A new, improved synthesis of the trisaccharide repeating unit of the O-antigen from Xanthomonas campestris pv. campestris 8004

  • Comegna D
  • Bedini E
  • Parrilli M
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Abstract

Recent studies have revealed that lipid-A and core fragments of the lipopolysaccharide from Xanthomonas campestris pv. campestris 8004 (Xcc), a phytopathogenic Gram-negative bacterium, are able to elicit plant immunity with two independent mechanisms. To date, nothing is known about the effect of the O-antigen portion. Since its separation from the core region by selective chemical degradation is very difficult, the chemical synthesis of related oligosaccharides is strictly necessary. In this paper a new, improved synthesis of the O-antigen repeating unit is presented. The main improvements in the synthesis are: (1) a shorter, high-yielding preparation of an efficient glycosyl donor of the rare sugar 3-acetamido-3,6-dideoxy-d-galactopyranose (3-acetamido-d-fucose, d-Fucp3NAc); (2) a new protecting group pattern, which is demonstrated to open a path to the future synthesis of higher oligomers. © 2008 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • 3-Acetamido-d-fucose
  • Glycosylation
  • Xanthomonas
  • d-Rhamnose

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