Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids

Detalhes bibliográficos
Autor(a) principal: Silva, M. Manuel Cruz
Data de Publicação: 2004
Outros Autores: Riva, Sergio, Melo, M. Luísa Sá e
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10316/5767
https://doi.org/10.1016/j.tetasy.2004.02.010
Resumo: Stereoisomerically pure 3[beta]-hydroxy-5,6-epoxysteroids were obtained by combining selective chemical methods for [alpha]- and [beta]-epoxidation of [Delta]5-unsaturated steroids with enzymatic stereoselective esterification of the 3[beta]-hydroxyl group. 5[beta],6[beta]-Epoxy-3[beta]-hydroxysteroids were efficiently acylated by Novozym 435 and lipase AK, whereas 5[alpha],6[alpha]-epoxy-3[beta]-hydroxysteroids were good substrates for Candida rugosa lipase. Mild enzymatic deacylation of the 3[beta]-acetoxy group in the presence of the epoxy functionality was also accomplished by C. rugosa lipase-mediated hydrolysis.
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spelling Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroidsStereoisomerically pure 3[beta]-hydroxy-5,6-epoxysteroids were obtained by combining selective chemical methods for [alpha]- and [beta]-epoxidation of [Delta]5-unsaturated steroids with enzymatic stereoselective esterification of the 3[beta]-hydroxyl group. 5[beta],6[beta]-Epoxy-3[beta]-hydroxysteroids were efficiently acylated by Novozym 435 and lipase AK, whereas 5[alpha],6[alpha]-epoxy-3[beta]-hydroxysteroids were good substrates for Candida rugosa lipase. Mild enzymatic deacylation of the 3[beta]-acetoxy group in the presence of the epoxy functionality was also accomplished by C. rugosa lipase-mediated hydrolysis.http://www.sciencedirect.com/science/article/B6THT-4BY3V2F-3/1/14f2ed3d64a39572337a2fd7eda277122004info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleaplication/PDFhttp://hdl.handle.net/10316/5767http://hdl.handle.net/10316/5767https://doi.org/10.1016/j.tetasy.2004.02.010engTetrahedron: Asymmetry. 15:7 (2004) 1173-1179Silva, M. Manuel CruzRiva, SergioMelo, M. Luísa Sá einfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2022-05-25T01:30:54Zoai:estudogeral.uc.pt:10316/5767Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:47:23.691767Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids
title Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids
spellingShingle Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids
Silva, M. Manuel Cruz
title_short Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids
title_full Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids
title_fullStr Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids
title_full_unstemmed Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids
title_sort Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids
author Silva, M. Manuel Cruz
author_facet Silva, M. Manuel Cruz
Riva, Sergio
Melo, M. Luísa Sá e
author_role author
author2 Riva, Sergio
Melo, M. Luísa Sá e
author2_role author
author
dc.contributor.author.fl_str_mv Silva, M. Manuel Cruz
Riva, Sergio
Melo, M. Luísa Sá e
description Stereoisomerically pure 3[beta]-hydroxy-5,6-epoxysteroids were obtained by combining selective chemical methods for [alpha]- and [beta]-epoxidation of [Delta]5-unsaturated steroids with enzymatic stereoselective esterification of the 3[beta]-hydroxyl group. 5[beta],6[beta]-Epoxy-3[beta]-hydroxysteroids were efficiently acylated by Novozym 435 and lipase AK, whereas 5[alpha],6[alpha]-epoxy-3[beta]-hydroxysteroids were good substrates for Candida rugosa lipase. Mild enzymatic deacylation of the 3[beta]-acetoxy group in the presence of the epoxy functionality was also accomplished by C. rugosa lipase-mediated hydrolysis.
publishDate 2004
dc.date.none.fl_str_mv 2004
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dc.type.driver.fl_str_mv info:eu-repo/semantics/article
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status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10316/5767
http://hdl.handle.net/10316/5767
https://doi.org/10.1016/j.tetasy.2004.02.010
url http://hdl.handle.net/10316/5767
https://doi.org/10.1016/j.tetasy.2004.02.010
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Tetrahedron: Asymmetry. 15:7 (2004) 1173-1179
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv aplication/PDF
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