Enantioselective preparation of delta-valerolactones using horse liver alcohol dehydrogenase

Horse liver alcohol dehydrogenase (HLADH) has been found to be a versatile biocatalyst for the desymmetrization of prochiral 3‐arylpentane‐1,5‐diols, based on a two‐step one‐pot oxidation. This procedure has allowed the formation of valuable (S)‐lactones in good to excellent conversions and enantiom...

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Detalles Bibliográficos
Autores: Díaz-Rodríguez, Alba, Iglesias-Fernández, Javier, Rovira i Virgili, Carme, Gotor-Fernández, Vicente
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2013
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/125021
Acceso en línea:https://hdl.handle.net/2445/125021
Access Level:acceso abierto
Palabra clave:Biocatàlisi
Síntesi asimètrica
Biocatalysis
Asymmetric synthesis
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spelling Enantioselective preparation of delta-valerolactones using horse liver alcohol dehydrogenaseDíaz-Rodríguez, AlbaIglesias-Fernández, JavierRovira i Virgili, CarmeGotor-Fernández, VicenteBiocatàlisiSíntesi asimètricaBiocatalysisAsymmetric synthesisHorse liver alcohol dehydrogenase (HLADH) has been found to be a versatile biocatalyst for the desymmetrization of prochiral 3‐arylpentane‐1,5‐diols, based on a two‐step one‐pot oxidation. This procedure has allowed the formation of valuable (S)‐lactones in good to excellent conversions and enantiomeric excess. The catalytic performance of HLADH has been studied using several cofactor regeneration systems and cosolvents, finding great improvements in terms of activity with L‐lactate dehydrogenase, while the stereoselectivity of the process was significantly improved when using tetrahydrofuran. Docking studies has revealed the pattern substitution importance in the selectivity and activity of this oxidative processWiley-VCH2018201820132018info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion5 p.application/pdfhttps://hdl.handle.net/2445/125021Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésVersió postprint del document publicat a: https://doi.org/10.1002/cctc.201300640ChemCatChem, 2013, vol. 6, num. 4, p. 977-980https://doi.org/10.1002/cctc.201300640info:eu-repo/grantAgreement/EC/FP7/266025(c) Wiley-VCH, 2013info:eu-repo/semantics/openAccessoai:recercat.cat:2445/1250212026-05-29T05:05:01Z
dc.title.none.fl_str_mv Enantioselective preparation of delta-valerolactones using horse liver alcohol dehydrogenase
title Enantioselective preparation of delta-valerolactones using horse liver alcohol dehydrogenase
spellingShingle Enantioselective preparation of delta-valerolactones using horse liver alcohol dehydrogenase
Díaz-Rodríguez, Alba
Biocatàlisi
Síntesi asimètrica
Biocatalysis
Asymmetric synthesis
title_short Enantioselective preparation of delta-valerolactones using horse liver alcohol dehydrogenase
title_full Enantioselective preparation of delta-valerolactones using horse liver alcohol dehydrogenase
title_fullStr Enantioselective preparation of delta-valerolactones using horse liver alcohol dehydrogenase
title_full_unstemmed Enantioselective preparation of delta-valerolactones using horse liver alcohol dehydrogenase
title_sort Enantioselective preparation of delta-valerolactones using horse liver alcohol dehydrogenase
dc.creator.none.fl_str_mv Díaz-Rodríguez, Alba
Iglesias-Fernández, Javier
Rovira i Virgili, Carme
Gotor-Fernández, Vicente
author Díaz-Rodríguez, Alba
author_facet Díaz-Rodríguez, Alba
Iglesias-Fernández, Javier
Rovira i Virgili, Carme
Gotor-Fernández, Vicente
author_role author
author2 Iglesias-Fernández, Javier
Rovira i Virgili, Carme
Gotor-Fernández, Vicente
author2_role author
author
author
dc.subject.none.fl_str_mv Biocatàlisi
Síntesi asimètrica
Biocatalysis
Asymmetric synthesis
topic Biocatàlisi
Síntesi asimètrica
Biocatalysis
Asymmetric synthesis
description Horse liver alcohol dehydrogenase (HLADH) has been found to be a versatile biocatalyst for the desymmetrization of prochiral 3‐arylpentane‐1,5‐diols, based on a two‐step one‐pot oxidation. This procedure has allowed the formation of valuable (S)‐lactones in good to excellent conversions and enantiomeric excess. The catalytic performance of HLADH has been studied using several cofactor regeneration systems and cosolvents, finding great improvements in terms of activity with L‐lactate dehydrogenase, while the stereoselectivity of the process was significantly improved when using tetrahydrofuran. Docking studies has revealed the pattern substitution importance in the selectivity and activity of this oxidative process
publishDate 2013
dc.date.none.fl_str_mv 2013
2018
2018
2018
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/125021
url https://hdl.handle.net/2445/125021
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1002/cctc.201300640
ChemCatChem, 2013, vol. 6, num. 4, p. 977-980
https://doi.org/10.1002/cctc.201300640
info:eu-repo/grantAgreement/EC/FP7/266025
dc.rights.none.fl_str_mv (c) Wiley-VCH, 2013
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Wiley-VCH, 2013
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 5 p.
application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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