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Stereodivergent synthesis of 5-aminopipecolic acids and application in the preparation of a cyclic RGD peptidomimetic as a nanomolar αVβ3 integrin ligand

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Abstract

A stereodivergent strategy was devised to obtain enantiopure cis and trans 5-aminopipecolic acids (5-APAs) in suitably protected forms to be employed in peptide synthesis as conformationally constrained α- and δ-amino acids. The cis isomer was used as a δ-amino acid to construct a cyclic RGD-containing peptidomimetic, the ability of which to compete with biotinylated vitronectin for binding with the isolated αVβ3 integrin was measured (IC50 = 4.2 ± 0.9 nM). A complete 1H NMR and computational conformational analysis was performed to elucidate the reasons for the high affinity of this cyclic peptidomimetic in comparison with cilengitide.

Graphical abstract: Stereodivergent synthesis of 5-aminopipecolic acids and application in the preparation of a cyclic RGD peptidomimetic as a nanomolar αVβ3 integrin ligand

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Publication details

The article was received on 02 Mar 2018, accepted on 11 Apr 2018 and first published on 11 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00534F
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Stereodivergent synthesis of 5-aminopipecolic acids and application in the preparation of a cyclic RGD peptidomimetic as a nanomolar αVβ3 integrin ligand

    L. Sernissi, L. Ricci, D. Scarpi, F. Bianchini, D. Arosio, A. Contini and E. G. Occhiato, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00534F

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