APIS group

Amino acids, Peptidomimetics, peptides, protein InteractionS group

application

application / unnatural amino acid

Stereoselective Synthesis of α,α′-Dihydroxy-beta, beta′-diaryl-beta-amino Acids by Mannich-Like Condensation of Hydroarylamides

Dual α,α′-Dihydroxy-beta,beta’-beta-amino acids are highly interesting tools for several industrial applications. Nevertheless, only few derivatives are reported in the literature and knowledge concerning the substitution pattern as well as their enantioselective syntheses are lacking....

application

On‑resin multicomponent 1,3‑dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides as an efficient tool for the synthesis of amidino depsipeptide mimics

Depsipeptides are biologically active peptide derivatives that possess a high therapeutic interest. The development of depsipeptide mimics characterized by a chemical diversity could lead to compounds with enhanced features and activity. In this work,...

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...

application / Peptidomimetics

Tetrahydro‑4H‑(pyrrolo[3,4‑d]isoxazol-3-yl)methanamine: A Bicyclic Diamino Scaffold Stabilizing Parallel Turn Conformations

A tetrahydro-4H-(pyrrolo[3,4-d]isoxazol-3-yl)methanamine
scaffold was designed as a diamino derivative to stabilize parallel turn
conformations. Its synthesis took advantage of a [1,3]-dipolar cycloaddition
reaction between the nitrile oxide derived from the inexpensive enantiopure Lphenylalanine
and N-benzyl-3-pyrroline. Two diastereoisomers were formed,
whose distribution depends on the selected base. 3aR,6aS-Isomer is favored in
organic bases, which formation is driven by π-interactions. However, the above
interactions were significantly prevented using an inorganic base due to the
chaotropic effect of the cation, decreasing the amount of the above isomer.
Finally, we demonstrated that this isomer is able to stabilize parallel turn
conformations when inserted in short peptide sequences.