Aspergillus genus as a source of new catalysts for sulfide oxidation

Autores
Mascotti, María Laura; Orden, Alejandro Agustin; Bisogno, Fabricio Román; De Gonzalo, Gonzalo; Kurina Sanz, Marcela Beatriz
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
This work extends the present knowledge about the ability of filamentous fungi to selectively transform sulfur-containing compounds. Here, it has been demonstrated that several species of the Aspergillus genus are able to perform chemo- and stereoselective oxidation of organic sulfides. Two substrates were chosen as models, the aliphatic cyclohexyl(methyl)sulfide and the alkyl aryl sulfide, thioanisole. All the tested strains showed the ability to oxidize cyclohexyl(methyl)sulfide, whereas most of them oxidized thioanisole. In all cases R-stereoselectivity was observed and full chemoselectivity was verified since no sulfone was detected. Several biotransformation parameters such as the employment of growing or resting cell, different head-space volumes, age of the cultures, bio-reaction times and biocatalyst/substrate ratios resulted crucial in the optimization of the processes. Thus, when using isopropyl alcohol as co-solvent in growing cell systems, chemo- and stereoselectivity could be modulated. Among the studied strains, Aspergillus japonicus ICFC 744/11 was found to be a promising whole cell biocatalyst to prepare enantioenriched sulfoxides since after optimization, either conversion and optical purity of (R)-cyclohexyl(methyl)sulfoxide were excellent (c: 100%, ee > 99%). © 2012 Elsevier B.V.
Fil: Mascotti, María Laura. 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
Fil: Bisogno, Fabricio Román. 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. 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: De Gonzalo, Gonzalo. Universidad de Oviedo; España
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
Materia
Aspergillus
Biotransformation
Chiral Sulfoxide
Stereoselective Sulfoxidation
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:11336/61798
Acceder
id CONICETDig_dd166f41324b4ee07082bfbad67382d6
oai_identifier_str oai:ri.conicet.gov.ar:11336/61798
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Aspergillus genus as a source of new catalysts for sulfide oxidationMascotti, María LauraOrden, Alejandro AgustinBisogno, Fabricio RománDe Gonzalo, GonzaloKurina Sanz, Marcela BeatrizAspergillusBiotransformationChiral SulfoxideStereoselective Sulfoxidationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/2.9https://purl.org/becyt/ford/2This work extends the present knowledge about the ability of filamentous fungi to selectively transform sulfur-containing compounds. Here, it has been demonstrated that several species of the Aspergillus genus are able to perform chemo- and stereoselective oxidation of organic sulfides. Two substrates were chosen as models, the aliphatic cyclohexyl(methyl)sulfide and the alkyl aryl sulfide, thioanisole. All the tested strains showed the ability to oxidize cyclohexyl(methyl)sulfide, whereas most of them oxidized thioanisole. In all cases R-stereoselectivity was observed and full chemoselectivity was verified since no sulfone was detected. Several biotransformation parameters such as the employment of growing or resting cell, different head-space volumes, age of the cultures, bio-reaction times and biocatalyst/substrate ratios resulted crucial in the optimization of the processes. Thus, when using isopropyl alcohol as co-solvent in growing cell systems, chemo- and stereoselectivity could be modulated. Among the studied strains, Aspergillus japonicus ICFC 744/11 was found to be a promising whole cell biocatalyst to prepare enantioenriched sulfoxides since after optimization, either conversion and optical purity of (R)-cyclohexyl(methyl)sulfoxide were excellent (c: 100%, ee > 99%). © 2012 Elsevier B.V.Fil: Mascotti, María Laura. 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; ArgentinaFil: Bisogno, Fabricio Román. 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. 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: De Gonzalo, Gonzalo. Universidad de Oviedo; EspañaFil: 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; ArgentinaElsevier Science2012-10info: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/11336/61798Mascotti, María Laura; Orden, Alejandro Agustin; Bisogno, Fabricio Román; De Gonzalo, Gonzalo; Kurina Sanz, Marcela Beatriz; Aspergillus genus as a source of new catalysts for sulfide oxidation; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 82; 10-2012; 32-361381-1177CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2012.05.003info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117712001257info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:15:12Zoai:ri.conicet.gov.ar:11336/61798instacron: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:34982025-10-22 11:15:12.387CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Aspergillus genus as a source of new catalysts for sulfide oxidation
title Aspergillus genus as a source of new catalysts for sulfide oxidation
spellingShingle Aspergillus genus as a source of new catalysts for sulfide oxidation
Mascotti, María Laura
Aspergillus
Biotransformation
