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Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4

A straightforward sequential synthetic strategy has been developed for the synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of the Escherichia albertii O4 strain in very good yield with the desired configuration at the glycosidic linkages using thioglycosides an...

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Autores principales: Manna, Tapasi, Gucchait, Arin, Misra, Anup Kumar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7006483/
https://www.ncbi.nlm.nih.gov/pubmed/32082429
http://dx.doi.org/10.3762/bjoc.16.12
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author Manna, Tapasi
Gucchait, Arin
Misra, Anup Kumar
author_facet Manna, Tapasi
Gucchait, Arin
Misra, Anup Kumar
author_sort Manna, Tapasi
collection PubMed
description A straightforward sequential synthetic strategy has been developed for the synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of the Escherichia albertii O4 strain in very good yield with the desired configuration at the glycosidic linkages using thioglycosides and trichloroacetimidate derivatives as glycosyl donors and perchloric acid supported over silica (HClO(4)/SiO(2)) as a solid supported protic acid glycosyl activator. The expected configuration at the glycosidic linkages was achieved using a reasonable selection of protecting groups in the manosaccharide intermediates.
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spelling pubmed-70064832020-02-20 Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4 Manna, Tapasi Gucchait, Arin Misra, Anup Kumar Beilstein J Org Chem Full Research Paper A straightforward sequential synthetic strategy has been developed for the synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of the Escherichia albertii O4 strain in very good yield with the desired configuration at the glycosidic linkages using thioglycosides and trichloroacetimidate derivatives as glycosyl donors and perchloric acid supported over silica (HClO(4)/SiO(2)) as a solid supported protic acid glycosyl activator. The expected configuration at the glycosidic linkages was achieved using a reasonable selection of protecting groups in the manosaccharide intermediates. Beilstein-Institut 2020-01-22 /pmc/articles/PMC7006483/ /pubmed/32082429 http://dx.doi.org/10.3762/bjoc.16.12 Text en Copyright © 2020, Manna et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Manna, Tapasi
Gucchait, Arin
Misra, Anup Kumar
Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4
title Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4
title_full Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4
title_fullStr Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4
title_full_unstemmed Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4
title_short Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4
title_sort convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall o-antigen of escherichia albertii o4
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7006483/
https://www.ncbi.nlm.nih.gov/pubmed/32082429
http://dx.doi.org/10.3762/bjoc.16.12
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