Enzyme-assisted synthesis of Asn-linked diantennary oligosaccharides occurring on glycodelin A.
The preparation of a series of sialylated and fucosylated N,N'-diacetyllactosediamine-type diantennary glycopeptides is reported. By sequential enzymatic action of jack bean beta-galactosidase, snail beta 4-N-acetyl-galactosaminyltransferase, bovine colostrum alpha 6-sialyltransferase and human milk alpha 3-fucosyltransferase, a diantennary glycopeptide obtained from asialo fibrinogen was converted at a 5-mumol scale to a series of structures occurring on the glycoprotein glycodelin A, which potentially inhibit human sperm-egg binding.
Hokke
C H
CH
Department of Medical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands.
van den Eijnden
D H
DH
D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002417:Cattle; D007887:Fabaceae / Q000201:enzymology; D005340:Fibrinogen / Q000737:chemistry; D000071816:Glycodelin; D006020:Glycopeptides / Q000138:chemical synthesis*; D006023:Glycoproteins / Q000737:chemistry*; D016695:Glycosyltransferases / Q000378:metabolism; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D010946:Plants, Medicinal; D011257:Pregnancy Proteins / Q000737:chemistry*; D012799:Sialyltransferases / Q000378:metabolism; D012908:Snails / Q000201:enzymology; D001616:beta-Galactosidase / Q000378:metabolism
D000071816:Glycodelin; D006020:Glycopeptides; D006023:Glycoproteins; C045246:PAEP protein, human; D011257:Pregnancy Proteins; D005340:Fibrinogen; D016695:Glycosyltransferases; D012799:Sialyltransferases; D001616:beta-Galactosidase