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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ftunibueairesbd:todo:paper_10643745_v861_n_p457_Baldessari 2023-10-29T02:31:46+01:00 Lipases in green chemistry: Acylation and alcoholysis on steroids and nucleosides Baldessari, A. Iglesias, L.E. https://hdl.handle.net/20.500.12110/paper_10643745_v861_n_p457_Baldessari unknown http://hdl.handle.net/20.500.12110/paper_10643745_v861_n_p457_Baldessari info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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 stereoisomerism synthesis Androstanes Biological Agents Cholestanes Fatty Acids Fungal Proteins Green Chemistry Technology Lipase Pregnanes Prodrugs SER ftunibueairesbd https://doi.org/20.500.12110/paper_10643745_v861_n_p457_Baldessari 2023-10-05T01:59:02Z 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. Other/Unknown Material Antarc* Antarctica Biblioteca Digital FCEN-UBA (Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires) |
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Biblioteca Digital FCEN-UBA (Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires) |
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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 stereoisomerism synthesis Androstanes Biological Agents Cholestanes Fatty Acids Fungal Proteins Green Chemistry Technology Lipase Pregnanes Prodrugs |
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 stereoisomerism synthesis Androstanes Biological Agents Cholestanes Fatty Acids Fungal Proteins Green Chemistry Technology Lipase Pregnanes Prodrugs 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 stereoisomerism synthesis Androstanes Biological Agents Cholestanes Fatty Acids Fungal Proteins Green Chemistry Technology Lipase Pregnanes Prodrugs |
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 |
Other/Unknown Material |
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 |
https://hdl.handle.net/20.500.12110/paper_10643745_v861_n_p457_Baldessari |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
http://hdl.handle.net/20.500.12110/paper_10643745_v861_n_p457_Baldessari |
op_rights |
info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar |
op_doi |
https://doi.org/20.500.12110/paper_10643745_v861_n_p457_Baldessari |
_version_ |
1781052547939696640 |