Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides

In this article, we describe the application of lipases in acylation and alcoholysis reactions on steroids and nucleosides. In the field of steroids, a variety of acetyl and fatty acid derivatives of androstanes, pregnanes, and cholestanes have been prepared through lipase-catalyzed acylation and al...

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Autores principales:	Baldessari, A., Iglesias, L.E.
Formato:	SER
Materias:	Acylation and alcoholysis reactions Green Chemistry Lipases Nucleosides Steroids androstane derivative biological product cholestane derivative fatty acid fungal protein lipase B, Candida antarctica nucleoside pregnane derivative prodrug triacylglycerol lipase acylation article biocatalysis Candida chemistry green chemistry stereoisomerism synthesis Acylation Androstanes Biocatalysis Biological Agents Cholestanes Fatty Acids Fungal Proteins Green Chemistry Technology Lipase Pregnanes Prodrugs Stereoisomerism
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_10643745_v861_n_p457_Baldessari
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_10643745_v861_n_p457_Baldessari
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spelling	todo:paper_10643745_v861_n_p457_Baldessari2023-10-03T16:01:59Z Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides Baldessari, A. Iglesias, L.E. Acylation and alcoholysis reactions Green Chemistry Lipases Nucleosides Steroids androstane derivative biological product cholestane derivative fatty acid fungal protein lipase B, Candida antarctica nucleoside pregnane derivative prodrug triacylglycerol lipase acylation article biocatalysis Candida chemistry green chemistry stereoisomerism synthesis Acylation Androstanes Biocatalysis Biological Agents Candida Cholestanes Fatty Acids Fungal Proteins Green Chemistry Technology Lipase Nucleosides Pregnanes Prodrugs Stereoisomerism In this article, we describe the application of lipases in acylation and alcoholysis reactions on steroids and nucleosides. In the field of steroids, a variety of acetyl and fatty acid derivatives of androstanes, pregnanes, and cholestanes have been prepared through lipase-catalyzed acylation and alcoholysis reactions taking advantage of the high regio- and stereoselectivity of these enzymes. The substrates as well as the products show a high degree of biological activity as neurosteroids, hormones, and glucocorticoids. The regioselective preparation of diacylated nucleosides by means of an enzymatic alcoholysis allowed the synthesis of nucleosides prodrugs or modified nucleosides. The quantitative full deacylation and dealkoxycarbonylation of nucleosides and steroids is a mild synthetic method for the deprotection of these labile compounds. Some of the reported steroid and nucleoside products are novel, and it is not possible to obtain them satisfactorily by following traditional synthetic procedures. The advantages presented by this methodology, such as selectivity, mild reaction conditions, and low environmental impact, make the lipases an important tool in the application of the principles of Green Chemistry, offering a convenient way to prepare derivatives of natural compounds with a great potential in the pharmaceutical industry. © 2012 Springer Science+Business Media New York. SER info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_10643745_v861_n_p457_Baldessari
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Acylation and alcoholysis reactions Green Chemistry Lipases Nucleosides Steroids androstane derivative biological product cholestane derivative fatty acid fungal protein lipase B, Candida antarctica nucleoside pregnane derivative prodrug triacylglycerol lipase acylation article biocatalysis Candida chemistry green chemistry stereoisomerism synthesis Acylation Androstanes Biocatalysis Biological Agents Candida Cholestanes Fatty Acids Fungal Proteins Green Chemistry Technology Lipase Nucleosides Pregnanes Prodrugs Stereoisomerism
spellingShingle	Acylation and alcoholysis reactions Green Chemistry Lipases Nucleosides Steroids androstane derivative biological product cholestane derivative fatty acid fungal protein lipase B, Candida antarctica nucleoside pregnane derivative prodrug triacylglycerol lipase acylation article biocatalysis Candida chemistry green chemistry stereoisomerism synthesis Acylation Androstanes Biocatalysis Biological Agents Candida Cholestanes Fatty Acids Fungal Proteins Green Chemistry Technology Lipase Nucleosides Pregnanes Prodrugs Stereoisomerism Baldessari, A. Iglesias, L.E. Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides
topic_facet	Acylation and alcoholysis reactions Green Chemistry Lipases Nucleosides Steroids androstane derivative biological product cholestane derivative fatty acid fungal protein lipase B, Candida antarctica nucleoside pregnane derivative prodrug triacylglycerol lipase acylation article biocatalysis Candida chemistry green chemistry stereoisomerism synthesis Acylation Androstanes Biocatalysis Biological Agents Candida Cholestanes Fatty Acids Fungal Proteins Green Chemistry Technology Lipase Nucleosides Pregnanes Prodrugs Stereoisomerism
description	In this article, we describe the application of lipases in acylation and alcoholysis reactions on steroids and nucleosides. In the field of steroids, a variety of acetyl and fatty acid derivatives of androstanes, pregnanes, and cholestanes have been prepared through lipase-catalyzed acylation and alcoholysis reactions taking advantage of the high regio- and stereoselectivity of these enzymes. The substrates as well as the products show a high degree of biological activity as neurosteroids, hormones, and glucocorticoids. The regioselective preparation of diacylated nucleosides by means of an enzymatic alcoholysis allowed the synthesis of nucleosides prodrugs or modified nucleosides. The quantitative full deacylation and dealkoxycarbonylation of nucleosides and steroids is a mild synthetic method for the deprotection of these labile compounds. Some of the reported steroid and nucleoside products are novel, and it is not possible to obtain them satisfactorily by following traditional synthetic procedures. The advantages presented by this methodology, such as selectivity, mild reaction conditions, and low environmental impact, make the lipases an important tool in the application of the principles of Green Chemistry, offering a convenient way to prepare derivatives of natural compounds with a great potential in the pharmaceutical industry. © 2012 Springer Science+Business Media New York.
format	SER
author	Baldessari, A. Iglesias, L.E.
author_facet	Baldessari, A. Iglesias, L.E.
author_sort	Baldessari, A.
title	Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides
title_short	Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides
title_full	Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides
title_fullStr	Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides
title_full_unstemmed	Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides
title_sort	lipases in green chemistry: acylation and alcoholysis on steroids and nucleosides
url	http://hdl.handle.net/20.500.12110/paper_10643745_v861_n_p457_Baldessari
work_keys_str_mv	AT baldessaria lipasesingreenchemistryacylationandalcoholysisonsteroidsandnucleosides AT iglesiasle lipasesingreenchemistryacylationandalcoholysisonsteroidsandnucleosides
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Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides

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