APIS group

Amino acids, Peptidomimetics, peptides, protein InteractionS group

unnatural amino acid

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 / unnatural amino acid

Tandem Tetrahydroisoquinoline-4-carboxylic Acid/beta-Alanineasa New Construct Able To Induce a Flexible Turn

Tetrahydroisoquinoline-4-carboxylic acid, a constrained beta-2-amino acid named beta-TIC, wassy in the sised for the first time in enantiopure form .The biocatalytic route applied herein represents one of the few successful examples of enzymatic resolu...

application / unnatural amino acid

Aqueous self-assembly of short hydrophobic peptides containing norbornene amino acid into supramolecular structures with spherical shape

RSC Adv., 2016,6, 90754-90759 DOI: 10.1039/C6RA17116H formation of supramolecular assembly is reported. The two diastereoisomeric pentapeptides AcAla- NRB-Ala-Aib-AlaNH2 1 and 2 containing the two enantiomers of non-proteinogenic norbornene amino acid (NRB) were synthesized in...

application / unnatural amino acid

Ctr-1 Mets7 motif inspiring new peptide ligands for Cu(I)-catalyzed asymmetric Henry reactions under green conditions

RSC Adv., 2016,6, 71529-71533 DOI: 10.1039/C6RA16255J Taking inspiration from the Ctr-1 Mets7 Cu(I) binding motif, effective hybrid catalysts have been developed for asymmetric Henry condensations under green conditions. The introduction of an unnatural dipeptide...

application / unnatural amino acid

Dipeptide Nanotubes Containing Unnatural Fluorine-Substituted β2,3-Diarylamino Acid and L‑Alanine as Candidates for Biomedical Applications

 The synthesis and the structural characterization of dipeptides composed of unnatural fluorine-substituted β2,3-diarylamino acid and L-alanine are reported. Depending on the stereochemistry of the β amino acid, these dipeptides are able to self-assemble into proteolytic stable nanotubes....