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...
| Published in: | Journal of Molecular Catalysis B: Enzymatic |
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| Main Authors: | , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Elsevier Science
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| Subjects: | |
| Online Access: | http://hdl.handle.net/11336/84865 |
| _version_ | 1821688699550695424 |
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| author | Bruttomesso, Andrea Baldessari, Alicia |
| author_facet | Bruttomesso, Andrea Baldessari, Alicia |
| author_sort | Bruttomesso, Andrea |
| collection | CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) |
| container_issue | 1-6 |
| container_start_page | 149 |
| container_title | Journal of Molecular Catalysis B: Enzymatic |
| container_volume | 29 |
| 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 |
| genre | Antarc* Antarctica |
| genre_facet | Antarc* Antarctica |
| geographic | Alicia Argentina Rugosa |
| geographic_facet | Alicia Argentina Rugosa |
| id | ftconicet:oai:ri.conicet.gov.ar:11336/84865 |
| institution | Open Polar |
| language | English |
| long_lat | ENVELOPE(-63.483,-63.483,-64.833,-64.833) ENVELOPE(-61.250,-61.250,-62.633,-62.633) |
| op_collection_id | ftconicet |
| op_container_end_page | 153 |
| op_doi | https://doi.org/10.1016/j.molcatb.2003.10.011 |
| 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/ |
| publisher | Elsevier Science |
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| spelling | ftconicet:oai:ri.conicet.gov.ar:11336/84865 2025-01-16T19:14:53+00:00 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) Alicia ENVELOPE(-63.483,-63.483,-64.833,-64.833) Argentina Rugosa ENVELOPE(-61.250,-61.250,-62.633,-62.633) Journal of Molecular Catalysis B: Enzymatic 29 1-6 149 153 |
| 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 |
| title | 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_short | 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 |
| topic | ANDROSTANE LIPASE-CATALYSED DEACETYLATION PREGNANE https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| topic_facet | ANDROSTANE LIPASE-CATALYSED DEACETYLATION PREGNANE https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| url | http://hdl.handle.net/11336/84865 |