Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa

Autores
Aguirre Pranzoni, Celeste Beatriz; Tosso, Rodrigo David; Bisogno, Fabricio Román; Kurina Sanz, Marcela Beatriz; Orden, Alejandro Agustin
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Chemoenzymatic strategies for the preparation of enantiopure β-hydroxytriazoles were designed. These and other related compounds are particularly relevant because of their antitubercular bioactivities and as β-adrenergic receptor blockers. The ability of Rhodotorula mucilaginosa LSL to stereoselectively reduce prochiral ketones coupled to copper(I)-catalyzed azide-alkyne cycloaddition was exploited. The reactions were performed in aqueous medium and at room temperature. R. mucilaginosa LSL offered the advantage of internal redox cofactor recycling. Notably, the biocatalyst was compatible with all the chemicals required namely sodium azide, copper sulfate and alkynes and showed a broad substrate scope reducing small-bulky and bulky-bulky ketones stereoselectively. Considering this, two one-pot processes were assessed to synthesize enantiopure (R)-β-hydroxytriazoles. A one-pot, three-step sequential transformation allowed obtaining enantiopure products up to 65% yield starting from α-chloro arylketones. On the other hand, with α-bromo arylketones, a one-pot cascade process furnished the same products in ca 80% isolated yield.
Fil: Aguirre Pranzoni, Celeste Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Física Aplicada "Dr. Jorge Andrés Zgrablich". Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto de Física Aplicada "Dr. Jorge Andrés Zgrablich"; Argentina
Fil: Tosso, Rodrigo David. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Bisogno, Fabricio Román. 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: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Materia
(R)-Β-HYDROXYTRIAZOLES
BIOCATALYSIS
BIOREDUCTION
BULKY-BULKY KETONES
DIVERGENT-CONVERGENT PROCESS
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:11336/124995
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/124995
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosaAguirre Pranzoni, Celeste BeatrizTosso, Rodrigo DavidBisogno, Fabricio RománKurina Sanz, Marcela BeatrizOrden, Alejandro Agustin(R)-Β-HYDROXYTRIAZOLESBIOCATALYSISBIOREDUCTIONBULKY-BULKY KETONESDIVERGENT-CONVERGENT PROCESSSTEREOSELECTIVITYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Chemoenzymatic strategies for the preparation of enantiopure β-hydroxytriazoles were designed. These and other related compounds are particularly relevant because of their antitubercular bioactivities and as β-adrenergic receptor blockers. The ability of Rhodotorula mucilaginosa LSL to stereoselectively reduce prochiral ketones coupled to copper(I)-catalyzed azide-alkyne cycloaddition was exploited. The reactions were performed in aqueous medium and at room temperature. R. mucilaginosa LSL offered the advantage of internal redox cofactor recycling. Notably, the biocatalyst was compatible with all the chemicals required namely sodium azide, copper sulfate and alkynes and showed a broad substrate scope reducing small-bulky and bulky-bulky ketones stereoselectively. Considering this, two one-pot processes were assessed to synthesize enantiopure (R)-β-hydroxytriazoles. A one-pot, three-step sequential transformation allowed obtaining enantiopure products up to 65% yield starting from α-chloro arylketones. On the other hand, with α-bromo arylketones, a one-pot cascade process furnished the same products in ca 80% isolated yield.Fil: Aguirre Pranzoni, Celeste Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Física Aplicada "Dr. Jorge Andrés Zgrablich". Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto de Física Aplicada "Dr. Jorge Andrés Zgrablich"; ArgentinaFil: Tosso, Rodrigo David. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Bisogno, Fabricio Román. 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: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaElsevier2019-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/124995Aguirre Pranzoni, Celeste Beatriz; Tosso, Rodrigo David; Bisogno, Fabricio Román; Kurina Sanz, Marcela Beatriz; Orden, Alejandro Agustin; Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa; Elsevier; Process Biochemistry; 79; 4-2019; 114-1171359-5113CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.procbio.2018.12.011info:eu-repo/semantics/altIdentifier/url/www.sciencedirect.com/science/article/abs/pii/S1359511318313953info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:00:40Zoai:ri.conicet.gov.ar:11336/124995instacron: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:34982025-09-10 13:00:41.012CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa
title Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa
spellingShingle Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa
Aguirre Pranzoni, Celeste Beatriz
(R)-Β-HYDROXYTRIAZOLES
BIOCATALYSIS
BIOREDUCTION
BULKY-BULKY KETONES
DIVERGENT-CONVERGENT PROCESS
