Cargando…

Synthesis of α-d-glucosyl substituted methyl glycosides of 3-deoxy-α-d-manno- and d-glycero-α-d-talo-oct-2-ulosonic acid (Kdo/Ko) corresponding to inner core fragments of Acinetobacter lipopolysaccharide

The α-d-glucopyranosyl-(1→5)-substituted methyl glycosides of 3-deoxy-α-d-manno-oct-2-ulosonic acid (Kdo), 3-deoxy-α-d-lyxo-hept-2-ulosonic acid (Kdh), and d-glycero-α-d-talo-oct-2-ulosonic acid (Ko) were prepared using orthogonally protected glycosyl acceptor derivatives via glycosylation with a to...

Descripción completa

Detalles Bibliográficos
Autores principales: Pokorny, Barbara, Müller-Loennies, Sven, Kosma, Paul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4019464/
https://www.ncbi.nlm.nih.gov/pubmed/24785390
http://dx.doi.org/10.1016/j.carres.2014.03.004
_version_ 1782480165861851136
author Pokorny, Barbara
Müller-Loennies, Sven
Kosma, Paul
author_facet Pokorny, Barbara
Müller-Loennies, Sven
Kosma, Paul
author_sort Pokorny, Barbara
collection PubMed
description The α-d-glucopyranosyl-(1→5)-substituted methyl glycosides of 3-deoxy-α-d-manno-oct-2-ulosonic acid (Kdo), 3-deoxy-α-d-lyxo-hept-2-ulosonic acid (Kdh), and d-glycero-α-d-talo-oct-2-ulosonic acid (Ko) were prepared using orthogonally protected glycosyl acceptor derivatives via glycosylation with a torsionally disarmed 4,6-O-benzylidene protected trifluoroacetimidate glucosyl donor followed by global deprotection. The related 6-O-phosphoryl-α-d-glucopyranosyl-(1→5)-substituted Kdo and Kdh derivatives were derived from a benzylidene-protected glucosyl intermediate using phosphoramidite and phosphoryl chloride-based phosphorylation steps, respectively. The deprotected disaccharides serve as ligands to study lectin binding of Acinetobacter lipopolysaccharide core oligosaccharides.
format Online
Article
Text
id pubmed-4019464
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher Elsevier
record_format MEDLINE/PubMed
spelling pubmed-40194642014-06-04 Synthesis of α-d-glucosyl substituted methyl glycosides of 3-deoxy-α-d-manno- and d-glycero-α-d-talo-oct-2-ulosonic acid (Kdo/Ko) corresponding to inner core fragments of Acinetobacter lipopolysaccharide Pokorny, Barbara Müller-Loennies, Sven Kosma, Paul Carbohydr Res Article The α-d-glucopyranosyl-(1→5)-substituted methyl glycosides of 3-deoxy-α-d-manno-oct-2-ulosonic acid (Kdo), 3-deoxy-α-d-lyxo-hept-2-ulosonic acid (Kdh), and d-glycero-α-d-talo-oct-2-ulosonic acid (Ko) were prepared using orthogonally protected glycosyl acceptor derivatives via glycosylation with a torsionally disarmed 4,6-O-benzylidene protected trifluoroacetimidate glucosyl donor followed by global deprotection. The related 6-O-phosphoryl-α-d-glucopyranosyl-(1→5)-substituted Kdo and Kdh derivatives were derived from a benzylidene-protected glucosyl intermediate using phosphoramidite and phosphoryl chloride-based phosphorylation steps, respectively. The deprotected disaccharides serve as ligands to study lectin binding of Acinetobacter lipopolysaccharide core oligosaccharides. Elsevier 2014-06-04 /pmc/articles/PMC4019464/ /pubmed/24785390 http://dx.doi.org/10.1016/j.carres.2014.03.004 Text en © 2014 The Authors https://creativecommons.org/licenses/by-nc-sa/3.0/This is an open access article under the CC BY-NC-SA license (http://creativecommons.org/licenses/by-nc-sa/3.0/).
spellingShingle Article
Pokorny, Barbara
Müller-Loennies, Sven
Kosma, Paul
Synthesis of α-d-glucosyl substituted methyl glycosides of 3-deoxy-α-d-manno- and d-glycero-α-d-talo-oct-2-ulosonic acid (Kdo/Ko) corresponding to inner core fragments of Acinetobacter lipopolysaccharide
title Synthesis of α-d-glucosyl substituted methyl glycosides of 3-deoxy-α-d-manno- and d-glycero-α-d-talo-oct-2-ulosonic acid (Kdo/Ko) corresponding to inner core fragments of Acinetobacter lipopolysaccharide
title_full Synthesis of α-d-glucosyl substituted methyl glycosides of 3-deoxy-α-d-manno- and d-glycero-α-d-talo-oct-2-ulosonic acid (Kdo/Ko) corresponding to inner core fragments of Acinetobacter lipopolysaccharide
title_fullStr Synthesis of α-d-glucosyl substituted methyl glycosides of 3-deoxy-α-d-manno- and d-glycero-α-d-talo-oct-2-ulosonic acid (Kdo/Ko) corresponding to inner core fragments of Acinetobacter lipopolysaccharide
title_full_unstemmed Synthesis of α-d-glucosyl substituted methyl glycosides of 3-deoxy-α-d-manno- and d-glycero-α-d-talo-oct-2-ulosonic acid (Kdo/Ko) corresponding to inner core fragments of Acinetobacter lipopolysaccharide
title_short Synthesis of α-d-glucosyl substituted methyl glycosides of 3-deoxy-α-d-manno- and d-glycero-α-d-talo-oct-2-ulosonic acid (Kdo/Ko) corresponding to inner core fragments of Acinetobacter lipopolysaccharide
title_sort synthesis of α-d-glucosyl substituted methyl glycosides of 3-deoxy-α-d-manno- and d-glycero-α-d-talo-oct-2-ulosonic acid (kdo/ko) corresponding to inner core fragments of acinetobacter lipopolysaccharide
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4019464/
https://www.ncbi.nlm.nih.gov/pubmed/24785390
http://dx.doi.org/10.1016/j.carres.2014.03.004
work_keys_str_mv AT pokornybarbara synthesisofadglucosylsubstitutedmethylglycosidesof3deoxyadmannoanddglyceroadtalooct2ulosonicacidkdokocorrespondingtoinnercorefragmentsofacinetobacterlipopolysaccharide
AT mullerloenniessven synthesisofadglucosylsubstitutedmethylglycosidesof3deoxyadmannoanddglyceroadtalooct2ulosonicacidkdokocorrespondingtoinnercorefragmentsofacinetobacterlipopolysaccharide
AT kosmapaul synthesisofadglucosylsubstitutedmethylglycosidesof3deoxyadmannoanddglyceroadtalooct2ulosonicacidkdokocorrespondingtoinnercorefragmentsofacinetobacterlipopolysaccharide