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Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside
The total chemical synthesis of the pentasaccharide repeating unit of the O-polysaccharide from E. coli O132 is accomplished in the form of its 2-aminoethyl glycoside. The 2-aminoethyl glycoside is particularly important as it allows further glycoconjugate formation utilizing the terminal amine with...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Beilstein-Institut
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6839562/ https://www.ncbi.nlm.nih.gov/pubmed/31728170 http://dx.doi.org/10.3762/bjoc.15.249 |
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author | Pal, Debasish Mukhopadhyay, Balaram |
author_facet | Pal, Debasish Mukhopadhyay, Balaram |
author_sort | Pal, Debasish |
collection | PubMed |
description | The total chemical synthesis of the pentasaccharide repeating unit of the O-polysaccharide from E. coli O132 is accomplished in the form of its 2-aminoethyl glycoside. The 2-aminoethyl glycoside is particularly important as it allows further glycoconjugate formation utilizing the terminal amine without affecting the stereochemistry of the reducing end. The target was achieved through a [3 + 2] strategy where the required monosaccharide building blocks are prepared from commercially available sugars through rational protecting group manipulation. The NIS-mediated activation of thioglycosides was used extensively for the glycosylation reactions throughout. |
format | Online Article Text |
id | pubmed-6839562 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-68395622019-11-14 Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside Pal, Debasish Mukhopadhyay, Balaram Beilstein J Org Chem Full Research Paper The total chemical synthesis of the pentasaccharide repeating unit of the O-polysaccharide from E. coli O132 is accomplished in the form of its 2-aminoethyl glycoside. The 2-aminoethyl glycoside is particularly important as it allows further glycoconjugate formation utilizing the terminal amine without affecting the stereochemistry of the reducing end. The target was achieved through a [3 + 2] strategy where the required monosaccharide building blocks are prepared from commercially available sugars through rational protecting group manipulation. The NIS-mediated activation of thioglycosides was used extensively for the glycosylation reactions throughout. Beilstein-Institut 2019-10-28 /pmc/articles/PMC6839562/ /pubmed/31728170 http://dx.doi.org/10.3762/bjoc.15.249 Text en Copyright © 2019, Pal and Mukhopadhyay 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 Pal, Debasish Mukhopadhyay, Balaram Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside |
title | Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside |
title_full | Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside |
title_fullStr | Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside |
title_full_unstemmed | Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside |
title_short | Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside |
title_sort | chemical synthesis of the pentasaccharide repeating unit of the o-specific polysaccharide from escherichia coli o132 in the form of its 2-aminoethyl glycoside |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6839562/ https://www.ncbi.nlm.nih.gov/pubmed/31728170 http://dx.doi.org/10.3762/bjoc.15.249 |
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