Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction

A simple and efficient route for the synthesis of new glycoconjugates has been developed. The approach acts as a model for a mini-library of compounds with a deoxy-selenosugar core joined to a polyphenolic moiety with well-known antioxidant properties. An unexpected stereocontrol detected in the Mit...

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Autores principales: Serpico, Luigia, De Nisco, Mauro, Cermola, Flavio, Manfra, Michele, Pedatella, Silvana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8123786/
https://www.ncbi.nlm.nih.gov/pubmed/33925409
http://dx.doi.org/10.3390/molecules26092541
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author Serpico, Luigia
De Nisco, Mauro
Cermola, Flavio
Manfra, Michele
Pedatella, Silvana
author_facet Serpico, Luigia
De Nisco, Mauro
Cermola, Flavio
Manfra, Michele
Pedatella, Silvana
author_sort Serpico, Luigia
collection PubMed
description A simple and efficient route for the synthesis of new glycoconjugates has been developed. The approach acts as a model for a mini-library of compounds with a deoxy-selenosugar core joined to a polyphenolic moiety with well-known antioxidant properties. An unexpected stereocontrol detected in the Mitsunobu key reaction led to the most attractive product showing a natural d-configuration. Thus, we were able to obtain the target molecules from the commercially available d-ribose via a shorter and convenient sequence of reactions.
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spelling pubmed-81237862021-05-16 Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction Serpico, Luigia De Nisco, Mauro Cermola, Flavio Manfra, Michele Pedatella, Silvana Molecules Communication A simple and efficient route for the synthesis of new glycoconjugates has been developed. The approach acts as a model for a mini-library of compounds with a deoxy-selenosugar core joined to a polyphenolic moiety with well-known antioxidant properties. An unexpected stereocontrol detected in the Mitsunobu key reaction led to the most attractive product showing a natural d-configuration. Thus, we were able to obtain the target molecules from the commercially available d-ribose via a shorter and convenient sequence of reactions. MDPI 2021-04-27 /pmc/articles/PMC8123786/ /pubmed/33925409 http://dx.doi.org/10.3390/molecules26092541 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Serpico, Luigia
De Nisco, Mauro
Cermola, Flavio
Manfra, Michele
Pedatella, Silvana
Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction
title Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction
title_full Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction
title_fullStr Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction
title_full_unstemmed Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction
title_short Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction
title_sort stereoselective synthesis of selenium-containing glycoconjugates via the mitsunobu reaction
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8123786/
https://www.ncbi.nlm.nih.gov/pubmed/33925409
http://dx.doi.org/10.3390/molecules26092541
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