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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.
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https://hal-univ-orleans.archives-ouvertes.fr/hal-03478288
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Submitted on : Monday, December 13, 2021 - 10:00:54 PM
Last modification on : Sunday, June 26, 2022 - 3:24:57 AM

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Francesco Papi, Arnaud Pâris, Pierre Lafite, Richard Daniellou, Cristina Nativi. Synthesis of an STnThr analogue, structurally based on a TnThr antigen mimetic. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2020, 18 (37), pp.7366-7372. ⟨10.1039/D0OB01749C⟩. ⟨hal-03478288⟩

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