APIS group

Amino acids, Peptidomimetics, peptides, protein InteractionS group

Peptidomimetics

application / Peptidomimetics

A Non-coded β2,2-Amino Acid with Isoxazoline Core Able to Stabilize Peptides Folding Through an Unprecedented Hydrogen Bond

New peptidomimetics containing a β2,2-isoxazoline amino acid, i.e. 5-(aminomethyl)-3-phenyl-4,5-dihydroisoxazole- 5-carboxylic acid (Isox-β2,2AA), were prepared and studied by NMR and theoretical calculation. Although similar amino acid derivatives have already been prepared via 1,3-dipolar cycloaddition reaction,...

application / News / Peptidomimetics / unnatural amino acid

Nucleobase morpholino β amino acids as molecular chimeras for the preparation of photoluminescent materials from ribonucleosides

Bioinspired smart materials represent a tremendously growing research field and the obtainment of new building blocks is at the molecular basis of this technology progress. In this work, colloidal materials have been prepared in...

application / Peptidomimetics / unnatural amino acid

Non-natural 3‑Arylmorpholino-β-amino Acid as a PPII Helix Inducer

A new non-natural β-amino acid, named 3-Ar-β-Morph, was designed and synthesized via a regio- and diastereoselective Pdcatalyzed C(sp3)H-arylation of the corresponding 2S,6S-(6-methoxymorpholin-2-yl)carboxylic acid, readily available from glucose. According to the computational prevision and confirmed...

application / Peptidomimetics / unnatural amino acid

Bicyclic Pyrrolidine-Isoxazoline γ Amino Acid: A Constrained Scaffold for Stabilizing α-Turn Conformation in Isolated Peptides

amino acids have tremendously expanded the folding possibilities of peptides and peptide mimics. While α,α-disubstituted and β-amino acids are widely studied, γ-derivatives have been less exploited. Here we report the conformational study on the...

application / Peptidomimetics / unnatural amino acid

Fluoro-Aryl Substituted α,β2,3-Peptides in the Development of Foldameric Antiparallel β-Sheets: A Conformational Study

α,β2,3-Disteroisomeric foldamers of general formula Boc(S-Ala-β-2R,3R-Fpg)nOMe or Boc(S-Ala-β-2S,3S-Fpg)nOMe were prepared from both enantiomers of syn H-2-(2-F-Phe)-h-PheGly-OH (named β-Fpg) and S-alanine. Our peptides show two appealing features for biomedical applications: the presence of fluorine, attractive for non-covalent interactions,...

application / Peptidomimetics / unnatural amino acid

From glucose to enantiopure morpholino β-amino acid: a new tool for stabilizing γ-turns in peptide

A new cyclic enantiopure β-amino acid, named β-Morph, containing the morpholino ring, was obtained in gram scale starting from an α-D-glucopyranose enantiopure material, focusing on the “environmental sustainability” concept. A series of ultrashort model...