Synthesis of alpha-Gal C-disaccharides

Bioorg Med Chem. 2024 Oct 1:112:117903. doi: 10.1016/j.bmc.2024.117903. Epub 2024 Aug 31.

Abstract

The synthesis of C-disaccharides of α-d-galactopyranosyl-(1 → 3)-d-galactopyranose (α-Gal), potential tools for studying the biology of α-Gal glycans, is described. The synthetic strategy, centers on the reaction of two easily available precursors 1,2-O-isopropylidene-d-glyceraldehyde and an α-C-glactosyl-E-crotylboronate, which affords a mixture of two diastereomeric anti-crotylation products. The stereoselectivity of this reaction was controlled with (R)- and (S)-TRIP catalysts, and the appropriate diastereomer was transformed to C-linked disaccharides of α-Gal, in which the aglycone segment comprised O-, C- and S-glycoside entities that can enable glycoconjugate synthesis.

Keywords: Alpha-Gal; Boronate; C-glycoside; Crotylation; Glycomimetic.

MeSH terms

  • Disaccharides* / chemical synthesis
  • Disaccharides* / chemistry
  • Galactose / chemical synthesis
  • Galactose / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Disaccharides
  • Galactose