STEREOSELECTIVITY
title_short Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa
title_full Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa
title_fullStr Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa
title_full_unstemmed Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa
title_sort Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa
dc.creator.none.fl_str_mv Aguirre Pranzoni, Celeste Beatriz
Tosso, Rodrigo David
Bisogno, Fabricio Román
Kurina Sanz, Marcela Beatriz
Orden, Alejandro Agustin
author Aguirre Pranzoni, Celeste Beatriz
author_facet Aguirre Pranzoni, Celeste Beatriz
Tosso, Rodrigo David
Bisogno, Fabricio Román
Kurina Sanz, Marcela Beatriz
Orden, Alejandro Agustin
author_role author
author2 Tosso, Rodrigo David
Bisogno, Fabricio Román
Kurina Sanz, Marcela Beatriz
Orden, Alejandro Agustin
author2_role author
author
author
author
dc.subject.none.fl_str_mv (R)-Β-HYDROXYTRIAZOLES
BIOCATALYSIS
BIOREDUCTION
BULKY-BULKY KETONES
DIVERGENT-CONVERGENT PROCESS
STEREOSELECTIVITY
topic (R)-Β-HYDROXYTRIAZOLES
BIOCATALYSIS
BIOREDUCTION
BULKY-BULKY KETONES
DIVERGENT-CONVERGENT PROCESS
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 Chemoenzymatic strategies for the preparation of enantiopure β-hydroxytriazoles were designed. These and other related compounds are particularly relevant because of their antitubercular bioactivities and as β-adrenergic receptor blockers. The ability of Rhodotorula mucilaginosa LSL to stereoselectively reduce prochiral ketones coupled to copper(I)-catalyzed azide-alkyne cycloaddition was exploited. The reactions were performed in aqueous medium and at room temperature. R. mucilaginosa LSL offered the advantage of internal redox cofactor recycling. Notably, the biocatalyst was compatible with all the chemicals required namely sodium azide, copper sulfate and alkynes and showed a broad substrate scope reducing small-bulky and bulky-bulky ketones stereoselectively. Considering this, two one-pot processes were assessed to synthesize enantiopure (R)-β-hydroxytriazoles. A one-pot, three-step sequential transformation allowed obtaining enantiopure products up to 65% yield starting from α-chloro arylketones. On the other hand, with α-bromo arylketones, a one-pot cascade process furnished the same products in ca 80% isolated yield.
Fil: Aguirre Pranzoni, Celeste Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Física Aplicada "Dr. Jorge Andrés Zgrablich". Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto de Física Aplicada "Dr. Jorge Andrés Zgrablich"; Argentina
Fil: Tosso, Rodrigo David. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Bisogno, Fabricio Román. 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: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
description Chemoenzymatic strategies for the preparation of enantiopure β-hydroxytriazoles were designed. These and other related compounds are particularly relevant because of their antitubercular bioactivities and as β-adrenergic receptor blockers. The ability of Rhodotorula mucilaginosa LSL to stereoselectively reduce prochiral ketones coupled to copper(I)-catalyzed azide-alkyne cycloaddition was exploited. The reactions were performed in aqueous medium and at room temperature. R. mucilaginosa LSL offered the advantage of internal redox cofactor recycling. Notably, the biocatalyst was compatible with all the chemicals required namely sodium azide, copper sulfate and alkynes and showed a broad substrate scope reducing small-bulky and bulky-bulky ketones stereoselectively. Considering this, two one-pot processes were assessed to synthesize enantiopure (R)-β-hydroxytriazoles. A one-pot, three-step sequential transformation allowed obtaining enantiopure products up to 65% yield starting from α-chloro arylketones. On the other hand, with α-bromo arylketones, a one-pot cascade process furnished the same products in ca 80% isolated yield.
publishDate 2019
dc.date.none.fl_str_mv 2019-04
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/11336/124995
Aguirre Pranzoni, Celeste Beatriz; Tosso, Rodrigo David; Bisogno, Fabricio Román; Kurina Sanz, Marcela Beatriz; Orden, Alejandro Agustin; Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa; Elsevier; Process Biochemistry; 79; 4-2019; 114-117
1359-5113
CONICET Digital
CONICET
url http://hdl.handle.net/11336/124995
identifier_str_mv Aguirre Pranzoni, Celeste Beatriz; Tosso, Rodrigo David; Bisogno, Fabricio Román; Kurina Sanz, Marcela Beatriz; Orden, Alejandro Agustin; Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa; Elsevier; Process Biochemistry; 79; 4-2019; 114-117
1359-5113
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.procbio.2018.12.011
info:eu-repo/semantics/altIdentifier/url/www.sciencedirect.com/science/article/abs/pii/S1359511318313953
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
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
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score 12.48226

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