Substrates for the differentiation of the <i>N</i>-acetylglucosaminytransferases. Synthesis of β<scp>D</scp>GlcNAc(1 → 2)α<scp>D</scp>Man(1 → 6)β<scp>D</scp>Man and β<scp>D</scp>GlcNAc(1 → 2)α<scp>D</scp>Man(1 → 6) [α<scp>D</scp>Man(1 → 3)]β<scp>D</scp>Man glycosides

Abstract

The trisaccharide βDGlcNAc(1 → 2)αDMan(1 → 6)βDMan (2) and the tetrasaccharide βDGlcNAc(1 → 2)αDMan(1 → 6)[αDMan(1 → 3)]βDMan (3) have been chemically synthesized as their 8-methoxycarbonyloctyl glycosides. Compounds 2 and 3, both partial structures of naturally occurring asparagine linked oligosaccharides, are designed to function as selective substrates in N-acetylglucosaminytransferase assays.