Background: The biological significance of glycoconjugates has stimulated much synthetic
activity in oligosaccharide synthesis, the sulfate group in sulfated oligosaccharides has been shown to be
constitutively involved in the interaction of ligands with selectins, establishing combinatorial methods for
the synthesis of sulfated oligosaccharide library may be useful for screening of ligands of selectins.
Results: Random sulfation of a partial benzyl protected Lewis A trisaccharide in pyridine provided a
sulfated trisaccharide mixture. After hydrogenation with Pd/C and purification on Sephadex A-50 column,
a monosulfated trisaccharide library was obtained as a mixture. The H-H COSY NMR spectrum
of this mixture showed that this mixture contains all five possible monosulfated Lewis A trisaccharides
with acceptable ratio.
Conclusion: Random sulfation of a partial protected oligosaccharide was demonstrated as the most efficient
method so far for the synthesis of monosulfated oligosaccharide library.