Abstract

Analysis of glycolipids having repeating core-structures of type 2 chains ([Galβ1→4GlcNAcβ1→3] n Galβ1→4Glcβ1→1Cer) by 1- and 2-dimensional high resolution 1H-n.m.r. spectroscopy shows that fucosylation α1→3 to GlcNAc with or without fucosylation α1→2 to Gal produces predictable chemical shifts of anomeric protons and systematic, glycosylation-induced shift changes. These effects were analyzed for a series of glycolipids of known structure bearing mono- and multimeric X [Galβ1→4(Fucα1→3)GlcNAcβ1→3] and Y [Fucα1→2Galβ1→4(Fucα1→3)GlcNAcβ1→3] determinants, and were subsequently used to elucidate the primary saccharide structure of two novel glycolipids isolated from human liver adenocarcinoma. They are proposed to be Y determinants carried on a norhexaosylceramide core, with the following structures: Fucα1→2Galβ1→4GlcNAcβ1→3Galβ1→4GlcNAcβ1→3Galβ1→4Glcβ1→1Cer ▪

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