Synthesis of galactomannan fragments to help NMR assignment of polysaccharides extracted from lichens

David, Louis-Philippe; Ferron, Solenn; Favreau, Bénédicte; Yeni, Oznur; Ollivier, Simon; Ropartz, David; Compagnon, Isabelle; Ferrières, Vincent; Le Dévéhat, Françoise; Legentil, Laurent

doi:10.1039/d4ob00047a

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00047a

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Synthesis of galactomannan fragments to help NMR assignment of polysaccharides extracted from lichens

Louis-Philippe David,

Solenn Ferron,

Bénédicte Favreau

et al.

Abstract: The synthesis of six model trisaccharides representative of galactomannans produced by lichens was performed thanks to regioselective glycosylation. These standards include linear and branched galactomannans bearing either galactofuranosyl or galactopyranosyl...

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Acid-Catalyzed Transformation of Pyranosides into Furanosides as a Tool for Preparation of Furanoside Synthetic Blocks

Argunov,

Aladysheva,

Krylov

et al. 2024

Org. Lett.

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The importance of natural glycoconjugates containing furanoside residues causes a continued demand for the development of efficient methods for the synthesis of corresponding oligosaccharide derivatives to be used as molecular probes in glycobiological studies. Currently, the chemical synthesis of furanose-containing oligosaccharides often represents a significant challenge because of the lack of short, efficient, and reliable methods for the preparation of selectively substituted furanoside blocks. Herein, we report an easy protocol toward galactofuranosecontaining molecules based on the unusual equilibrium between pyranoside and furanoside forms observed for a series of substituted galactosides. The method's utility is illustrated by the syntheses of furanoside-containing oligosaccharides related to the antigenic polysaccharides of Aspergillus fumigatus and Klebsiella pneumoniae O2ac.

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Acid-Catalyzed Transformation of Pyranosides into Furanosides as a Tool for Preparation of Furanoside Synthetic Blocks

Argunov,

Aladysheva,

Krylov

et al. 2024

Org. Lett.

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Synthesis of galactomannan fragments to help NMR assignment of polysaccharides extracted from lichens

Abstract: The synthesis of six model trisaccharides representative of galactomannans produced by lichens was performed thanks to regioselective glycosylation. These standards include linear and branched galactomannans bearing either galactofuranosyl or galactopyranosyl...

Cited by 1 publication

References 23 publications

Acid-Catalyzed Transformation of Pyranosides into Furanosides as a Tool for Preparation of Furanoside Synthetic Blocks

Acid-Catalyzed Transformation of Pyranosides into Furanosides as a Tool for Preparation of Furanoside Synthetic Blocks

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