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Synthesis of branched and linear 1,4-linked galactan oligosaccharides. 2018
Mathias C F Andersen, and
Irene Boos, and
Christine Kinnaert, and
Shahid I Awan, and
Henriette L Pedersen, and
Stjepan K Kračun, and
Gyrithe Lanz, and
Maja G Rydahl, and
Louise Kjærulff, and
Maria Håkansson, and
Raymond Kimbung, and
Derek T Logan, and
Charlotte H Gotfredsen, and
William G T Willats, and
Mads H Clausen
Center for Nanomedicine and Theranostics, Department of Chemistry, Technical University of Denmark, Kemitorvet 207, DK-2800, Kgs. Lyngby, Denmark. mhc@kemi.dtu.dk.
We report the synthesis of linear and branched (1→4)-d-galactans. Four tetrasaccharides 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 donors. The binding of the linear pentasaccharide with galectin-3 is also investigated by the determination of a co-crystal structure. The binding of the (1→4)-linked galactan to Gal-3 highlights the oligosaccharides of pectic galactan, which is abundant in the human diet, as putative Gal-3 ligands.
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