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...
Guardado en:
| Autores principales: | , |
|---|---|
| Publicado: |
2004
|
| Materias: | |
| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v29_n1-6_p149_Bruttomesso http://hdl.handle.net/20.500.12110/paper_13811177_v29_n1-6_p149_Bruttomesso |
| Aporte de: |
| id |
paper:paper_13811177_v29_n1-6_p149_Bruttomesso |
|---|---|
| record_format |
dspace |
| spelling |
paper:paper_13811177_v29_n1-6_p149_Bruttomesso2025-07-30T18:48:06Z Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution Bruttomesso, Andrea Claudia Baldessari, Alicia Androstane Lipase-catalysed deacetylation Pregnane Acetylation Carbon Catalysis Derivatives Organic solvents Substitution reactions Androstane Pregnane Enzymes acetic acid derivative bacterial enzyme carbon organic solvent prasterone pregnane derivative steroid triacylglycerol lipase atom Candida antarctica Candida rugosa catalysis chemical bond conference paper deacetylation hybridization microorganism Pseudomonas stereochemistry Candida Candida antarctica Candida rugosa Pseudomonas Pseudomonas sp. 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. © 2004 Elsevier B.V. All rights reserved. Fil:Bruttomesso, A.C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Baldessari, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2004 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v29_n1-6_p149_Bruttomesso http://hdl.handle.net/20.500.12110/paper_13811177_v29_n1-6_p149_Bruttomesso |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Androstane Lipase-catalysed deacetylation Pregnane Acetylation Carbon Catalysis Derivatives Organic solvents Substitution reactions Androstane Pregnane Enzymes acetic acid derivative bacterial enzyme carbon organic solvent prasterone pregnane derivative steroid triacylglycerol lipase atom Candida antarctica Candida rugosa catalysis chemical bond conference paper deacetylation hybridization microorganism Pseudomonas stereochemistry Candida Candida antarctica Candida rugosa Pseudomonas Pseudomonas sp. |
| spellingShingle |
Androstane Lipase-catalysed deacetylation Pregnane Acetylation Carbon Catalysis Derivatives Organic solvents Substitution reactions Androstane Pregnane Enzymes acetic acid derivative bacterial enzyme carbon organic solvent prasterone pregnane derivative steroid triacylglycerol lipase atom Candida antarctica Candida rugosa catalysis chemical bond conference paper deacetylation hybridization microorganism Pseudomonas stereochemistry Candida Candida antarctica Candida rugosa Pseudomonas Pseudomonas sp. Bruttomesso, Andrea Claudia Baldessari, Alicia Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution |
| topic_facet |
Androstane Lipase-catalysed deacetylation Pregnane Acetylation Carbon Catalysis Derivatives Organic solvents Substitution reactions Androstane Pregnane Enzymes acetic acid derivative bacterial enzyme carbon organic solvent prasterone pregnane derivative steroid triacylglycerol lipase atom Candida antarctica Candida rugosa catalysis chemical bond conference paper deacetylation hybridization microorganism Pseudomonas stereochemistry Candida Candida antarctica Candida rugosa Pseudomonas Pseudomonas sp. |
| 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. © 2004 Elsevier B.V. All rights reserved. |
| author |
Bruttomesso, Andrea Claudia Baldessari, Alicia |
| author_facet |
Bruttomesso, Andrea Claudia Baldessari, Alicia |
| author_sort |
Bruttomesso, Andrea Claudia |
| 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 |
| publishDate |
2004 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v29_n1-6_p149_Bruttomesso http://hdl.handle.net/20.500.12110/paper_13811177_v29_n1-6_p149_Bruttomesso |
| work_keys_str_mv |
AT bruttomessoandreaclaudia lipasecatalyseddeacetylationofandrostaneandpregnanederivativesinfluenceofringdsubstitution AT baldessarialicia lipasecatalyseddeacetylationofandrostaneandpregnanederivativesinfluenceofringdsubstitution |
| _version_ |
1840328078317846528 |