Skip to Main content Skip to Navigation
Journal articles

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.
Document type :
Journal articles
Complete list of metadatas

https://hal.univ-lorraine.fr/hal-01496653
Contributor : Srsmc Ul <>
Submitted on : Monday, March 27, 2017 - 4:47:45 PM
Last modification on : Thursday, October 1, 2020 - 3:28:02 PM

Identifiers

Collections

Citation

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⟩

Share

Metrics

Record views

120