Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae

A pentasaccharide repeating unit containing α-linked D-glucuronic acid, β-linked D-mannose, corresponding to the repeating unit of biofilms produced by Klebsiella pneumoniae, has been synthesized using a stereoselective [2 + 3] convergent glycosylation strategy. The β-D-mannosidic moiety has been sy...

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Autores principales: Gucchait, Arin, Ghosh, Angana, Misra, Anup Kumar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6404407/
https://www.ncbi.nlm.nih.gov/pubmed/30873227
http://dx.doi.org/10.3762/bjoc.15.37
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author Gucchait, Arin
Ghosh, Angana
Misra, Anup Kumar
author_facet Gucchait, Arin
Ghosh, Angana
Misra, Anup Kumar
author_sort Gucchait, Arin
collection PubMed
description A pentasaccharide repeating unit containing α-linked D-glucuronic acid, β-linked D-mannose, corresponding to the repeating unit of biofilms produced by Klebsiella pneumoniae, has been synthesized using a stereoselective [2 + 3] convergent glycosylation strategy. The β-D-mannosidic moiety has been synthesized using a D-mannose-derived thioglycoside by a two-step activation process. Late stage TEMPO-mediated oxidation of the pentasaccharide derivative using phase-transfer reaction conditions furnished the target compound in satisfactory yield.
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spelling pubmed-64044072019-03-14 Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae Gucchait, Arin Ghosh, Angana Misra, Anup Kumar Beilstein J Org Chem Full Research Paper A pentasaccharide repeating unit containing α-linked D-glucuronic acid, β-linked D-mannose, corresponding to the repeating unit of biofilms produced by Klebsiella pneumoniae, has been synthesized using a stereoselective [2 + 3] convergent glycosylation strategy. The β-D-mannosidic moiety has been synthesized using a D-mannose-derived thioglycoside by a two-step activation process. Late stage TEMPO-mediated oxidation of the pentasaccharide derivative using phase-transfer reaction conditions furnished the target compound in satisfactory yield. Beilstein-Institut 2019-02-13 /pmc/articles/PMC6404407/ /pubmed/30873227 http://dx.doi.org/10.3762/bjoc.15.37 Text en Copyright © 2019, Gucchait 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
Gucchait, Arin
Ghosh, Angana
Misra, Anup Kumar
Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae
title Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae
title_full Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae
title_fullStr Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae
title_full_unstemmed Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae
title_short Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae
title_sort convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by klebsiella pneumoniae
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6404407/
https://www.ncbi.nlm.nih.gov/pubmed/30873227
http://dx.doi.org/10.3762/bjoc.15.37
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