Synthesis of branched and linear 1,4-linked galactan oligosaccharides
(2018) In Organic and Biomolecular Chemistry 16(7). p.1157-1162- 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.
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- author
- publishing date
- 2018
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Organic and Biomolecular Chemistry
- volume
- 16
- issue
- 7
- pages
- 6 pages
- publisher
- Royal Society of Chemistry
- external identifiers
-
- scopus:85042163352
- pmid:29367995
- ISSN
- 1477-0520
- DOI
- 10.1039/c7ob03035e
- language
- English
- LU publication?
- no
- additional info
- Publisher Copyright: © The Royal Society of Chemistry 2018.
- id
- 366d3ca6-0c31-446e-992a-38ce6c43f58e
- date added to LUP
- 2022-04-08 08:56:36
- date last changed
- 2024-03-17 00:51:13
@article{366d3ca6-0c31-446e-992a-38ce6c43f58e, abstract = {{<p>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.</p>}}, author = {{Andersen, Mathias C.F. and Boos, Irene and Kinnaert, Christine and Awan, Shahid I. and Pedersen, Henriette L. and Kračun, Stjepan K. and Lanz, Gyrithe and Rydahl, Maja G. and Kjærulff, Louise and Håkansson, Maria and Kimbung, Raymond and Logan, Derek T. and Gotfredsen, Charlotte H. and Willats, William G.T. and Clausen, Mads H.}}, issn = {{1477-0520}}, language = {{eng}}, number = {{7}}, pages = {{1157--1162}}, publisher = {{Royal Society of Chemistry}}, series = {{Organic and Biomolecular Chemistry}}, title = {{Synthesis of branched and linear 1,4-linked galactan oligosaccharides}}, url = {{http://dx.doi.org/10.1039/c7ob03035e}}, doi = {{10.1039/c7ob03035e}}, volume = {{16}}, year = {{2018}}, }