title: Beta-turn induction by C60-based fulleroproline: synthesis and conformational characterization of Fpr/Pro small peptides.
abstract: We have recently described the preparation of Fpr (C60-based fulleroproline). In this paper the synthesis and a conformational characterization of heterochiral di- and tripeptides containing this new alpha-amino acid are reported. A folded structure, induced by the -L-Fpr-D-Ala-sequence in chloroform solution and detected by Fourier transform infrared absorption and 1H nuclear magnetic resonance, has been compared with the known propensity of the cognate -L-Pro-D-Ala-sequence to adopt a beta II-turn conformation, which has also been confirmed in this work. The beta II-turn structure is retained in the crystal state by the Pro-peptides, as shown by the X-ray diffraction structures of Ibu-L-Pro-D-Ala-NHtBu and Z-L-Pro-D-Ala-L-Ala-OtBu.
authors.affiliation: Centro di Studio sui Biopolimeri, Università di Padova, Italy.
authors.forename: A
authors.initials: A
authors.lastname: Bianco
authors.forename: T
authors.initials: T
authors.lastname: Bertolini
authors.forename: M
authors.initials: M
authors.lastname: Crisma
authors.forename: G
authors.initials: G
authors.lastname: Valle
authors.forename: C
authors.initials: C
authors.lastname: Toniolo
authors.forename: M
authors.initials: M
authors.lastname: Maggini
authors.forename: G
authors.initials: G
authors.lastname: Scorrano
authors.forename: M
authors.initials: M
authors.lastname: Prato
mesh_terms: D001426:Bacterial Proteins; D002244:Carbon / Q000737:chemistry*; D002352:Carrier Proteins / Q000737:chemistry*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D037741:Fullerenes; D047908:Intracellular Signaling Peptides and Proteins; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D011487:Protein Conformation; D017433:Protein Structure, Secondary; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D001426:Bacterial Proteins; D002352:Carrier Proteins; D037741:Fullerenes; D047908:Intracellular Signaling Peptides and Proteins; D010455:Peptides; C028640:fructose-induced HPr-like protein, bacteria; D002244:Carbon; D011392:Proline; C069837:fullerene C60