Synthesis of n-octyl 2,6-dideoxy-alpha-L-lyxo-hexopyranosyl-(1-->2)-3-amino-3-deoxy-beta-D-galactopyranoside, an analog of the H-disaccharide antigen

Carbohydr Res. 2006 Jul 24;341(10):1702-7. doi: 10.1016/j.carres.2006.03.018. Epub 2006 Apr 17.

Abstract

The synthesis of an analog of the H-disaccharide antigen (2), in which the galactopyranosyl moiety bears an amino group at C-3 and the fucopyranosyl residue is deoxygenated at C-2, is reported. The key reaction in the preparation of 2 was the glycosylation of an appropriately protected n-octyl 3-azido-3-deoxy-galactopyranoside derivative with a 2,6-dideoxy thioglycoside promoted by 1-(phenylsulfinyl)piperidine and triflic anhydride. Disaccharide 2 is of interest in studies directed towards understanding the molecular basis of substrate recognition by the blood group A and B glycosyltransferases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antigens, Bacterial / chemistry*
  • Carbohydrate Sequence
  • Disaccharides / chemical synthesis*

Substances

  • Antigens, Bacterial
  • Disaccharides
  • H antigen