Synthesis of biotinylated chondroitin sulfate DA and AD tetrasaccharides composed of hetero-type disaccharide units, and their interactions with the mAb MO-225.

Chondroitin sulfate (CS), a linear acidic polysaccharide, exhibits numerous biological activities that are dependent on sulfation patterns. CS oligosaccharides comprise repeating disaccharide units with different (hetero)-type sulfation patterns and are common in nature. We herein report the synthesis of the following biotinylated CS tetrasaccharides: CS-AD [βGalNAc4S(1-4)βGlcA(1-3)βGalNAc6S(1-4)βGlcA2S] and CS-DA [βGalNAc6S(1-4)βGlcA2S(1-3)βGalNAc4S(1-4)βGlcA], in a stereo-controlled manner. We also demonstrated that the CS-d-specific monoclonal antibody MO-225 bound more strongly to CS-DA than to CS-DD or -AD.