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

Abstract : 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.
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Carbohydrate Research, Elsevier, 2016, 422, pp.24-33. 〈10.1016/j.carres.2016.01.005〉
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https://hal.univ-lorraine.fr/hal-01496653
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Soumis le : lundi 27 mars 2017 - 16:47:45
Dernière modification le : mardi 16 janvier 2018 - 10:24:44

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

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