Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone
A series of fatty acid derivatives of hydrocortisone has been prepared by an enzymatic methodology. Nine 21-monoacyl products and one 3,11,17-triacetyl derivative, nine of them novel compounds, were obtained in a highly regioselective way through lipase-catalyzed esterification, transesterification...
| Published in: | Steroids |
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| Main Authors: | , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Elsevier Science Inc
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| Subjects: | |
| Online Access: | http://hdl.handle.net/11336/70793 |
| _version_ | 1821731258071252992 |
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| author | Quintana, Paula Gabriela Baldessari, Alicia |
| author_facet | Quintana, Paula Gabriela Baldessari, Alicia |
| author_sort | Quintana, Paula Gabriela |
| collection | CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) |
| container_issue | 13-14 |
| container_start_page | 1007 |
| container_title | Steroids |
| container_volume | 74 |
| description | A series of fatty acid derivatives of hydrocortisone has been prepared by an enzymatic methodology. Nine 21-monoacyl products and one 3,11,17-triacetyl derivative, nine of them novel compounds, were obtained in a highly regioselective way through lipase-catalyzed esterification, transesterification and alcoholysis reactions. The influence of various reaction parameters such as acylating agent: substrate ratio, enzyme: substrate ratio, solvent, temperature and nature of acylating agent and alcohol was evaluated. Among the tested lipases, Candida antarctica lipase appeared to be the most appropriate and showed a high efficient behavior especially in a one-pot transesterification. The advantages presented by this methodology, such as mild reaction conditions and low environmental impact, make the biocatalysis a convenient way to prepare acyl derivatives of hydrocortisone. These lipophilic compounds are potential products in the pharmaceutical industry. Fil: Quintana, Paula Gabriela. 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 |
| format | Article in Journal/Newspaper |
| genre | Antarc* Antarctica |
| genre_facet | Antarc* Antarctica |
| geographic | Argentina Alicia |
| geographic_facet | Argentina Alicia |
| id | ftconicet:oai:ri.conicet.gov.ar:11336/70793 |
| institution | Open Polar |
| language | English |
| long_lat | ENVELOPE(-63.483,-63.483,-64.833,-64.833) |
| op_collection_id | ftconicet |
| op_container_end_page | 1014 |
| op_doi | https://doi.org/10.1016/j.steroids.2009.07.010 |
| op_relation | info:eu-repo/semantics/altIdentifier/doi/10.1016/j.steroids.2009.07.010 info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0039128X09001792 http://hdl.handle.net/11336/70793 Quintana, Paula Gabriela; Baldessari, Alicia; Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone; Elsevier Science Inc; Steroids; 74; 13-14; 11-2009; 1007-1014 0039-128X CONICET Digital CONICET |
| op_rights | info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-nd/2.5/ar/ |
| publisher | Elsevier Science Inc |
| record_format | openpolar |
| spelling | ftconicet:oai:ri.conicet.gov.ar:11336/70793 2025-01-16T19:17:58+00:00 Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone Quintana, Paula Gabriela Baldessari, Alicia application/pdf http://hdl.handle.net/11336/70793 eng eng Elsevier Science Inc info:eu-repo/semantics/altIdentifier/doi/10.1016/j.steroids.2009.07.010 info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0039128X09001792 http://hdl.handle.net/11336/70793 Quintana, Paula Gabriela; Baldessari, Alicia; Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone; Elsevier Science Inc; Steroids; 74; 13-14; 11-2009; 1007-1014 0039-128X CONICET Digital CONICET info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-nd/2.5/ar/ Hydrocortisone Fatty Acid Esters Lipase-Catalyzed Reactions 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.steroids.2009.07.010 2023-09-24T19:38:42Z A series of fatty acid derivatives of hydrocortisone has been prepared by an enzymatic methodology. Nine 21-monoacyl products and one 3,11,17-triacetyl derivative, nine of them novel compounds, were obtained in a highly regioselective way through lipase-catalyzed esterification, transesterification and alcoholysis reactions. The influence of various reaction parameters such as acylating agent: substrate ratio, enzyme: substrate ratio, solvent, temperature and nature of acylating agent and alcohol was evaluated. Among the tested lipases, Candida antarctica lipase appeared to be the most appropriate and showed a high efficient behavior especially in a one-pot transesterification. The advantages presented by this methodology, such as mild reaction conditions and low environmental impact, make the biocatalysis a convenient way to prepare acyl derivatives of hydrocortisone. These lipophilic compounds are potential products in the pharmaceutical industry. Fil: Quintana, Paula Gabriela. 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 Article in Journal/Newspaper Antarc* Antarctica CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) Argentina Alicia ENVELOPE(-63.483,-63.483,-64.833,-64.833) Steroids 74 13-14 1007 1014 |
| spellingShingle | Hydrocortisone Fatty Acid Esters Lipase-Catalyzed Reactions https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 Quintana, Paula Gabriela Baldessari, Alicia Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
| title | Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
| title_full | Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
| title_fullStr | Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
| title_full_unstemmed | Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
| title_short | Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
| title_sort | lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone |
| topic | Hydrocortisone Fatty Acid Esters Lipase-Catalyzed Reactions https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| topic_facet | Hydrocortisone Fatty Acid Esters Lipase-Catalyzed Reactions https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| url | http://hdl.handle.net/11336/70793 |