title: Synthetic studies toward the anthrax tetrasaccharide: alternative synthesis of this antigen.
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.
authors.affiliation: Laboratoire des Glucides, FRE CNRS 3517, Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens Cedex, France.
authors.forename: Ophélie
authors.initials: O
authors.lastname: Milhomme
authors.forename: Sandrine G Y
authors.initials: SG
authors.lastname: Dhénin
authors.forename: Florence
authors.initials: F
authors.lastname: Djedaïni-Pilard
authors.forename: Vincent
authors.initials: V
authors.lastname: Moreau
authors.forename: Cyrille
authors.initials: C
authors.lastname: Grandjean
mesh_terms: D000081:Acetamides; D000606:Amino Sugars / Q000737:chemistry*; D000818:Animals; D000942:Antigens, Bacterial / Q000737:chemistry* / Q000276:immunology; D001408:Bacillus anthracis / Q000737:chemistry* / Q000276:immunology; D062845:Chloroacetates; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry; D004952:Esters; D005643:Fucose / Q000737:chemistry*; D006031:Glycosylation; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis*; D012210:Rhamnose / Q000737:chemistry*; D014238:Trichloroacetic Acid / Q000737:chemistry
chemical_list: C504007:4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methylglucopyranose; D000081:Acetamides; D000606:Amino Sugars; D000942:Antigens, Bacterial; D062845:Chloroacetates; D004952:Esters; D009844:Oligosaccharides; D005643:Fucose; D014238:Trichloroacetic Acid; D003847:Deoxyglucose; C009528:trichloroacetamide; D012210:Rhamnose