Synthesis of a heparan sulfate tetrasaccharide using automated glycan assembly.

ABSTRACT: Herein we utilise automated glycan assembly to complete solid-phase synthesis of defined heparan sulfate oligosaccharides, employing challenging D-glucuronate disaccharide donors. Using an orthogonally protected D-GlcN-α-D-GlcA donor, milligram-scale synthesis of a heparan sulfate tetrasaccharide is completed in 18% yield over five steps. Furthermore, orthogonal protecting groups enabled regiospecific on-resin 6-O-sulfation. This methodology provides an important benchmark for the rapid assembly of biologically relevant heparan sulfate sequences.

SUBMITTER: Pongener I 

PROVIDER: S-EPMC10865181 | biostudies-literature | 2024 Feb

REPOSITORIES: biostudies-literature