Synthesis and characterization of sulfated Gal-β-1,3/4-GlcNAc disaccharides through consecutive protection/glycosylation steps

Abstract

We have developed an expeditious procedure to yield large amounts of orthogonally protected Gal-β1,3/4-GlcNAc, which allowed for the systematic introduction of a sulfate group onto the C3/C6 positions of Gal and/or the C6 position of GlcNAc. In particular, the disaccharide precursors were prepared in five or six steps and high overall yield from para-tolyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside. After deprotection and sulfation steps, the final products were characterized by using several NMR methods to unambiguously confirm the location of each introduced sulfate group and they were examined for their binding specificity of human galectin-1 and galectin-8.