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

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.

Sensitive and specific enzyme immunoassays for antigenic trisaccharide from Bacillus anthracis spores.

A straightforward synthesis of an anthrose-containing trisaccharide derived from Bacillus anthracis was achieved. Antibodies raised against this hapten provide a highly sensitive enzyme immunoassay with a detection limit of 8.5 pmol mL(-1).

Synthesis of an anthrose derivative and production of polyclonal antibodies for the detection of anthrax spores.

A straightforward synthesis of a derivative of anthrose, the non-reducing terminal fragment of the antigenic tetrasaccharide from Bacillus anthracis, was achieved starting from d-galactose. This hapten is able to induce a highly specific and sensitive immune response in rabbit when attached to a carrier protein.