Design, synthesis, and conformational analysis of 3-cyclo-butylcarbamoyl hydantoins as novel hydrogen bond driven universal peptidomimetics. Issue 4 (6th December 2017)

• Record Type: Journal Article
• Authors: Bellucci, M. C.; Frigerio, M.; Castellano, C.; Meneghetti, F.; Sacchetti, A.; Volonterio, A.
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 4(2017)
• Page Start: 521
• Page End: 525
• Publication Date: 2017-12-06
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob02680c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : 3- cyclo -Butylcarbamoyl hydantoins are able to mimic α-helix and β-turn secondary structures as assessed by molecular modeling, NMR studies, and X-ray analysis. 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.