Spiro sugar-isoxazolidine scaffold as useful polyfunctional building block for peptidomimetics design - Université de Lorraine Accéder directement au contenu
Article Dans Une Revue Carbohydrate Research Année : 2016

Spiro sugar-isoxazolidine scaffold as useful polyfunctional building block for peptidomimetics design

Résumé

Spiro sugar-isoxazolidines obtained by 1,3-dipolar cycloaddition of activated exo-glycals and nitrones were efficiently functionalized at two sites, i.e. C-4 and C-7, with arginine, arginine mimetics and guanidylated appendages. Two bicyclic sugar derivatives differing by the configuration at C-7 were chosen as model compounds. The small library of peptidomimetics was evaluated toward inhibition of VEGF-A165/neuropilin-1 binding. Unexpected cleavage of C3-C4 bond of isoxazolidine moiety was observed during hydrogenolysis and opened thus a new way toward hemiketal structures which could also find interesting applications as less constrained scaffold.

Domaines

Chimie
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Dates et versions

hal-01496653 , version 1 (27-03-2017)

Identifiants

Citer

Mylène Richard, Yves Chapleur, Nadia Pellegrini-Moïse. Spiro sugar-isoxazolidine scaffold as useful polyfunctional building block for peptidomimetics design. Carbohydrate Research, 2016, 422, pp.24-33. ⟨10.1016/j.carres.2016.01.005⟩. ⟨hal-01496653⟩
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