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Synthesis of an STnThr analogue, structurally based on a TnThr antigen mimetic
Francesco Papi1, Arnaud Pâris2, Pierre Lafite2
1Department of Chemistry, University of Florence, via della Lastruccia, 3-13, I-50119 Sesto F.no (FI), Italy. cristina.nativi@unifi.it.
Abstract:
The monosaccharide Tn and the disaccharide STn are tumor antigens with similar structures and common biosynthetic pathways. Both are always over-expressed simultaneously on tumor cell surfaces. We report herein the efficient synthesis of the STnThr antigen analogue 2, featuring the immunogenic TnThr mimetic 1 aglycon. Analogously to the native STn, 2 is recognized by the influenza N1 neuraminidase. A model of the N1·2 complex showed the sialyl moiety of 2 well nested in the active site pocket, with docking unaffected by the rigid aglycon. The analogue 2 is, therefore, in association with mimetic 1, a good determinant for the design of new multiantigen cancer vaccines.
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