Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives

Autores
Orden, Alejandro Agustin; Schrittwieser, Joerg H.; Resch, Verena; Mutti, Francesco G.; Kroutil, Wolfgang
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A chemoenzymatic strategy for the synthesis of enantiomerically pure novel alkaloids (1S,3R)- 1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinolines is presented. The key steps are the biocatalytic stereoselective reductive amination of substituted 1-phenylpropan-2-one derivatives to yield chiral amines employing microbial x-transaminases, and the diastereoselective reduction of a Bischler– Napieralski imine intermediate by catalytic hydrogenation in the presence of palladium on charcoal, leading exclusively to the desired cis-isomer.
Fil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Schrittwieser, Joerg H.. University of Graz; Austria
Fil: Resch, Verena. University of Graz; Austria
Fil: Mutti, Francesco G.. University of Graz; Austria
Fil: Kroutil, Wolfgang. University of Graz; Austria
Materia
Chemoenzymatic
Alkaloids
Transaminases
Stereoselectivity
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:11336/2208
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/2208
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivativesOrden, Alejandro AgustinSchrittwieser, Joerg H.Resch, VerenaMutti, Francesco G.Kroutil, WolfgangChemoenzymaticAlkaloidsTransaminasesStereoselectivityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A chemoenzymatic strategy for the synthesis of enantiomerically pure novel alkaloids (1S,3R)- 1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinolines is presented. The key steps are the biocatalytic stereoselective reductive amination of substituted 1-phenylpropan-2-one derivatives to yield chiral amines employing microbial x-transaminases, and the diastereoselective reduction of a Bischler– Napieralski imine intermediate by catalytic hydrogenation in the presence of palladium on charcoal, leading exclusively to the desired cis-isomer.Fil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Schrittwieser, Joerg H.. University of Graz; AustriaFil: Resch, Verena. University of Graz; AustriaFil: Mutti, Francesco G.. University of Graz; AustriaFil: Kroutil, Wolfgang. University of Graz; AustriaPergamon-Elsevier Science Ltd2013-06-30info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/2208Orden, Alejandro Agustin; Schrittwieser, Joerg H.; Resch, Verena; Mutti, Francesco G.; Kroutil, Wolfgang; Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 24; 12; 30-6-2013; 744-7490957-4166enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0957416613002012info:eu-repo/semantics/altIdentifier/url/http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3912595/info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2013.05.003info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:21:10Zoai:ri.conicet.gov.ar:11336/2208instacron: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:34982025-09-29 10:21:11.196CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
title Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
spellingShingle Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
Orden, Alejandro Agustin
Chemoenzymatic
Alkaloids
Transaminases
Stereoselectivity
title_short Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
title_full Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
title_fullStr Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
title_full_unstemmed Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
title_sort Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
dc.creator.none.fl_str_mv Orden, Alejandro Agustin
Schrittwieser, Joerg H.
Resch, Verena
Mutti, Francesco G.
Kroutil, Wolfgang
author Orden, Alejandro Agustin
author_facet Orden, Alejandro Agustin
Schrittwieser, Joerg H.
Resch, Verena
Mutti, Francesco G.
Kroutil, Wolfgang
author_role author
author2 Schrittwieser, Joerg H.
Resch, Verena
Mutti, Francesco G.
Kroutil, Wolfgang
author2_role author
author
author
author
dc.subject.none.fl_str_mv Chemoenzymatic
Alkaloids
Transaminases
Stereoselectivity
topic Chemoenzymatic
Alkaloids
Transaminases
Stereoselectivity
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 chemoenzymatic strategy for the synthesis of enantiomerically pure novel alkaloids (1S,3R)- 1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinolines is presented. The key steps are the biocatalytic stereoselective reductive amination of substituted 1-phenylpropan-2-one derivatives to yield chiral amines employing microbial x-transaminases, and the diastereoselective reduction of a Bischler– Napieralski imine intermediate by catalytic hydrogenation in the presence of palladium on charcoal, leading exclusively to the desired cis-isomer.
Fil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Schrittwieser, Joerg H.. University of Graz; Austria
Fil: Resch, Verena. University of Graz; Austria
Fil: Mutti, Francesco G.. University of Graz; Austria
Fil: Kroutil, Wolfgang. University of Graz; Austria
description A chemoenzymatic strategy for the synthesis of enantiomerically pure novel alkaloids (1S,3R)- 1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinolines is presented. The key steps are the biocatalytic stereoselective reductive amination of substituted 1-phenylpropan-2-one derivatives to yield chiral amines employing microbial x-transaminases, and the diastereoselective reduction of a Bischler– Napieralski imine intermediate by catalytic hydrogenation in the presence of palladium on charcoal, leading exclusively to the desired cis-isomer.
publishDate 2013
dc.date.none.fl_str_mv 2013-06-30
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/11336/2208
Orden, Alejandro Agustin; Schrittwieser, Joerg H.; Resch, Verena; Mutti, Francesco G.; Kroutil, Wolfgang; Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 24; 12; 30-6-2013; 744-749
0957-4166
url http://hdl.handle.net/11336/2208
identifier_str_mv Orden, Alejandro Agustin; Schrittwieser, Joerg H.; Resch, Verena; Mutti, Francesco G.; Kroutil, Wolfgang; Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 24; 12; 30-6-2013; 744-749
0957-4166
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0957416613002012
info:eu-repo/semantics/altIdentifier/url/http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3912595/
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2013.05.003
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 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
_version_ 1844614199521574912
score 13.070432

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