Keratin protein-catalyzed nitroaldol (henry) reaction and comparison with other biopolymers

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-nit...

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Detalhes bibliográficos
Autores: Häring, Marleen, Díaz Díaz, David
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2016
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/177702
Acesso em linha:http://hdl.handle.net/10261/177702
Access Level:acceso abierto
Palavra-chave:Enantioselectivity
Ligands
Nitroaldol reaction
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spelling Keratin protein-catalyzed nitroaldol (henry) reaction and comparison with other biopolymersHäring, MarleenDíaz Díaz, DavidEnantioselectivityLigandsNitroaldol reactionHere 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. © 2016 by the authors; licensee MDPI, Basel, Switzerland.D.D.D. thanks the Deutsche Forschungsgemeinschaft (DFG) for the Heisenberg Professorship Award. A.P. thanks the SINCHEM program for her PhD Grant. SINCHEM is a Joint Doctorate program selected under the Erasmus Mundus Action 1 Program—FPA 2013-0037.Peer reviewedMolecular Diversity Preservation InternationalConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201920192016info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/177702reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttps://doi.org/10.3390/molecules21091122Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1777022026-05-22T06:33:51Z
dc.title.none.fl_str_mv Keratin protein-catalyzed nitroaldol (henry) reaction and comparison with other biopolymers
title Keratin protein-catalyzed nitroaldol (henry) reaction and comparison with other biopolymers
spellingShingle Keratin protein-catalyzed nitroaldol (henry) reaction and comparison with other biopolymers
Häring, Marleen
Enantioselectivity
Ligands
Nitroaldol reaction
title_short Keratin protein-catalyzed nitroaldol (henry) reaction and comparison with other biopolymers
title_full Keratin protein-catalyzed nitroaldol (henry) reaction and comparison with other biopolymers
title_fullStr Keratin protein-catalyzed nitroaldol (henry) reaction and comparison with other biopolymers
title_full_unstemmed Keratin protein-catalyzed nitroaldol (henry) reaction and comparison with other biopolymers
title_sort Keratin protein-catalyzed nitroaldol (henry) reaction and comparison with other biopolymers
dc.creator.none.fl_str_mv Häring, Marleen
Díaz Díaz, David
author Häring, Marleen
author_facet Häring, Marleen
Díaz Díaz, David
author_role author
author2 Díaz Díaz, David
author2_role author
dc.contributor.none.fl_str_mv Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Enantioselectivity
Ligands
Nitroaldol reaction
topic Enantioselectivity
Ligands
Nitroaldol reaction
description 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. © 2016 by the authors; licensee MDPI, Basel, Switzerland.
publishDate 2016
dc.date.none.fl_str_mv 2016
2019
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/177702
url http://hdl.handle.net/10261/177702
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://doi.org/10.3390/molecules21091122
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.812429

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