Spiro sugar-isoxazolidine scaffold as useful polyfunctional building block for peptidomimetics design
作者： Mylène Richard , Yves Chapleur , Nadia Pellegrini-Moïse
DOI: 10.1016/J.CARRES.2016.01.005
关键词:
摘要: 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 C-7, with arginine, arginine mimetics guanidylated appendages. Two bicyclic sugar derivatives differing the configuration C-7 chosen as model compounds. The small library peptidomimetics was evaluated toward inhibition VEGF-A165/neuropilin-1 binding. Unexpected cleavage C3-C4 bond isoxazolidine moiety observed during hydrogenolysis opened thus a new way hemiketal structures which could also find interesting applications less constrained scaffold.
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