GL-3702

alpha2,3-sialyl-tri-LacNAc is a heptasaccharide comprising three N-acetyllactosamine repeats which are covalently linked by two beta1,3-glycosidic linkages. The non-reducing galactose is modified with an alpha-linked sialic acid at the 3-position and the anomeric R-group can represent either an aminopentanol linker or an aminopentanol conjugated to biotin.

Compound name(s): α2,3-sialyl-tri-LacNAc, α2,3-sialyl-LacNAc-LacNAc-LacNAc, 3’SLn3 bearing an aminopentanol anomeric linker.

Anomeric linker:  5-amino-1-pentanol

Chemical formula: C58H98N5O39Na

Physical state of bulk product:  White, fluffy solid

Molar mass:  1,512.40

Compound information:  Extended poly-N-acetyllactosamine (poly-LacNAc) chains are a common feature of highly branched N-glycans, and their elongation is frequently increased on the cell surface in several cancers. Capped with an α2,3-linked sialic acid, this tri-LacNAc structure mimics extended ligands recognized by selectins and siglecs, and also serves as a ligand for galectins, a protein family implicated in immune regulation and cell adhesion.  Extended sialylated poly-LacNAc structures have been shown to have increased affinity for certain influenza hemagglutinins compared to their less elongated counterparts.  This compound is useful for studying how poly-LacNAc chain length affects binding for these carbohydrate-recognizing proteins.

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QC report for GL-3702

References (links open in a new tab):

1. Nycholat, C.M., McBride, R., Ekiert, D.C., Xu, R., Rangarajan, J., Peng, W., Razi, N., Gilbert, M., Wakarchuk, W., Wilson, I.A. and Paulson, J.C. Recognition of Sialylated Poly-N-acetyllactosamine Chains on N- and O-Linked Glycans by Human and Avian Influenza A Virus Hemagglutinins. Angew. Chem. Int.  Ed. 2012, 51, 4860-4863.

2. Stowell S, Arthur C, Mehta P, Slanina K, Blixt O, Leffler H, Smith D, Cummings R. Galectin-1, -2, and -3 Exhibit Differential Recognition of Sialylated Glycans and Blood Group Antigens Journal of Biological Chemistry, 2008, 283, 10109-10123.