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

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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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Autores principales:	Bruttomesso, A.C., Baldessari, A.
Formato:	JOUR
Materias:	Androstane Lipase-catalysed deacetylation Pregnane Acetylation Carbon Catalysis Derivatives Organic solvents Substitution reactions 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 Pseudomonas sp.
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_13811177_v29_n1-6_p149_Bruttomesso
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_13811177_v29_n1-6_p149_Bruttomesso
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spelling	todo:paper_13811177_v29_n1-6_p149_Bruttomesso2023-10-03T16:11:43Z Lipase-catalysed deacetylation of androstane and pregnane derivatives: Influence of ring D substitution Bruttomesso, A.C. Baldessari, A. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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, A.C. Baldessari, A. 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.
format	JOUR
author	Bruttomesso, A.C. Baldessari, A.
author_facet	Bruttomesso, A.C. Baldessari, A.
author_sort	Bruttomesso, A.C.
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
url	http://hdl.handle.net/20.500.12110/paper_13811177_v29_n1-6_p149_Bruttomesso
work_keys_str_mv	AT bruttomessoac lipasecatalyseddeacetylationofandrostaneandpregnanederivativesinfluenceofringdsubstitution AT baldessaria lipasecatalyseddeacetylationofandrostaneandpregnanederivativesinfluenceofringdsubstitution
_version_	1807316088164188160

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

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