Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases

Autores
Cuetos, Aníbal; Rioz Martínez, Ana; Bisogno, Fabricio Román; Grischek, Barbara; Lavandera, Iván; De Gonzalo, Gonzalo; Kroutil, Wolfgang; Gotor, Vicente
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
α-Alkyl-β-hydroxy esters were obtained via dynamic kinetic resolution (DKR) employing purified or crude E. coli overexpressed alcohol dehydrogenases (ADHs). ADH-A from R. ruber, CPADH from C. parapsilosis and TesADH from T. ethanolicus afforded syn-(2R,3S) derivatives with very high selectivities for sterically not impeded ketones ('small-bulky' substrates), while ADHs from S. yanoikuyae (SyADH) and Ralstonia sp. (RasADH) could also accept bulkier keto esters ('bulky-bulky' substrates). SyADH also provided preferentially syn-(2R,3S) isomers and RasADH showed in some cases good selectivity towards the formation of anti-(2S,3S) derivatives. With anti-Prelog ADHs such as LBADH from L. brevis or LKADH from L. kefir, syn-(2S,3R) alcohols were obtained with high conversions and diastereomeric excess in some cases, especially with LBADH. Furthermore, due to the thermodynamically favoured reduction of these substrates, it was possible to employ just a minimal excess of 2-propanol to obtain the final products with quantitative conversions. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fil: Cuetos, Aníbal. Universidad de Oviedo; España
Fil: Rioz Martínez, Ana. Universidad de Oviedo; España
Fil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Oviedo; España
Fil: Grischek, Barbara. University of Graz; Austria
Fil: Lavandera, Iván. Universidad de Oviedo; España
Fil: De Gonzalo, Gonzalo. Universidad de Oviedo; España
Fil: Kroutil, Wolfgang. University of Graz; Austria
Fil: Gotor, Vicente. Universidad de Oviedo; España
Materia
Β-Hydroxy Esters
Alcohol Dehydrogenases
Biocatalysis
Dynamic Kinetic Resolution
Hydrogen Transfer
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/61768
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/61768
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenasesCuetos, AníbalRioz Martínez, AnaBisogno, Fabricio RománGrischek, BarbaraLavandera, IvánDe Gonzalo, GonzaloKroutil, WolfgangGotor, VicenteΒ-Hydroxy EstersAlcohol DehydrogenasesBiocatalysisDynamic Kinetic ResolutionHydrogen Transferhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1α-Alkyl-β-hydroxy esters were obtained via dynamic kinetic resolution (DKR) employing purified or crude E. coli overexpressed alcohol dehydrogenases (ADHs). ADH-A from R. ruber, CPADH from C. parapsilosis and TesADH from T. ethanolicus afforded syn-(2R,3S) derivatives with very high selectivities for sterically not impeded ketones ('small-bulky' substrates), while ADHs from S. yanoikuyae (SyADH) and Ralstonia sp. (RasADH) could also accept bulkier keto esters ('bulky-bulky' substrates). SyADH also provided preferentially syn-(2R,3S) isomers and RasADH showed in some cases good selectivity towards the formation of anti-(2S,3S) derivatives. With anti-Prelog ADHs such as LBADH from L. brevis or LKADH from L. kefir, syn-(2S,3R) alcohols were obtained with high conversions and diastereomeric excess in some cases, especially with LBADH. Furthermore, due to the thermodynamically favoured reduction of these substrates, it was possible to employ just a minimal excess of 2-propanol to obtain the final products with quantitative conversions. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.Fil: Cuetos, Aníbal. Universidad de Oviedo; EspañaFil: Rioz Martínez, Ana. Universidad de Oviedo; EspañaFil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Oviedo; EspañaFil: Grischek, Barbara. University of Graz; AustriaFil: Lavandera, Iván. Universidad de Oviedo; EspañaFil: De Gonzalo, Gonzalo. Universidad de Oviedo; EspañaFil: Kroutil, Wolfgang. University of Graz; AustriaFil: Gotor, Vicente. Universidad de Oviedo; EspañaWiley VCH Verlag2012-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/61768Cuetos, Aníbal; Rioz Martínez, Ana; Bisogno, Fabricio Román; Grischek, Barbara; Lavandera, Iván; et al.; Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases; Wiley VCH Verlag; Advanced Synthesis & Catalysis (print); 354; 9; 6-2012; 1743-17491615-4150CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201200139info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201200139info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:35:09Zoai:ri.conicet.gov.ar:11336/61768instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-11-12 09:35:09.906CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases
title Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases
spellingShingle Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases
Cuetos, Aníbal
Β-Hydroxy Esters
Alcohol Dehydrogenases
Biocatalysis
