First and Stereoselective Synthesis of an α-(2→5)-Linked Disaccharide of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo)

[Image: see text] Resistance of bacterial pathogens toward antibiotics has revived interest in lipopolysaccharide (LPS) motifs as potential therapeutic targets. The LPS of several pathogenic Acinetobacter strains comprises a 4,5-branched Kdo trisaccharide containing an uncommon (2→5)-linkage. In thi...

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Autores principales: Pokorny, Barbara, Kosma, Paul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4284650/
https://www.ncbi.nlm.nih.gov/pubmed/25496419
http://dx.doi.org/10.1021/ol5033128
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author Pokorny, Barbara
Kosma, Paul
author_facet Pokorny, Barbara
Kosma, Paul
author_sort Pokorny, Barbara
collection PubMed
description [Image: see text] Resistance of bacterial pathogens toward antibiotics has revived interest in lipopolysaccharide (LPS) motifs as potential therapeutic targets. The LPS of several pathogenic Acinetobacter strains comprises a 4,5-branched Kdo trisaccharide containing an uncommon (2→5)-linkage. In this contribution the first stereoselective glycosylation method for obtaining an α-Kdo-(2→5)-α-Kdo disaccharide in good yield is highlighted. The synthetic approach used for accessing this linkage type will allow for future studies of the immunoreactivity associated with this unique bacterial Kdo inner core structure.
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spelling pubmed-42846502015-01-07 First and Stereoselective Synthesis of an α-(2→5)-Linked Disaccharide of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo) Pokorny, Barbara Kosma, Paul Org Lett [Image: see text] Resistance of bacterial pathogens toward antibiotics has revived interest in lipopolysaccharide (LPS) motifs as potential therapeutic targets. The LPS of several pathogenic Acinetobacter strains comprises a 4,5-branched Kdo trisaccharide containing an uncommon (2→5)-linkage. In this contribution the first stereoselective glycosylation method for obtaining an α-Kdo-(2→5)-α-Kdo disaccharide in good yield is highlighted. The synthetic approach used for accessing this linkage type will allow for future studies of the immunoreactivity associated with this unique bacterial Kdo inner core structure. American Chemical Society 2014-12-12 2015-01-02 /pmc/articles/PMC4284650/ /pubmed/25496419 http://dx.doi.org/10.1021/ol5033128 Text en Copyright © 2014 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Pokorny, Barbara
Kosma, Paul
First and Stereoselective Synthesis of an α-(2→5)-Linked Disaccharide of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo)
title First and Stereoselective Synthesis of an α-(2→5)-Linked Disaccharide of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo)
title_full First and Stereoselective Synthesis of an α-(2→5)-Linked Disaccharide of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo)
title_fullStr First and Stereoselective Synthesis of an α-(2→5)-Linked Disaccharide of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo)
title_full_unstemmed First and Stereoselective Synthesis of an α-(2→5)-Linked Disaccharide of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo)
title_short First and Stereoselective Synthesis of an α-(2→5)-Linked Disaccharide of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo)
title_sort first and stereoselective synthesis of an α-(2→5)-linked disaccharide of 3-deoxy-d-manno-oct-2-ulosonic acid (kdo)
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4284650/
https://www.ncbi.nlm.nih.gov/pubmed/25496419
http://dx.doi.org/10.1021/ol5033128
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