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Open AccessArticle

Keratin Protein-Catalyzed Nitroaldol (Henry) Reaction and Comparison with Other Biopolymers

1
Institute of Organic Chemistry, University of Regensburg, Universitätsstr 31, Regensburg 93053, Germany
2
Institute Charles Gerhardt Montpellier-UMR 5253 CNRS/UM/ENSCM, Matériaux Avancés pour la Catalyse et la Santé, 8 rue de l'École Normale, Cedex 5, Montpellier 34296, France
3
IQAC-CSIC, Jordi Girona 18–26, Barcelona 08034, Spain
*
Author to whom correspondence should be addressed.
Academic Editor: Christophe Len
Molecules 2016, 21(9), 1122; https://doi.org/10.3390/molecules21091122
Received: 15 July 2016 / Revised: 2 August 2016 / Accepted: 2 August 2016 / Published: 25 August 2016
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 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
Keywords: keratin; biopolymer; C-C bond formation; nitroaldol reaction; Henry reaction keratin; biopolymer; C-C bond formation; nitroaldol reaction; Henry reaction
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MDPI and ACS Style

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.

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