FIFTY FIVE STEP SYNTHESIS OF DEFINED 12-MER FRAGMENTS OF HEPARAN SULFATE

摘要

Heparan sulfates (HSs), highly sulfated glycosaminoglycans, have emerged as a novel and exciting class of molecules with a huge variety of critical functions in cell signalling and development. HSs are made up of repeating 1-4 linked disaccharide units. These are composed of a hexuronic acid and an N-acetyl or N-sulfoglucosamine which bear one or several O-sulfo substituents. Here we report the synthesis of defined dodeca-saccharide fragments of HS in our novel flexible assembly strategy. Glycosylation of orthogonally protected building blocks allowed selective chain elongation at the reducing and non-reducing ends of the molecules to furnish defined fragments of HS (gluco- and ido-configured).