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

The synthesis of six model trisaccharides representative of galactomannans produced by lichens was performed through stereoselective glycosylation. These standards include linear and branched galactomannans bearing either galactofuranosyl or galactopyranosyl entities. The complete assignment of 1 H...

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Published inOrganic & biomolecular chemistry Vol. 22; no. 12; pp. 2395 - 243
Main Authors David, Louis-Philippe, Ferron, Solenn, Favreau, Bénédicte, Yeni, Oznur, Ollivier, Simon, Ropartz, David, Compagnon, Isabelle, Ferrières, Vincent, Le Dévéhat, Françoise, Legentil, Laurent
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 20.03.2024
Royal Society of Chemistry
Subjects
Analytical chemistry
Chemical Sciences
Chemistry
Chemistry, Organic
Ecology, environment
Glycosylation
Lichens
Life Sciences
NMR
Nuclear magnetic resonance
Oligosaccharides
Physical Sciences
Polysaccharides
Saccharides
Science & Technology
Stereoselectivity
Synthesis
IMMUNOLOGICALLY ACTIVE POLYSACCHARIDE
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Summary:The synthesis of six model trisaccharides representative of galactomannans produced by lichens was performed through stereoselective glycosylation. These standards include linear and branched galactomannans bearing either galactofuranosyl or galactopyranosyl entities. The complete assignment of 1 H and 13 C signals for both forms of synthetically reduced oligosaccharides was performed. The resulting NMR data were used to quickly demonstrate the structural characteristics of minor polysaccharides within different extracts of three representative lichens. Straightforward identification of galactomannans from the fractions of lichen extracts using HSQC.
Bibliography:C indexation table of trisaccharides
2D HSQC maps of lichen extracts, and
C NMR spectra of all intermediates and final products. See DOI
1
4-23
13
1-3
https://doi.org/10.1039/d4ob00047a
H and
,
Electronic supplementary information (ESI) available: Experimental procedures and related spectroscopic data for all intermediaries
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00047a