Twelve trisaccharide derivatives designed for detailed exploration of
the acceptor specificity of sialyltransferases involved in the biosynt
hesis of N-glycans have been synthesized. These compounds include beta
-o-GlcpNAc-(1-2)-alpha-D-Manp-(1-0)(CH2)(7)CH3 and analogues containin
g structural variants of D-galactose. All trisaccharides were obtained
by condensation of suitably modified glycosyl donors with a single di
saccharide acceptor, thus limitating the number of reaction steps requ
ired. After deprotection, the compounds were employed to delineate the
recognition characteristics of several natural and recombinant sialyl
transferases.