Glycosyl-transferase catalyzed assemblage of sialyl-Lewis(x)-saccharopeptides.
A series of glycohexopyranuronic acids are coupled to glucosamines to give 'disaccharides' which have the natural N-acetyl group of the glcNAc-moiety replaced by various sugar acids (-->saccharopeptides). These saccharopeptides are surprisingly good substrates for beta(1-4)galactosyl-transferase, alpha(2-3)sialyl-transferase, and fucosyl-transferase VI. The enzymes transfer successively galactose, sialic acid, and fucose from the corresponding donors onto these acceptor substrates--despite the far reaching alterations--regio- and stereospecifically in the expected manner to yield a new class of compounds, the sialyl-Lewis(x)-saccharopeptides.
Baisch
G
G
Novartis Pharma AG, Basle, Switzerland.
Ohrlein
R
R
D005643:Fucose; D005647:Fucosyltransferases / Q000737:chemistry / Q000378:metabolism; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D009237:N-Acetyllactosamine Synthase / Q000737:chemistry / Q000378:metabolism*; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D010455:Peptides / Q000737:chemistry* / Q000378:metabolism; D011134:Polysaccharides / Q000737:chemistry* / Q000378:metabolism*; D000080506:Sialyl Lewis X Antigen; D012799:Sialyltransferases / Q000737:chemistry / Q000378:metabolism; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D000094663:beta-Galactoside alpha-2,3-Sialyltransferase
D009844:Oligosaccharides; D010455:Peptides; D011134:Polysaccharides; D000080506:Sialyl Lewis X Antigen; C107226:tetravalent sialyl Lewis x saccharide; D005643:Fucose; D005647:Fucosyltransferases; D009237:N-Acetyllactosamine Synthase; D012799:Sialyltransferases; D000094663:beta-Galactoside alpha-2,3-Sialyltransferase