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Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O‐Polysaccharide of Enterotoxigenic Escherichia coli O139
Enterotoxigenic Escherichia coli (ETEC) like the O139 strain are mostly responsible for traveler's diarrhea and causes diseases in pigs, cattle, and poultry. A convenient synthetic strategy was developed for the synthesis of the heptasaccharide repeating unit of the cell wall lipopolysaccharide...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4906484/ https://www.ncbi.nlm.nih.gov/pubmed/27308210 http://dx.doi.org/10.1002/open.201500164 |
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author | Ghosh, Tamashree Misra, Anup Kumar |
author_facet | Ghosh, Tamashree Misra, Anup Kumar |
author_sort | Ghosh, Tamashree |
collection | PubMed |
description | Enterotoxigenic Escherichia coli (ETEC) like the O139 strain are mostly responsible for traveler's diarrhea and causes diseases in pigs, cattle, and poultry. A convenient synthetic strategy was developed for the synthesis of the heptasaccharide repeating unit of the cell wall lipopolysaccharide of the E. coli O139 strain. The p‐methoxybenzyl (PMB) group was used as a temporary protecting group which was removed in situ under the glycosylation conditions by changing the reaction temperature during the synthesis of the target compound. All glycosylation steps gave high yields with good stereoselectivity. A (2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl (TEMPO)‐mediated selective oxidation of the primary hydroxyl group was carried out using a biphasic reaction condition at the late stage of the synthesis. Such synthetic oligosaccharides could later be effectively conjugated with proteins to prepare glycoconjugate derivatives as vaccine candidates. |
format | Online Article Text |
id | pubmed-4906484 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-49064842016-06-15 Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O‐Polysaccharide of Enterotoxigenic Escherichia coli O139 Ghosh, Tamashree Misra, Anup Kumar ChemistryOpen Communications Enterotoxigenic Escherichia coli (ETEC) like the O139 strain are mostly responsible for traveler's diarrhea and causes diseases in pigs, cattle, and poultry. A convenient synthetic strategy was developed for the synthesis of the heptasaccharide repeating unit of the cell wall lipopolysaccharide of the E. coli O139 strain. The p‐methoxybenzyl (PMB) group was used as a temporary protecting group which was removed in situ under the glycosylation conditions by changing the reaction temperature during the synthesis of the target compound. All glycosylation steps gave high yields with good stereoselectivity. A (2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl (TEMPO)‐mediated selective oxidation of the primary hydroxyl group was carried out using a biphasic reaction condition at the late stage of the synthesis. Such synthetic oligosaccharides could later be effectively conjugated with proteins to prepare glycoconjugate derivatives as vaccine candidates. John Wiley and Sons Inc. 2015-08-12 /pmc/articles/PMC4906484/ /pubmed/27308210 http://dx.doi.org/10.1002/open.201500164 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Communications Ghosh, Tamashree Misra, Anup Kumar Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O‐Polysaccharide of Enterotoxigenic Escherichia coli O139 |
title | Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O‐Polysaccharide of Enterotoxigenic Escherichia coli O139 |
title_full | Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O‐Polysaccharide of Enterotoxigenic Escherichia coli O139 |
title_fullStr | Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O‐Polysaccharide of Enterotoxigenic Escherichia coli O139 |
title_full_unstemmed | Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O‐Polysaccharide of Enterotoxigenic Escherichia coli O139 |
title_short | Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O‐Polysaccharide of Enterotoxigenic Escherichia coli O139 |
title_sort | synthesis of the heptasaccharide repeating unit of the cell wall o‐polysaccharide of enterotoxigenic escherichia coli o139 |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4906484/ https://www.ncbi.nlm.nih.gov/pubmed/27308210 http://dx.doi.org/10.1002/open.201500164 |
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