Chemoenzymatic synthesis of sialyl-trimeric-Lewis x.
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.
Koeller
K M
KM
Department of Chemistry, Scripps Research Institute, La Jolla, CA 92037, USA.
Wong
C H
CH
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D019040:E-Selectin; D005647:Fucosyltransferases / Q000737:chemistry; D006031:Glycosylation; D016695:Glycosyltransferases / Q000737:chemistry*; D007983:Lewis Blood Group Antigens; D016256:Lewis X Antigen / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D019007:P-Selectin; D011134:Polysaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D000080506:Sialyl Lewis X Antigen; D013379:Substrate Specificity
D019040:E-Selectin; D007983:Lewis Blood Group Antigens; D016256:Lewis X Antigen; D008024:Ligands; D009844:Oligosaccharides; D019007:P-Selectin; D011134:Polysaccharides; D000080506:Sialyl Lewis X Antigen; C408402:sialyl-trimeric-Lewis X; C107226:tetravalent sialyl Lewis x saccharide; D016695:Glycosyltransferases; D005647:Fucosyltransferases