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Synthesis of a heparan sulfate tetrasaccharide using automated glycan assembly.

Imlirenla PongenerEric T SlettenJosé Danglad-FloresPeter H SeebergerGavin J Miller
Published in: Organic & biomolecular chemistry (2024)
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.
Keyphrases
  • machine learning
  • deep learning
  • high throughput
  • kidney transplantation
  • sensitive detection