Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation

Autores
Decarlini, Maria Florencia; Bordon, Daniela Laura; Vázquez, Ana M.; Demmel, Gabriela Ines; Rossi, Laura Isabel; Aimar, Mario Leandro
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A mechanistic interpretation of the kinetic profiles obtained for the stereoselective reduction of acetophenone promoted by Galactomyces candidus GZ1 under aerobic and anaerobic conditions was made. Based on experimental and bibliographical data, a mechanism which may involve the participation of two alcohol dehydrogenases with opposite stereoselectivities and alcohol oxidase is discussed. Due to the stereoselectivity of the reduction of acetophenone being changed when anaerobic conditions were used, this microorganism also permitted (S)-1-phenylethanol to be obtained in the absence of oxygen. Moreover, the kinetic profiles of the reactions of a racemic mixture of (R,S)-1-phenylethanol and pure (S)-1-phenylethanol with Gal. candidus were analyzed, which corroborated that there existed a reaction step where (S)-1-phenylethanol was oxidized to acetophenone. The results presented here show that not only is it possible to resolve racemic mixtures of phenylethanols when Gal. candidus is used as a biocatalyst, but that this is also efficient in causing the complete stereoinversion of pure (S)-1-phenylethanol to (R)-1-phenylethanol.
Fil: Decarlini, Maria Florencia. Universidad Católica de Córdoba; Argentina
Fil: Bordon, Daniela Laura. Universidad Nacional de Córdoba; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Vázquez, Ana M.. Universidad Católica de Córdoba; Argentina
Fil: Demmel, Gabriela Ines. Universidad Católica de Córdoba; Argentina
Fil: Rossi, Laura Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Aimar, Mario Leandro. Universidad Nacional de Córdoba; Argentina
Materia
1-PHENYLETHANOL
BIOCATALYSIS
DERACEMIZATION
GALACTOMYCES CANDIDUS
STEREOINVERSION
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:11336/124434
Acceder
id CONICETDig_2f890e29d38e8a271719f12ee152a94e
oai_identifier_str oai:ri.conicet.gov.ar:11336/124434
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretationDecarlini, Maria FlorenciaBordon, Daniela LauraVázquez, Ana M.Demmel, Gabriela InesRossi, Laura IsabelAimar, Mario Leandro1-PHENYLETHANOLBIOCATALYSISDERACEMIZATIONGALACTOMYCES CANDIDUSSTEREOINVERSIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A mechanistic interpretation of the kinetic profiles obtained for the stereoselective reduction of acetophenone promoted by Galactomyces candidus GZ1 under aerobic and anaerobic conditions was made. Based on experimental and bibliographical data, a mechanism which may involve the participation of two alcohol dehydrogenases with opposite stereoselectivities and alcohol oxidase is discussed. Due to the stereoselectivity of the reduction of acetophenone being changed when anaerobic conditions were used, this microorganism also permitted (S)-1-phenylethanol to be obtained in the absence of oxygen. Moreover, the kinetic profiles of the reactions of a racemic mixture of (R,S)-1-phenylethanol and pure (S)-1-phenylethanol with Gal. candidus were analyzed, which corroborated that there existed a reaction step where (S)-1-phenylethanol was oxidized to acetophenone. The results presented here show that not only is it possible to resolve racemic mixtures of phenylethanols when Gal. candidus is used as a biocatalyst, but that this is also efficient in causing the complete stereoinversion of pure (S)-1-phenylethanol to (R)-1-phenylethanol.Fil: Decarlini, Maria Florencia. Universidad Católica de Córdoba; ArgentinaFil: Bordon, Daniela Laura. Universidad Nacional de Córdoba; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Vázquez, Ana M.. Universidad Católica de Córdoba; ArgentinaFil: Demmel, Gabriela Ines. Universidad Católica de Córdoba; ArgentinaFil: Rossi, Laura Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Aimar, Mario Leandro. Universidad Nacional de Córdoba; ArgentinaElsevier2019-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/124434Decarlini, Maria Florencia; Bordon, Daniela Laura; Vázquez, Ana M.; Demmel, Gabriela Ines; Rossi, Laura Isabel; et al.; Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation; Elsevier; Biocatalysis and Agricultural Biotechnology; 17; 1-2019; 7-141878-8181CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S1878818118303992info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bcab.2018.10.010info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:59:32Zoai:ri.conicet.gov.ar:11336/124434instacron: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:34982025-09-03 09:59:32.954CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation
title Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation
spellingShingle Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation
Decarlini, Maria Florencia
1-PHENYLETHANOL
BIOCATALYSIS
DERACEMIZATION
GALACTOMYCES CANDIDUS
STEREOINVERSION
title_short Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation
title_full Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation
title_fullStr Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation
title_full_unstemmed Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation
title_sort Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation
dc.creator.none.fl_str_mv Decarlini, Maria Florencia
Bordon, Daniela Laura
Vázquez, Ana M.
