Chemoenzymatic Synthesis of Sialyl-Trimeric-Lewis X

✍ Scribed by Kathryn M. Koeller; Chi-Huey Wong

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 205 KB
• Volume: 6
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/(sici)1521-3765(20000403)6:7<1243::aid-chem1243>3.0.co;2-j

✦ Synopsis

The decasaccharide sialyl-trimeric-Lewis x is a component of glycoproteins and glycolipids that serve as E-and P-selectin ligands. The synthesis of this target structure was accomplished by utilizing a combination of chemical and enzymatic methods. Highlights of the chemical synthesis include minimal use of protecting groups and regioselective glycosylations to arrive at a linear tri-lactosamine structure. Glycosyltransferase-catalyzed reactions were then employed for the addition of the terminal sialic acid and branch-point fucose residues. Notably, fucosyltransferases V and VI showed different specificities for the sialyl-tri-lactosamine core structure.