Synthesis of 3-O- and 4-O-(2-aminoethylphosphono) derivatives of methyl l-glycero-α-d-manno-heptopyranoside

ABSTRACT: Phosphoethanolamine derivatives of the bacterial saccharide l-glycero-d-manno-heptose have been prepared using a phosphoramidite-based coupling reaction at position 4 of a side-chain-protected 2,3-O-orthoester methyl heptoside and at position 3 of a 3,4-diol heptoside, respectively. Global...

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Detalles Bibliográficos
Autores principales: Walter, Martin, Kohout, Claudia, Blaukopf, Markus, Kosma, Paul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2016
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5225220/
https://www.ncbi.nlm.nih.gov/pubmed/28127097
http://dx.doi.org/10.1007/s00706-016-1868-6
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author Walter, Martin
Kohout, Claudia
Blaukopf, Markus
Kosma, Paul
author_facet Walter, Martin
Kohout, Claudia
Blaukopf, Markus
Kosma, Paul
author_sort Walter, Martin
collection PubMed
description ABSTRACT: Phosphoethanolamine derivatives of the bacterial saccharide l-glycero-d-manno-heptose have been prepared using a phosphoramidite-based coupling reaction at position 4 of a side-chain-protected 2,3-O-orthoester methyl heptoside and at position 3 of a 3,4-diol heptoside, respectively. Global deprotection afforded the corresponding 2-aminoethylphosphodiester derivatives as substrates for crystallographic and binding studies with lectins and antibodies targeting the inner core structure of bacterial lipopolysaccharides. GRAPHICAL ABSTRACT: [Image: see text]
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spelling pubmed-52252202017-01-24 Synthesis of 3-O- and 4-O-(2-aminoethylphosphono) derivatives of methyl l-glycero-α-d-manno-heptopyranoside Walter, Martin Kohout, Claudia Blaukopf, Markus Kosma, Paul Monatsh Chem Original Paper ABSTRACT: Phosphoethanolamine derivatives of the bacterial saccharide l-glycero-d-manno-heptose have been prepared using a phosphoramidite-based coupling reaction at position 4 of a side-chain-protected 2,3-O-orthoester methyl heptoside and at position 3 of a 3,4-diol heptoside, respectively. Global deprotection afforded the corresponding 2-aminoethylphosphodiester derivatives as substrates for crystallographic and binding studies with lectins and antibodies targeting the inner core structure of bacterial lipopolysaccharides. GRAPHICAL ABSTRACT: [Image: see text] Springer Vienna 2016-12-08 2017 /pmc/articles/PMC5225220/ /pubmed/28127097 http://dx.doi.org/10.1007/s00706-016-1868-6 Text en © The Author(s) 2016 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
spellingShingle Original Paper
Walter, Martin
Kohout, Claudia
Blaukopf, Markus
Kosma, Paul
Synthesis of 3-O- and 4-O-(2-aminoethylphosphono) derivatives of methyl l-glycero-α-d-manno-heptopyranoside
title Synthesis of 3-O- and 4-O-(2-aminoethylphosphono) derivatives of methyl l-glycero-α-d-manno-heptopyranoside
title_full Synthesis of 3-O- and 4-O-(2-aminoethylphosphono) derivatives of methyl l-glycero-α-d-manno-heptopyranoside
title_fullStr Synthesis of 3-O- and 4-O-(2-aminoethylphosphono) derivatives of methyl l-glycero-α-d-manno-heptopyranoside
title_full_unstemmed Synthesis of 3-O- and 4-O-(2-aminoethylphosphono) derivatives of methyl l-glycero-α-d-manno-heptopyranoside
title_short Synthesis of 3-O- and 4-O-(2-aminoethylphosphono) derivatives of methyl l-glycero-α-d-manno-heptopyranoside
title_sort synthesis of 3-o- and 4-o-(2-aminoethylphosphono) derivatives of methyl l-glycero-α-d-manno-heptopyranoside
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5225220/
https://www.ncbi.nlm.nih.gov/pubmed/28127097
http://dx.doi.org/10.1007/s00706-016-1868-6
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