Efficient enzymatic synthesis of the sialyl-Lewisx tetrasaccharide. A ligand for selectin-type adhesion molecules.
Sialyl-Lewisx (NeuAc alpha 2-->3Gal beta 1-->4[Fuc alpha 1-->3]GlcNAc] has been identified as a ligand for E-selectin, P-selectin and recently also for L-selectin. We have synthesized the sialyl-Lewisx tetrasaccharide by total enzymatic synthesis from N-acetyllactosamine using a placental alpha 2-->3-sialyltransferase specific for type-2 chain acceptors, followed by a cloned human alpha 1-->3-fucosyltransferase (FucTV, the 'plasma-type' enzyme). This procedure resulted in the tetrasaccharide in a 61% overall yield.
de Vries
T
T
Department of Medical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands.
van den Eijnden
D H
DH
Schultz
J
J
O'Neill
R
R
D000606:Amino Sugars / Q000378:metabolism; D002240:Carbohydrate Sequence; D002448:Cell Adhesion; D015815:Cell Adhesion Molecules / Q000378:metabolism*; D002478:Cells, Cultured; D019040:E-Selectin; D005647:Fucosyltransferases / Q000378:metabolism; D006801:Humans; D016256:Lewis X Antigen / Q000737:chemistry* / Q000378:metabolism; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000378:metabolism; D012799:Sialyltransferases / Q000378:metabolism
D000606:Amino Sugars; D015815:Cell Adhesion Molecules; D019040:E-Selectin; D016256:Lewis X Antigen; D009844:Oligosaccharides; C000458:N-acetyllactosamine; D005647:Fucosyltransferases; D012799:Sialyltransferases