Demmel, Gabriela Ines
Rossi, Laura Isabel
Aimar, Mario Leandro
author Decarlini, Maria Florencia
author_facet Decarlini, Maria Florencia
Bordon, Daniela Laura
Vázquez, Ana M.
Demmel, Gabriela Ines
Rossi, Laura Isabel
Aimar, Mario Leandro
author_role author
author2 Bordon, Daniela Laura
Vázquez, Ana M.
Demmel, Gabriela Ines
Rossi, Laura Isabel
Aimar, Mario Leandro
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv 1-PHENYLETHANOL
BIOCATALYSIS
DERACEMIZATION
GALACTOMYCES CANDIDUS
STEREOINVERSION
topic 1-PHENYLETHANOL
BIOCATALYSIS
DERACEMIZATION
GALACTOMYCES CANDIDUS
STEREOINVERSION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A mechanistic interpretation of the kinetic profiles obtained for the stereoselective reduction of acetophenone promoted by Galactomyces candidus GZ1 under aerobic and anaerobic conditions was made. Based on experimental and bibliographical data, a mechanism which may involve the participation of two alcohol dehydrogenases with opposite stereoselectivities and alcohol oxidase is discussed. Due to the stereoselectivity of the reduction of acetophenone being changed when anaerobic conditions were used, this microorganism also permitted (S)-1-phenylethanol to be obtained in the absence of oxygen. Moreover, the kinetic profiles of the reactions of a racemic mixture of (R,S)-1-phenylethanol and pure (S)-1-phenylethanol with Gal. candidus were analyzed, which corroborated that there existed a reaction step where (S)-1-phenylethanol was oxidized to acetophenone. The results presented here show that not only is it possible to resolve racemic mixtures of phenylethanols when Gal. candidus is used as a biocatalyst, but that this is also efficient in causing the complete stereoinversion of pure (S)-1-phenylethanol to (R)-1-phenylethanol.
Fil: Decarlini, Maria Florencia. Universidad Católica de Córdoba; Argentina
Fil: Bordon, Daniela Laura. Universidad Nacional de Córdoba; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Vázquez, Ana M.. Universidad Católica de Córdoba; Argentina
Fil: Demmel, Gabriela Ines. Universidad Católica de Córdoba; Argentina
Fil: Rossi, Laura Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Aimar, Mario Leandro. Universidad Nacional de Córdoba; Argentina
description A mechanistic interpretation of the kinetic profiles obtained for the stereoselective reduction of acetophenone promoted by Galactomyces candidus GZ1 under aerobic and anaerobic conditions was made. Based on experimental and bibliographical data, a mechanism which may involve the participation of two alcohol dehydrogenases with opposite stereoselectivities and alcohol oxidase is discussed. Due to the stereoselectivity of the reduction of acetophenone being changed when anaerobic conditions were used, this microorganism also permitted (S)-1-phenylethanol to be obtained in the absence of oxygen. Moreover, the kinetic profiles of the reactions of a racemic mixture of (R,S)-1-phenylethanol and pure (S)-1-phenylethanol with Gal. candidus were analyzed, which corroborated that there existed a reaction step where (S)-1-phenylethanol was oxidized to acetophenone. The results presented here show that not only is it possible to resolve racemic mixtures of phenylethanols when Gal. candidus is used as a biocatalyst, but that this is also efficient in causing the complete stereoinversion of pure (S)-1-phenylethanol to (R)-1-phenylethanol.
publishDate 2019
dc.date.none.fl_str_mv 2019-01
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/11336/124434
Decarlini, Maria Florencia; Bordon, Daniela Laura; Vázquez, Ana M.; Demmel, Gabriela Ines; Rossi, Laura Isabel; et al.; Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation; Elsevier; Biocatalysis and Agricultural Biotechnology; 17; 1-2019; 7-14
1878-8181
CONICET Digital
CONICET
url http://hdl.handle.net/11336/124434
identifier_str_mv Decarlini, Maria Florencia; Bordon, Daniela Laura; Vázquez, Ana M.; Demmel, Gabriela Ines; Rossi, Laura Isabel; et al.; Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation; Elsevier; Biocatalysis and Agricultural Biotechnology; 17; 1-2019; 7-14
1878-8181
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S1878818118303992
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bcab.2018.10.010
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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
_version_ 1842269586474401792
score 12.885934

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