Abstract: Herein we utilize 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 Regio specific on-resin 6-O-sulfation. This methodology provides an important benchmark for the rapid assembly of biologically relevant heparan sulfate sequences. AUTHORS: Imlirenla Pongener, Eric T. Sletten, José Danglad-Flores, Peter H. Seeberger and Gavin J. Miller
PUBLICATION DOI: 10.1039/d3ob01909h