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dc.contributor.author
Nigro, Mariano José
dc.contributor.author
Iribarren, Adolfo Marcelo
dc.contributor.author
Laurella, Sergio Luis
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Lewkowicz, Elizabeth Sandra
dc.date.available
2022-11-17T18:54:06Z
dc.date.issued
2018-12
dc.identifier.citation
Nigro, Mariano José; Iribarren, Adolfo Marcelo; Laurella, Sergio Luis; Lewkowicz, Elizabeth Sandra; Keto-Enol Tautomerism in Nucleobase-Substituted Aldols; Wiley Blackwell Publishing, Inc; ChemistrySelect; 3; 46; 12-2018; 13091-13097
dc.identifier.issn
2365-6549
dc.identifier.uri
http://hdl.handle.net/11336/178286
dc.description.abstract
Acyclic nucleosides, which exhibit significant antiviral activity, are usually synthesised using traditional chemical strategies. However, the efficient and selective formation of carbon-carbon bonds using small organic molecules as catalysts provides a promising alternative route for the sustainable synthesis of this family of compounds. Following this organocatalytic strategy, 5-(adenyl, thyminyl and cytosyl)-4-hydroxy-2-pentanones were prepared by the pyrrolidine catalysed reaction between the 2-oxoethyl derivative of the corresponding nucleobases and acetone. In order to investigate the keto-enol equilibrium of these compounds in basic media, H-D exchange studies were carried out by 1H and 13C NMR spectroscopy. The obtained results suggest that the mechanism by which this exchange occurs is of first order with respect to all the substrates, but of second order with regard to pyrrolidine in the case of the cytosine and adenine derivatives and of first order for the thymine analogue. Theoretical calculations of the structures involved in this equilibrium also suggest that the stability of the different ionic intermediates depends on the pKa of the corresponding nucleobases.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Wiley Blackwell Publishing, Inc
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
ACYCLIC NUCLEOSIDES
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ALDOL REACTION
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H-D EXCHANGE
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ORGANOCATALYSIS
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TAUTOMERISM
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Química Orgánica
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Keto-Enol Tautomerism in Nucleobase-Substituted Aldols
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2022-11-16T11:46:14Z
dc.journal.volume
3
dc.journal.number
46
dc.journal.pagination
13091-13097
dc.journal.pais
Alemania
dc.journal.ciudad
Weinheim
dc.description.fil
Fil: Nigro, Mariano José. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.description.fil
Fil: Iribarren, Adolfo Marcelo. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.description.fil
Fil: Laurella, Sergio Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina
dc.description.fil
Fil: Lewkowicz, Elizabeth Sandra. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología. Área Química. Laboratorio de Biotransformaciones; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.journal.title
ChemistrySelect
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/slct.201802538
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1002/slct.201802538
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