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; A. Volonterio

doi:10.1039/C7OB02680C

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

M. C. Bellucci,^a M. Frigerio,^b C. Castellano,^c F. Meneghetti,^d A. Sacchetti*^b and A. Volonterio*^b

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* Corresponding authors

^a Department of Food, Environmental and Nutritional Sciences, Università degli Studi di Milano, via Celoria 2, 20133 Milano, Italy

^b Department of Chemistry, Materials, and Chemical Engineering “Giulio Natta”, Politecnico di Milano, via Mancinelli 7, 20131 Milano, Italy
E-mail: alessandro.sacchetti@polimi.it, alessandro.volonterio@polimi.it

^c Department of Chemistry, Università degli Studi di Milano, via Golgi 19, 20133 Milano, Italy

^d Department of Pharmaceutical Sciences, Università degli Studi di Milano, via Mangiagalli 25, 20133 Milano, Italy

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.

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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., 2018,16, 521-525

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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, 16, 521
DOI: 10.1039/C7OB02680C
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Organic & Biomolecular Chemistry

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

Abstract

Supplementary files

Publication details

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

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