Chemoenzymatic Synthesis of Sialyl-Trimeric-Lewis X

• Published in: Chemistry : a European journal Vol. 6; no. 7; pp. 1243 - 1251
• Main Authors: Koeller, Kathryn M., Wong, Chi-Huey
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 03.04.2000; WILEY‐VCH Verlag
• Subjects: Carbohydrate Conformation; Carbohydrate Sequence; chemoenzymatic synthesis; E-Selectin; Fucosyltransferases - chemistry; Glycosylation; Glycosyltransferases - chemistry; Lewis Blood-Group System; Lewis X Antigen - chemistry; Ligands; Magnetic Resonance Spectroscopy - methods; Molecular Sequence Data; Molecular Structure; oligosaccharides; Oligosaccharides - chemical synthesis; Oligosaccharides - chemistry; P-Selectin; Polysaccharides - chemical synthesis; Polysaccharides - chemistry; regioselective glycosylation; selectin; sialyl Lewis x; Substrate Specificity
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/(SICI)1521-3765(20000403)6:7<1243::AID-CHEM1243>3.0.CO;2-J

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.