Tandem tetrahydroisoquinoline-4-carboxylic acid/β-alanine as a new construct able to induce a flexible turn
Articolo
Data di Pubblicazione:
2017
Citazione:
Tandem tetrahydroisoquinoline-4-carboxylic acid/β-alanine as a new construct able to induce a flexible turn / M.L. Gelmi, A. Contini, A. Bonetti, R. Bucci, D. Tessaro, F. Clerici, S. Pellegrino, D. Nava. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 23:45(2017 Aug), pp. 10822-10831.
Abstract:
Tetrahydroisoquinoline-4-carboxylic acid, a constrained β2-amino acid named β-TIC, was for the first time synthesized in enantiopure form. The biocatalytic route here applied represents one of the few successful examples of enzymatic resolution of β2-amino acids. Model tetrapeptides, i.e. Fmoc-L-Ala-β-TIC-β-Ala-L-Val-OBn, containing both isomers of β-TIC, were prepared. Both computational and NMR studies were performed. A reverse-turn conformation was observed in the case of R-β-TIC enantiomer, the enantiomer obtained in 99% e.e. by enzymatic resolution. β-TIC/β-Ala construct represents the first example of a flexible turn mimetic containing a cyclic and an acyclic β-amino acid. Furthermore, the presence of an aromatic ring of β-TIC could facilitate non-covalent interactions increasing the potential of this scaffold for the preparation of protein-protein interaction modulators.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
tetrahydroisoquinoline-4-carboxylic acid; beta-amino acid; enzymatic resolution; peptide; turn inducer
Elenco autori:
M.L. Gelmi, A. Contini, A. Bonetti, R. Bucci, D. Tessaro, F. Clerici, S. Pellegrino, D. Nava
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