Synthesis of branched and linear 1,4-linked galactan oligosaccharides

Mathias C. Franch Andersen, Irene Boos, Christine Kinnaert, Shahid Iqbal Awan, Henriette L. Pedersen, Stjepan K Kracun, Gyrithe Lanz, Maja G Rydahl, Louise Kjærulff, Maria Håkansson, Raymond Kimbung, Derek Logan, Charlotte Held Gotfredsen, William George Tycho Willats, Mads Hartvig Hartvig Clausen*

*Corresponding author for this work

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Abstract

We report the synthesis of linear and branched (1→4)-D-galactans. Four tetra- and one pentasaccharide were accessed by adopting a procedure of regioselective ring opening of a 4,6-O-naphthylidene protecting group followed by glycosylation using phenyl thioglycoside donros. The binding of the linear pentasaccharide with galectin-3 is also investigated by determination of a co-crystal structure. The binding of the (1→4)-linked galactan to Gal-3 highlights oligosaccharides of pectic galactan, which is abundant in the human diet, as putative Gal-3 ligands.
Original languageEnglish
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number7
Pages (from-to)1157-1162
ISSN1477-0520
DOIs
Publication statusPublished - 2018

Keywords

  • Plant oligosaccharides
  • RG-I, (1→4)-D-galactan
  • CRD
  • Galectin-3

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