316810-10-3Relevant academic research and scientific papers
Synthesis and glycan priming activity of acetylated disaccharides
Sarkar, Arun K,Brown, Jillian R,Esko, Jeffrey D
, p. 287 - 300 (2007/10/03)
Five disaccharides related in structure to the glycans of vertebrate mucins have been chemically synthesized using orthogonal blocking, coupling and deblocking techniques. These include 2-naphthylmethyl 3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1 → 4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside (6), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1 → 3)-2,4,6-tri-O-acetyl-β-D-galactopyranoside (14), 2-naphthylmethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1 → 3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-galactopyranoside (20), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1 → 3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-galactopyranoside (23) and 2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1 → 6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranoside (27). These per-O-acetylated compounds were fed to U-937 cells to test their ability to prime oligosaccharide synthesis, inhibit glycoprotein biosynthesis and alter adhesion to E-selectin expressed on endothelial cells. The results show that 6, 14, and 20 served as substrates for oligosaccharide synthesis. The generation of glycoside-primed glycans altered the formation of glycoproteins on the cell surface and inhibited cell adhesion dependent on E-selectin. (C) 2000 Elsevier Science Ltd.
