Synthesis of heparan sulfate tetrasaccharide as a substrate for human heparanase

Regiospecifically sulfated heparan sulfate tetrasaccharide, GlcAβ-GlcN(NS6S)α-GlcAβ-GlcN(NS6S)α was first synthesized as an octyl glycoside. Total synthesis was achieved effectively by coupling the corresponding disaccharide units in short steps.

Regiospecifically sulfated heparan sulfate tetrasaccharide, GlcAβ-GlcN(NS6S)α-GlcAβ-GlcN(NS6S)α was first synthesized as an octyl glycoside. Total synthesis was achieved effectively by coupling the corresponding disaccharide units in short steps.Figure optionsDownload as PowerPoint slideHighlight
► Heparan sulfate tetrasaccharides have been synthesized.
► Glycan elongation is available in a stereocontrolled manner.
► Regiospecific N- and O-sulfation of the tetrasaccharide were achieved.
► Unexpected O-sulfation in an aqueous condition was completely suppressed.