Adaptable synthesis of C-lactosyl glycoclusters and their binding properties with galectin-3.

We report here the syntheses of mono- to tetravalent glycoclusters containing 1-methylene-C-ß-lactose. The 1-methylene-C-ß-lactose moiety has been synthesized from octa-acetyl-ß-lactose using the key carbonyl insertion reaction and linked to a series of alkynlated scaffolds via CuAAC reaction to afford mono- to tetravalent glycoclusters. The binding affinities of the final products to galectin-3 were found in the range of 10-100 µM.