Glycosyltransferase catalyzed assemblage of sialyl-Lewis(a)-saccharopeptides.
A series of methyl hexopyranosiduronic acids are coupled to type I disaccharide amines to give 'trisaccharides' which have the natural N-acetyl group of the type I disaccharides replaced by uronic acids (-->saccharopeptides). These saccharopeptides are surprisingly good substrates for alpha-2,3,-sialyltransferase and fucosyltransferase III. The enzymes transfer N-acetylneuraminic acid and fucose, respectively, onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to yield sialyl-Lewis(a)-saccharopeptides.
Baisch
G
G
Novartis Pharma AG, Basle, Switzerland.
Ohrlein
R
R
D018395:CA-19-9 Antigen; D002240:Carbohydrate Sequence; D002384:Catalysis; D005732:Gangliosides / Q000378:metabolism*; D016695:Glycosyltransferases / Q000378:metabolism*; D006801:Humans; D007983:Lewis Blood Group Antigens / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000378:metabolism*; D009844:Oligosaccharides / Q000378:metabolism; D000080506:Sialyl Lewis X Antigen; D014574:Uronic Acids / Q000378:metabolism
D018395:CA-19-9 Antigen; D005732:Gangliosides; D007983:Lewis Blood Group Antigens; D009842:Oligopeptides; D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen; D014574:Uronic Acids; C064564:sialyl Le(a) ganglioside; D016695:Glycosyltransferases