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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2020
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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. |
format | Online Article Text |
id | pubmed-7006483 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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