Dynamic Kinetic Resolution
Hydrogen Transfer
title_short Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases
title_full Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases
title_fullStr Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases
title_full_unstemmed Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases
title_sort Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases
dc.creator.none.fl_str_mv Cuetos, Aníbal
Rioz Martínez, Ana
Bisogno, Fabricio Román
Grischek, Barbara
Lavandera, Iván
De Gonzalo, Gonzalo
Kroutil, Wolfgang
Gotor, Vicente
author Cuetos, Aníbal
author_facet Cuetos, Aníbal
Rioz Martínez, Ana
Bisogno, Fabricio Román
Grischek, Barbara
Lavandera, Iván
De Gonzalo, Gonzalo
Kroutil, Wolfgang
Gotor, Vicente
author_role author
author2 Rioz Martínez, Ana
Bisogno, Fabricio Román
Grischek, Barbara
Lavandera, Iván
De Gonzalo, Gonzalo
Kroutil, Wolfgang
Gotor, Vicente
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Β-Hydroxy Esters
Alcohol Dehydrogenases
Biocatalysis
Dynamic Kinetic Resolution
Hydrogen Transfer
topic Β-Hydroxy Esters
Alcohol Dehydrogenases
Biocatalysis
Dynamic Kinetic Resolution
Hydrogen Transfer
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv α-Alkyl-β-hydroxy esters were obtained via dynamic kinetic resolution (DKR) employing purified or crude E. coli overexpressed alcohol dehydrogenases (ADHs). ADH-A from R. ruber, CPADH from C. parapsilosis and TesADH from T. ethanolicus afforded syn-(2R,3S) derivatives with very high selectivities for sterically not impeded ketones ('small-bulky' substrates), while ADHs from S. yanoikuyae (SyADH) and Ralstonia sp. (RasADH) could also accept bulkier keto esters ('bulky-bulky' substrates). SyADH also provided preferentially syn-(2R,3S) isomers and RasADH showed in some cases good selectivity towards the formation of anti-(2S,3S) derivatives. With anti-Prelog ADHs such as LBADH from L. brevis or LKADH from L. kefir, syn-(2S,3R) alcohols were obtained with high conversions and diastereomeric excess in some cases, especially with LBADH. Furthermore, due to the thermodynamically favoured reduction of these substrates, it was possible to employ just a minimal excess of 2-propanol to obtain the final products with quantitative conversions. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fil: Cuetos, Aníbal. Universidad de Oviedo; España
Fil: Rioz Martínez, Ana. Universidad de Oviedo; España
Fil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Oviedo; España
Fil: Grischek, Barbara. University of Graz; Austria
Fil: Lavandera, Iván. Universidad de Oviedo; España
Fil: De Gonzalo, Gonzalo. Universidad de Oviedo; España
Fil: Kroutil, Wolfgang. University of Graz; Austria
Fil: Gotor, Vicente. Universidad de Oviedo; España
description α-Alkyl-β-hydroxy esters were obtained via dynamic kinetic resolution (DKR) employing purified or crude E. coli overexpressed alcohol dehydrogenases (ADHs). ADH-A from R. ruber, CPADH from C. parapsilosis and TesADH from T. ethanolicus afforded syn-(2R,3S) derivatives with very high selectivities for sterically not impeded ketones ('small-bulky' substrates), while ADHs from S. yanoikuyae (SyADH) and Ralstonia sp. (RasADH) could also accept bulkier keto esters ('bulky-bulky' substrates). SyADH also provided preferentially syn-(2R,3S) isomers and RasADH showed in some cases good selectivity towards the formation of anti-(2S,3S) derivatives. With anti-Prelog ADHs such as LBADH from L. brevis or LKADH from L. kefir, syn-(2S,3R) alcohols were obtained with high conversions and diastereomeric excess in some cases, especially with LBADH. Furthermore, due to the thermodynamically favoured reduction of these substrates, it was possible to employ just a minimal excess of 2-propanol to obtain the final products with quantitative conversions. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
publishDate 2012
dc.date.none.fl_str_mv 2012-06
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/61768
Cuetos, Aníbal; Rioz Martínez, Ana; Bisogno, Fabricio Román; Grischek, Barbara; Lavandera, Iván; et al.; Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases; Wiley VCH Verlag; Advanced Synthesis & Catalysis (print); 354; 9; 6-2012; 1743-1749
1615-4150
CONICET Digital
CONICET
url http://hdl.handle.net/11336/61768
identifier_str_mv Cuetos, Aníbal; Rioz Martínez, Ana; Bisogno, Fabricio Román; Grischek, Barbara; Lavandera, Iván; et al.; Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases; Wiley VCH Verlag; Advanced Synthesis & Catalysis (print); 354; 9; 6-2012; 1743-1749
1615-4150
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201200139
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201200139
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.976206

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