Issue 37, 2020

Synthesis of an STnThr analogue, structurally based on a TnThr antigen mimetic

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.

Graphical abstract: Synthesis of an STnThr analogue, structurally based on a TnThr antigen mimetic

Supplementary files

Article information

Article type
Paper
Submitted
24 8 2020
Accepted
04 9 2020
First published
07 9 2020

Org. Biomol. Chem., 2020,18, 7366-7372

Synthesis of an STnThr analogue, structurally based on a TnThr antigen mimetic

F. Papi, A. Pâris, P. Lafite, R. Daniellou and C. Nativi, Org. Biomol. Chem., 2020, 18, 7366 DOI: 10.1039/D0OB01749C

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