Gly-Peptides: Synthesis and Conformation Analysis (Articolo in rivista)

Type
Label
  • Gly-Peptides: Synthesis and Conformation Analysis (Articolo in rivista) (literal)
Anno
  • 2009-01-01T00:00:00+01:00 (literal)
Alternative label
  • Molteni M., Bellucci M.C., Bigotti S., Mazzini S., Volonterio A., Zanda M. (2009)
    Gly-Peptides: Synthesis and Conformation Analysis
    in Organic & biomolecular chemistry
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Molteni M., Bellucci M.C., Bigotti S., Mazzini S., Volonterio A., Zanda M. (literal)
Pagina inizio
  • 2286 (literal)
Pagina fine
  • 2296 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 7 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Marco Molteni,a Maria Cristina Bellucci,b Serena Bigotti,a Stefania Mazzini,b Alessandro Volonterio*a and Matteo Zanda*c,d aDipartimento di Chimica,Materiali, e Ingegneria Chimica \"Giulio Natta\", Politecnico di Milano, via Mancinelli 7, 20131, Milano, Italy. E-mail: alessandro.volonterio@polimi.it; Fax: +39-02-23993080; Tel: +39-02- 23993139 bDipartimento di Scienze Molecolari Agroalimentari, Universit`a degli Studi di Milano, via Celoria 2, 20133, Milano, Italy cC.N.R.-Istituto di Chimica delRiconoscimento Molecolare, Sezione \"Adolfo Quilico\", via Mancinelli 7, 20131, Milano, Italy. E-mail: matteo.zanda@ polimi.it; Fax: +39-02-23993080; Tel: +39-02-23993084 dInstitute of Medical Sciences, University of Aberdeen, Foresterhill, Aberdeen, AB25 2ZD, Scotland, (UK) (literal)
Titolo
  • Gly-Peptides: Synthesis and Conformation Analysis (literal)
Abstract
  • Psi[CH(CF3)NH]Gly peptides, a conceptually new class of peptidomimetics having a stereogenic trifluoroethylamine group as a natural peptide-bond surrogate, have been synthesized by stereoselective addition of alpha-amino acid esters to trans-3,3,3-trifluoro-1-nitropropene. Long range nuclear Overhauser effects, detected via ROESY experiments, provided evidence that model Psi[CH(CF3)NH]Glytetrapeptides incorporating a trifluoroethylamine mimic of the dipeptide loop Pro-Gly can be represented by an ensemble of unfolded and folded conformations. The latter are driven by the formation of a hydrogen bond between a carbonyl group and the aminic proton of the trifluoroethylamine unit. MD calculations indicate a population of conformers which adopt folded beta turn structures for all the L-peptides; on the other hand, a D-stereochemistry at the Pro residue induces a natural folding towards a beta hairpin conformation driven by the formation of a second hydrogen bond, regardless of the stereochemistry of the stereogenic peptide bond surrogate. (literal)
Prodotto di
Autore CNR

Incoming links:


Autore CNR di
Prodotto
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi
data.CNR.it