Chiral Sulfoxide
Stereoselective Sulfoxidation
title_short Aspergillus genus as a source of new catalysts for sulfide oxidation
title_full Aspergillus genus as a source of new catalysts for sulfide oxidation
title_fullStr Aspergillus genus as a source of new catalysts for sulfide oxidation
title_full_unstemmed Aspergillus genus as a source of new catalysts for sulfide oxidation
title_sort Aspergillus genus as a source of new catalysts for sulfide oxidation
dc.creator.none.fl_str_mv Mascotti, María Laura
Orden, Alejandro Agustin
Bisogno, Fabricio Román
De Gonzalo, Gonzalo
Kurina Sanz, Marcela Beatriz
author Mascotti, María Laura
author_facet Mascotti, María Laura
Orden, Alejandro Agustin
Bisogno, Fabricio Román
De Gonzalo, Gonzalo
Kurina Sanz, Marcela Beatriz
author_role author
author2 Orden, Alejandro Agustin
Bisogno, Fabricio Román
De Gonzalo, Gonzalo
Kurina Sanz, Marcela Beatriz
author2_role author
author
author
author
dc.subject.none.fl_str_mv Aspergillus
Biotransformation
Chiral Sulfoxide
Stereoselective Sulfoxidation
topic Aspergillus
Biotransformation
Chiral Sulfoxide
Stereoselective Sulfoxidation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv This work extends the present knowledge about the ability of filamentous fungi to selectively transform sulfur-containing compounds. Here, it has been demonstrated that several species of the Aspergillus genus are able to perform chemo- and stereoselective oxidation of organic sulfides. Two substrates were chosen as models, the aliphatic cyclohexyl(methyl)sulfide and the alkyl aryl sulfide, thioanisole. All the tested strains showed the ability to oxidize cyclohexyl(methyl)sulfide, whereas most of them oxidized thioanisole. In all cases R-stereoselectivity was observed and full chemoselectivity was verified since no sulfone was detected. Several biotransformation parameters such as the employment of growing or resting cell, different head-space volumes, age of the cultures, bio-reaction times and biocatalyst/substrate ratios resulted crucial in the optimization of the processes. Thus, when using isopropyl alcohol as co-solvent in growing cell systems, chemo- and stereoselectivity could be modulated. Among the studied strains, Aspergillus japonicus ICFC 744/11 was found to be a promising whole cell biocatalyst to prepare enantioenriched sulfoxides since after optimization, either conversion and optical purity of (R)-cyclohexyl(methyl)sulfoxide were excellent (c: 100%, ee > 99%). © 2012 Elsevier B.V.
Fil: Mascotti, María Laura. 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
Fil: Bisogno, Fabricio Román. 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. 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: De Gonzalo, Gonzalo. Universidad de Oviedo; España
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
description This work extends the present knowledge about the ability of filamentous fungi to selectively transform sulfur-containing compounds. Here, it has been demonstrated that several species of the Aspergillus genus are able to perform chemo- and stereoselective oxidation of organic sulfides. Two substrates were chosen as models, the aliphatic cyclohexyl(methyl)sulfide and the alkyl aryl sulfide, thioanisole. All the tested strains showed the ability to oxidize cyclohexyl(methyl)sulfide, whereas most of them oxidized thioanisole. In all cases R-stereoselectivity was observed and full chemoselectivity was verified since no sulfone was detected. Several biotransformation parameters such as the employment of growing or resting cell, different head-space volumes, age of the cultures, bio-reaction times and biocatalyst/substrate ratios resulted crucial in the optimization of the processes. Thus, when using isopropyl alcohol as co-solvent in growing cell systems, chemo- and stereoselectivity could be modulated. Among the studied strains, Aspergillus japonicus ICFC 744/11 was found to be a promising whole cell biocatalyst to prepare enantioenriched sulfoxides since after optimization, either conversion and optical purity of (R)-cyclohexyl(methyl)sulfoxide were excellent (c: 100%, ee > 99%). © 2012 Elsevier B.V.
publishDate 2012
dc.date.none.fl_str_mv 2012-10
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/11336/61798
Mascotti, María Laura; Orden, Alejandro Agustin; Bisogno, Fabricio Román; De Gonzalo, Gonzalo; Kurina Sanz, Marcela Beatriz; Aspergillus genus as a source of new catalysts for sulfide oxidation; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 82; 10-2012; 32-36
1381-1177
CONICET Digital
CONICET
url http://hdl.handle.net/11336/61798
identifier_str_mv Mascotti, María Laura; Orden, Alejandro Agustin; Bisogno, Fabricio Román; De Gonzalo, Gonzalo; Kurina Sanz, Marcela Beatriz; Aspergillus genus as a source of new catalysts for sulfide oxidation; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 82; 10-2012; 32-36
1381-1177
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.molcatb.2012.05.003
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117712001257
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 Science
publisher.none.fl_str_mv Elsevier Science
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 12.982451

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