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Issue 7, 2018
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Synthesis of branched and linear 1,4-linked galactan oligosaccharides

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Abstract

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.

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

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Supplementary files

Article information


Submitted
07 Dec 2017
Accepted
15 Jan 2018
First published
15 Jan 2018

Org. Biomol. Chem., 2018,16, 1157-1162
Article type
Paper

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

M. C. F. Andersen, I. Boos, C. Kinnaert, S. I. Awan, H. L. Pedersen, S. K. Kračun, G. Lanz, M. G. Rydahl, L. Kjærulff, M. Håkansson, R. Kimbung, D. T. Logan, C. H. Gotfredsen, W. G. T. Willats and M. H. Clausen, Org. Biomol. Chem., 2018, 16, 1157
DOI: 10.1039/C7OB03035E

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