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Synthesis of Glycidol- and Sugar-Derived Bicyclic β- and γ/δ-Amino Acids for Peptidomimetic Design
Constrained bicyclic β- and γ/δ-amino acids using glycidol and sugar derivatives were developed. The synthetic strategies involved epoxide ring opening of a glycidol derivative, and subsequent coupling with sugar-derived amines, leading to di- or trisubstitued bicyclic scaffolds after cyclisation with trifluoroacetic acid. Achievement of β- or γ/δ-amino acids was accomplished by changing the protecting group strategy of the starting materials. Compatibility of the scaffold with solid-phase peptide synthesis was assessed by preparing model peptidomimetics using acid- and base-labile resins, thus giving a new tool for peptidomimetic design.
Keywords: Scaffold / Peptidomimetics / Ring opening / Peptides / Amino acids / Solid-phase synthesis