Synthesis of the saccharide moiety of galactosylgloboside (SSEA-3) and its conjugation to bovine serum albumin and sepharose

✍ Scribed by Ulf Nilsson; Göran Magnusson

• Book ID: 102990497
• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 484 KB
• Volume: 272
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00044-t

✦ Synopsis

The pentasaccharide glycoside corresponding to galactosylgloboside (SSEA-3), fl-D-Galp-(1 4), was synthesized via glycosylation (87%) of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-

glucopyranoside (2) with the glycosyl donor methyl 4,6-di-O-acetyl-2-deoxy-2-phthalimido-3-O-(2,3,4,6-tetra-O-acetyl-[3-o-galactopyranosyl)-l-thio-fl-o-galactopyranoside (1), followed by removal of protecting groups. Compound 4 was transformed into the spacer glycoside fl-o-Galp-(1 3)-fl-o-GalpNAc-(1 ~ 3)-a-D-Galp-(1 ~ 4)-/3-D-Galp-(1 ~ 4)-fl-D-Glcp-I-SCHECHECOOH (10), which was coupled to bovine serum albumin (BSA), and Sepharose beads, to give the corresponding neoglycoprotein (11, 6 mol of saccharide/mol of BSA) and glycosylated Sepharose (12, 2.7/.~mol of saccharide/mL of sedimented beads), respectively. An improved synthesis of a protected globotetraoside fl-o-GalpNAc-(1 -~ 3)-a-o-Galp-(1 -* 4)-fl-o-Galp-(1 ~ 4)-/3-D-Glcp-1-OCHECH2SiMe 3 is also reported.