Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution

A series of acetoxy derivatives of androstane and pregnane was deacetylated in organic solvents by microbial lipases. The best results were obtained with lipase from Candida antarctica (CAL B), Candida rugosa (CRL) and Pseudomonas sp. (PSL). In some derivatives, CAL B and CRL showed a regioselective...

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Published in:Journal of Molecular Catalysis B: Enzymatic
Main Authors: Bruttomesso, Andrea, Baldessari, Alicia
Format: Article in Journal/Newspaper
Language:English
Published: Elsevier Science
Subjects:
ANDROSTANE
LIPASE-CATALYSED DEACETYLATION
PREGNANE
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Argentina
Rugosa
Alicia
Antarc*
Antarctica
Online Access:http://hdl.handle.net/11336/84865
id ftconicet:oai:ri.conicet.gov.ar:11336/84865
record_format openpolar
spelling ftconicet:oai:ri.conicet.gov.ar:11336/84865 2023-10-09T21:45:53+02:00 Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution Bruttomesso, Andrea Baldessari, Alicia application/pdf http://hdl.handle.net/11336/84865 eng eng Elsevier Science info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117704000499 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2003.10.011 http://hdl.handle.net/11336/84865 Bruttomesso, Andrea; Baldessari, Alicia; Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 29; 1-6; 6-2004; 149-153 1381-1177 CONICET Digital CONICET info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ ANDROSTANE LIPASE-CATALYSED DEACETYLATION PREGNANE https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion ftconicet https://doi.org/10.1016/j.molcatb.2003.10.011 2023-09-24T18:48:37Z A series of acetoxy derivatives of androstane and pregnane was deacetylated in organic solvents by microbial lipases. The best results were obtained with lipase from Candida antarctica (CAL B), Candida rugosa (CRL) and Pseudomonas sp. (PSL). In some derivatives, CAL B and CRL showed a regioselective behaviour towards the removal of the 3β- or 16α/16β-acetyl group. The results of the enzymatic deacetylation of pregnanes and androstanes substituted by various groups containing an sp2-hybridised C-atom in ring D could suggest that CAL B activity seems to be conditioned by the occurrence of a polar carbon double bond in this part of the steroid skeleton. Ten new steroid derivatives were obtained through this approach. Fil: Bruttomesso, Andrea. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina Article in Journal/Newspaper Antarc* Antarctica CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) Argentina Rugosa ENVELOPE(-61.250,-61.250,-62.633,-62.633) Alicia ENVELOPE(-63.483,-63.483,-64.833,-64.833) Journal of Molecular Catalysis B: Enzymatic 29 1-6 149 153
institution Open Polar
collection CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas)
op_collection_id ftconicet
language English
topic ANDROSTANE
LIPASE-CATALYSED DEACETYLATION
PREGNANE
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
spellingShingle ANDROSTANE
LIPASE-CATALYSED DEACETYLATION
PREGNANE
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Bruttomesso, Andrea
Baldessari, Alicia
Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution
topic_facet ANDROSTANE
LIPASE-CATALYSED DEACETYLATION
PREGNANE
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description A series of acetoxy derivatives of androstane and pregnane was deacetylated in organic solvents by microbial lipases. The best results were obtained with lipase from Candida antarctica (CAL B), Candida rugosa (CRL) and Pseudomonas sp. (PSL). In some derivatives, CAL B and CRL showed a regioselective behaviour towards the removal of the 3β- or 16α/16β-acetyl group. The results of the enzymatic deacetylation of pregnanes and androstanes substituted by various groups containing an sp2-hybridised C-atom in ring D could suggest that CAL B activity seems to be conditioned by the occurrence of a polar carbon double bond in this part of the steroid skeleton. Ten new steroid derivatives were obtained through this approach. Fil: Bruttomesso, Andrea. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
format Article in Journal/Newspaper
author Bruttomesso, Andrea
Baldessari, Alicia
author_facet Bruttomesso, Andrea
Baldessari, Alicia
author_sort Bruttomesso, Andrea
title Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution
title_short Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution
title_full Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution
title_fullStr Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution
title_full_unstemmed Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution
title_sort lipase-catalysed deacetylation of androstane and pregnane derivatives: influence of ring d substitution
publisher Elsevier Science
url http://hdl.handle.net/11336/84865
long_lat ENVELOPE(-61.250,-61.250,-62.633,-62.633)
ENVELOPE(-63.483,-63.483,-64.833,-64.833)
geographic Argentina
Rugosa
Alicia
geographic_facet Argentina
Rugosa
Alicia
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_relation info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117704000499
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2003.10.011
http://hdl.handle.net/11336/84865
Bruttomesso, Andrea; Baldessari, Alicia; Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 29; 1-6; 6-2004; 149-153
1381-1177
CONICET Digital
CONICET
op_rights info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
op_doi https://doi.org/10.1016/j.molcatb.2003.10.011
container_title Journal of Molecular Catalysis B: Enzymatic
container_volume 29
container_issue 1-6
container_start_page 149
op_container_end_page 153
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