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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/61798
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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 Técnicas2025-09-29T09:46:22Zoai: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:34982025-09-29 09:46:22.746CONICET 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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1844613448389885952 |
score |
13.070432 |