ENZYMATIC GLYCOSPHINGOLIPID SYNTHESIS ON POLYMER SUPPORTS .2. SYNTHESIS OF LACTOSYL CERAMIDE

In a first example of a polymer-supported enzymic synthesis of glycosphingolipids, synthetic (2 S,3 R,4 E)-2-amino-1-(β-d-glucopyranosyloxy)-3-hydroxy-4-octadecene (glucosylsphingosine) was converted to the N-4-carboxymethyl-2-nitrobenzyloxycarbonyl derivative and was subsequently attached to a water-soluble polymer. The material served as an acceptor in the d-galactosyltransferase reaction (36% transfer yield) and further photolysis, acylation and chromatography afforded (2 S,3 R,4 E)-1-[4-O-(β-d-galactopyranosyl)-β-d-glycopyranosyloxy]-3-hydroxy-2-octadecanoylamino-4-octadecene (lactosylceramide, 54% yield). © 1990 Glycoconjugate Journal AB.