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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Bibliographic Details
Main Authors: Bruttomesso, Andrea Claudia, Baldessari, Alicia
Language:unknown
Published: 2004
Subjects:
Androstane
Lipase-catalysed deacetylation
Pregnane
Acetylation
Carbon
Catalysis
Derivatives
Organic solvents
Substitution reactions
Enzymes
acetic acid derivative
bacterial enzyme
organic solvent
prasterone
pregnane derivative
steroid
triacylglycerol lipase
atom
Candida antarctica
Candida rugosa
chemical bond
conference paper
deacetylation
hybridization
microorganism
Pseudomonas
stereochemistry
Candida
Pseudomonas sp
Argentina
Rugosa
Antarc*
Antarctica
Online Access:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v29_n1-6_p149_Bruttomesso
https://hdl.handle.net/20.500.12110/paper_13811177_v29_n1-6_p149_Bruttomesso
Description
Summary: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.

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