Synthesis of a water-soluble serine-based neoglycolipid which can be covalently linked to solid phases.
N alpha-Fmoc-serine pentafluorophenyl ester was glycosylated with perbenzoylated lactosyl bromide. The resulting product was coupled to a resin functionalized with 6-aminohexanoic acid and then N alpha-acylated to give a serine-based analogue of lactosylceramide. The water-soluble neoglycolipid was covalently linked to microtiter plates via its carboxyl group and was recognized by a lactose-binding lectin in an ELISA.
Elofsson
M
M
Chemical Center, University of Lund, Sweden.
Broddefalk
J
J
Ekberg
T
T
Kihlberg
J
J
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004797:Enzyme-Linked Immunosorbent Assay; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D007202:Indicators and Reagents; D007790:Lactosylceramides / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009904:Optical Rotation; D012694:Serine
D006001:Glycoconjugates; D006017:Glycolipids; D007202:Indicators and Reagents; D007790:Lactosylceramides; D012694:Serine