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Design, synthesis, and conformational analysis of 3-cyclo-butylcarbamoyl hydantoins as novel hydrogen bond driven universal peptidomimetics

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Abstract

A collection of systematically substituted 3-cyclo-butylcarbamoyl hydantoins was synthesized by a regioselective multicomponent domino process followed by easy coupling reactions. Calculations, NMR studies and X-ray analysis show that these scaffolds are able to project their side chains similar to common secondary structures, such as the α-helix and β-turn, with favourable enthalpic and entropic profiles.

Graphical abstract: Design, synthesis, and conformational analysis of 3-cyclo-butylcarbamoyl hydantoins as novel hydrogen bond driven universal peptidomimetics

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Publication details

The article was received on 31 Oct 2017, accepted on 27 Nov 2017 and first published on 27 Nov 2017


Article type: Communication
DOI: 10.1039/C7OB02680C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Design, synthesis, and conformational analysis of 3-cyclo-butylcarbamoyl hydantoins as novel hydrogen bond driven universal peptidomimetics

    M. C. Bellucci, M. Frigerio, C. Castellano, F. Meneghetti, A. Sacchetti and A. Volonterio, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02680C

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