Solid-Phase Synthesis of Gly-Ψ[CH(CF₃)NH]-Peptides

Abstract

The solid-phase synthesis of Gly-Ψ[CH(CF 3 )NH]-peptides is presented. In order to achieve this goal, the synthesis of Gly-Ψ[CH(CF 3 )NH]-dipeptides having the C-terminus unprotected, the N-terminus protected as Fmoc- or Teoc-, and possibly side chain functionalities protected with acid-labile protecting groups has been developed. A selected small library of six peptidomimetics, encompassing analogues of biological relevant peptides, have been obtained in high purity.

Pull‐Pull Alkenes in the Aza‐Michael Reaction

“…A series of research devoted to the stereoselective aza‐Michael addition of chiral α‐amino acid esters to β‐fluoroalkylnitroalkenes was carried out by Prof. Volonterio's scientific team [106–111] . It was shown that the ( E )‐3,3,3‐trifluoro‐1‐nitropropene 115 a is a good starting material for the synthesis of Gly‐Ψ[CH(R F )NH] peptides.…”

“…A series of research devoted to the stereoselective aza-Michael addition of chiral α-amino acid esters to β-fluoroalkylnitroalkenes was carried out by Prof. Volonterio's scientific team. [106][107][108][109][110][111] It was shown that the (E)-3,3,3-trifluoro-1-nitropropene 115 a is a good starting material for the synthesis of Gly-Ψ[CH-(R F )NH] peptides. The addition of α-amino esters, generated in situ from the corresponding hydrochloride salts 120 in the presence of a base, proceeded in the expected way: the nucleophilic attack was directed on the carbon bearing CF 3 moiety (Scheme 47).…”