Categoria: unnatural amino acid

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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....

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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...

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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,...

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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...

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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...

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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...