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

Mathias C.F. Andersen; Irene Boos; Christine Kinnaert; Shahid I. Awan; Henriette Lodberg Pedersen; Stjepan Kresimir Kračun; Gyrithe Lanz; Maja Gro Rydahl; Louise Kjærulff; Maria Håkansson; Raymond Kimbung; Derek T. Logan; Charlotte H. Gotfredsen; William G.T. Willats; Mads H. Clausen

doi:10.1039/c7ob03035e

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

Mathias C.F. Andersen, Irene Boos, Christine Kinnaert, Shahid I. Awan, Henriette Lodberg Pedersen, Stjepan Kresimir Kračun, Gyrithe Lanz, Maja Gro Rydahl, Louise Kjærulff, Maria Håkansson, Raymond Kimbung, Derek T. Logan, Charlotte H. Gotfredsen, William G.T. Willats, Mads H. Clausen^*

^*Corresponding author af dette arbejde

Planteglycobiologi

1 Citationer (Scopus)

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.

Originalsprog	Engelsk
Tidsskrift	Organic and Biomolecular Chemistry
Vol/bind	16
Udgave nummer	7
Sider (fra-til)	1157-1162
Antal sider	6
ISSN	1477-0520
DOI	https://doi.org/10.1039/c7ob03035e
Status	Udgivet - 2018

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10.1039/c7ob03035e

Citationsformater

Andersen, M. C. F., Boos, I., Kinnaert, C., Awan, S. I., Pedersen, H. L., Kračun, S. K., Lanz, G., Rydahl, M. G., Kjærulff, L., Håkansson, M., Kimbung, R., Logan, D. T., Gotfredsen, C. H., Willats, W. G. T., & Clausen, M. H. (2018). Synthesis of branched and linear 1,4-linked galactan oligosaccharides. Organic and Biomolecular Chemistry, 16(7), 1157-1162. https://doi.org/10.1039/c7ob03035e

@article{331886cba1e74d5a9032e0d9a6a71105,

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

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.",

author = "Andersen, {Mathias C.F.} and Irene Boos and Christine Kinnaert and Awan, {Shahid I.} and Pedersen, {Henriette Lodberg} and Kra{\v c}un, {Stjepan Kresimir} and Gyrithe Lanz and Rydahl, {Maja Gro} and Louise Kj{\ae}rulff and Maria H{\aa}kansson and Raymond Kimbung and Logan, {Derek T.} and Gotfredsen, {Charlotte H.} and Willats, {William G.T.} and Clausen, {Mads H.}",

year = "2018",

doi = "10.1039/c7ob03035e",

language = "English",

volume = "16",

pages = "1157--1162",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1470-4358",

publisher = "Royal Society of Chemistry",

number = "7",

}

TY - JOUR

T1 - Synthesis of branched and linear 1,4-linked galactan oligosaccharides

AU - Andersen, Mathias C.F.

AU - Boos, Irene

AU - Kinnaert, Christine

AU - Awan, Shahid I.

AU - Pedersen, Henriette Lodberg

AU - Kračun, Stjepan Kresimir

AU - Lanz, Gyrithe

AU - Rydahl, Maja Gro

AU - Kjærulff, Louise

AU - Håkansson, Maria

AU - Kimbung, Raymond

AU - Logan, Derek T.

AU - Gotfredsen, Charlotte H.

AU - Willats, William G.T.

AU - Clausen, Mads H.

PY - 2018

Y1 - 2018

N2 - 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.

AB - 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.

U2 - 10.1039/c7ob03035e

DO - 10.1039/c7ob03035e

M3 - Journal article

C2 - 29367995

AN - SCOPUS:85042163352

SN - 1470-4358

VL - 16

SP - 1157

EP - 1162

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 7

ER -

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

Abstract

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