DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems

In this manuscript we report a critical evaluation of the ability of natural DNA to mediate the nitroaldol (Henry) reaction at physiological temperature in pure water. Under these conditions, no background reaction took place (i.e., control experiment without DNA). Both heteroaromatic aldehydes (e.g...

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Detalles Bibliográficos
Autores: Häring, Marleen, Pérez-Madrigal, María M., Kühbeck, Dennis, Pettignano, Asja, Quignard, Françoise
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2015
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/130258
Acceso en línea:http://hdl.handle.net/10261/130258
Access Level:acceso abierto
Palabra clave:Buffer solutions
DNA
C-C bond formation
Henry reaction
Nitroaldol reaction
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spelling DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer SystemsHäring, MarleenPérez-Madrigal, María M.Kühbeck, DennisPettignano, AsjaQuignard, FrançoiseBuffer solutionsDNAC-C bond formationHenry reactionNitroaldol reactionIn this manuscript we report a critical evaluation of the ability of natural DNA to mediate the nitroaldol (Henry) reaction at physiological temperature in pure water. Under these conditions, no background reaction took place (i.e., control experiment without DNA). Both heteroaromatic aldehydes (e.g., 2-pyridinecarboxaldehyde) and aromatic aldehydes bearing strong or moderate electron-withdrawing groups reacted satisfactorily with nitromethane obeying first order kinetics and affording the corresponding β-nitroalcohols in good yields within 24 h. In contrast, aliphatic aldehydes and aromatic aldehydes having electron-donating groups either did not react or were poorly converted. Moreover, we discovered that a number of metal-free organic buffers efficiently promote the Henry reaction when they were used as reaction media without adding external catalysts. This constitutes an important observation because the influence of organic buffers in chemical processes has been traditionally underestimatedFinancial assistant by Universität Regensburg and SINCHEM Program (Erasmus Mundus Action 1 FPA 2013-0037) are gratefully acknowledged. D.D.D. thanks J.J. Marrero-Tellado for helpful discussions and DFG for the Heisenberg Professorship Award.Peer reviewedMultidisciplinary Digital Publishing InstituteConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201620162015info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/130258reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttp://dx.doi.org/10.1155/2013/631875/10.3390/molecules20034136Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1302582026-05-22T06:33:51Z
dc.title.none.fl_str_mv DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems
title DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems
spellingShingle DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems
Häring, Marleen
Buffer solutions
DNA
C-C bond formation
Henry reaction
Nitroaldol reaction
title_short DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems
title_full DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems
title_fullStr DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems
title_full_unstemmed DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems
title_sort DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems
dc.creator.none.fl_str_mv Häring, Marleen
Pérez-Madrigal, María M.
Kühbeck, Dennis
Pettignano, Asja
Quignard, Françoise
author Häring, Marleen
author_facet Häring, Marleen
Pérez-Madrigal, María M.
Kühbeck, Dennis
Pettignano, Asja
Quignard, Françoise
author_role author
author2 Pérez-Madrigal, María M.
Kühbeck, Dennis
Pettignano, Asja
Quignard, Françoise
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Buffer solutions
DNA
C-C bond formation
Henry reaction
Nitroaldol reaction
topic Buffer solutions
DNA
C-C bond formation
Henry reaction
Nitroaldol reaction
description In this manuscript we report a critical evaluation of the ability of natural DNA to mediate the nitroaldol (Henry) reaction at physiological temperature in pure water. Under these conditions, no background reaction took place (i.e., control experiment without DNA). Both heteroaromatic aldehydes (e.g., 2-pyridinecarboxaldehyde) and aromatic aldehydes bearing strong or moderate electron-withdrawing groups reacted satisfactorily with nitromethane obeying first order kinetics and affording the corresponding β-nitroalcohols in good yields within 24 h. In contrast, aliphatic aldehydes and aromatic aldehydes having electron-donating groups either did not react or were poorly converted. Moreover, we discovered that a number of metal-free organic buffers efficiently promote the Henry reaction when they were used as reaction media without adding external catalysts. This constitutes an important observation because the influence of organic buffers in chemical processes has been traditionally underestimated
publishDate 2015
dc.date.none.fl_str_mv 2015
2016
2016
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/10261/130258
url http://hdl.handle.net/10261/130258
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv http://dx.doi.org/10.1155/2013/631875/10.3390/molecules20034136
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
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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