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Synthetic studies toward the anthrax tetrasaccharide: alternative synthesis of this antigen

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
356
Identifiers
DOI: 10.1016/j.carres.2012.01.007
Keywords
  • Bacillus Anthracis
  • Anthrose
  • Exosporium Glycoprotein
  • Oligosaccharide
  • Kuhn’S Methylation
Disciplines
  • Chemistry

Abstract

Abstract The synthesis of the anthrax tetrasaccharide, amenable for conjugation, has been envisaged by both [2+2] and [1+3] approaches from d-fucose and l-rhamnose. The successful route reported herein relies on a [1+3] strategy in which the 1,2-trans-glycosidic linkages have been secured using a participating group at the 2-position of the donors using conventional thio as well as trichloroacetimidate glycosylation chemistry. The exchange of the ester to benzyl protective groups on the rhamnosyl moiety was key to achieve the final assembly and functionalization of the tetrasaccharide.

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