Chemistry - A European Journal p. 10822 - 10831 (2017)
Update date:2022-08-16
Topics:
Bucci, Raffaella
Bonetti, Andrea
Clerici, Francesca
Contini, Alessandro
Nava, Donatella
Pellegrino, Sara
Tessaro, Davide
Gelmi, Maria Luisa
Tetrahydroisoquinoline-4-carboxylic acid, a constrained β2-amino acid named β-TIC, was synthesised for the first time in enantiopure form. The biocatalytic route applied herein represents one of the few successful examples of enzymatic resolution of β2-amino acids. Model tetrapeptides, namely, Fmoc-l-Ala-β-TIC-β-Ala-l-Val-OBn (Fmoc=fluorenylmethyloxycarbonyl, Bn=benzyl), containing both isomers of β-TIC, were prepared. Both computational and NMR spectroscopy studies were performed. A reverse-turn conformation was observed in the case of (R)-β-TIC enantiomer that was obtained in 99 % enantiomeric excess by enzymatic resolution. The 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 to increase the potential of this scaffold for the preparation of protein–protein interaction modulators.
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