Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains

Autores
Sortino, Maximiliano Andrés; Cechinel Filho, Valdir; Zacchino, Susana Alicia Stella
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The CAC double bond of non-substituted and substituted maleimides were hydrogenated to the corresponding succinimides by fungal strains. 2- and 2,3-methylated-phenyl-maleimides were enantioselectively reduced to (R)-N-phenyl-3-methylsuccinimide and to trans-(R,R)-N-phenyl-2,3-dimethylsuccinimide respectively by Aspergillus niger, A. flavus and A. fumigatus (conversion 96 to 99%), Fusarium graminearum and Penicillium sp (conversion: 37 and 39%), with 99% ee.
Fil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Cechinel Filho, Valdir. University of the Itajaí Valley; Brasil
Fil: Zacchino, Susana Alicia Stella. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Materia
enantioselective reduction
Biotransformation
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:11336/130936
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strainsSortino, Maximiliano AndrésCechinel Filho, ValdirZacchino, Susana Alicia Stellaenantioselective reductionBiotransformationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The CAC double bond of non-substituted and substituted maleimides were hydrogenated to the corresponding succinimides by fungal strains. 2- and 2,3-methylated-phenyl-maleimides were enantioselectively reduced to (R)-N-phenyl-3-methylsuccinimide and to trans-(R,R)-N-phenyl-2,3-dimethylsuccinimide respectively by Aspergillus niger, A. flavus and A. fumigatus (conversion 96 to 99%), Fusarium graminearum and Penicillium sp (conversion: 37 and 39%), with 99% ee.Fil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Cechinel Filho, Valdir. University of the Itajaí Valley; BrasilFil: Zacchino, Susana Alicia Stella. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaPergamon-Elsevier Science Ltd2009-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/130936Sortino, Maximiliano Andrés; Cechinel Filho, Valdir; Zacchino, Susana Alicia Stella; Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 20; 5-2009; 1106-11080957-4166CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0957416609003255?via%3Dihubinfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2009.04.009info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:54:07Zoai:ri.conicet.gov.ar:11336/130936instacron: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 09:54:07.446CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains
title Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains
spellingShingle Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains
Sortino, Maximiliano Andrés
enantioselective reduction
Biotransformation
title_short Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains
title_full Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains
title_fullStr Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains
title_full_unstemmed Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains
title_sort Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains
dc.creator.none.fl_str_mv Sortino, Maximiliano Andrés
Cechinel Filho, Valdir
Zacchino, Susana Alicia Stella
author Sortino, Maximiliano Andrés
author_facet Sortino, Maximiliano Andrés
Cechinel Filho, Valdir
Zacchino, Susana Alicia Stella
author_role author
author2 Cechinel Filho, Valdir
Zacchino, Susana Alicia Stella
author2_role author
author
dc.subject.none.fl_str_mv enantioselective reduction
Biotransformation
topic enantioselective reduction
Biotransformation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The CAC double bond of non-substituted and substituted maleimides were hydrogenated to the corresponding succinimides by fungal strains. 2- and 2,3-methylated-phenyl-maleimides were enantioselectively reduced to (R)-N-phenyl-3-methylsuccinimide and to trans-(R,R)-N-phenyl-2,3-dimethylsuccinimide respectively by Aspergillus niger, A. flavus and A. fumigatus (conversion 96 to 99%), Fusarium graminearum and Penicillium sp (conversion: 37 and 39%), with 99% ee.
Fil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Cechinel Filho, Valdir. University of the Itajaí Valley; Brasil
Fil: Zacchino, Susana Alicia Stella. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
description The CAC double bond of non-substituted and substituted maleimides were hydrogenated to the corresponding succinimides by fungal strains. 2- and 2,3-methylated-phenyl-maleimides were enantioselectively reduced to (R)-N-phenyl-3-methylsuccinimide and to trans-(R,R)-N-phenyl-2,3-dimethylsuccinimide respectively by Aspergillus niger, A. flavus and A. fumigatus (conversion 96 to 99%), Fusarium graminearum and Penicillium sp (conversion: 37 and 39%), with 99% ee.
publishDate 2009
dc.date.none.fl_str_mv 2009-05
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/11336/130936
Sortino, Maximiliano Andrés; Cechinel Filho, Valdir; Zacchino, Susana Alicia Stella; Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 20; 5-2009; 1106-1108
0957-4166
CONICET Digital
CONICET
url http://hdl.handle.net/11336/130936
identifier_str_mv Sortino, Maximiliano Andrés; Cechinel Filho, Valdir; Zacchino, Susana Alicia Stella; Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl-maleimides by fungal strains; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 20; 5-2009; 1106-1108
0957-4166
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/S0957416609003255?via%3Dihub
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2009.04.009
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
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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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