaz D. Keratin Protein-Catalyzed Nitroaldol (Henry) Reaction and Comparison with Other Biopolymers. Molecules. 2016; 21(9):1122.Chicago/Turabian Style
Häring, Marleen; Pettignano, Asja; Quignard, Françoise; Tanchoux, Nathalie; Díaz Díaz, David. 2016. "Keratin Protein-Catalyzed Nitroaldol (Henry) Reaction and Comparison with Other Biopolymers." Molecules 21, no. 9: 1122.
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