Spectroscopically Labeled Peptaibiotics. Synthesis and Properties of Selected Trichogin GA IV Analogs Bearing a Side-Chain-Monofluorinated Aromatic Amino Acid for 19F-NMR Analysis (Articolo in rivista)

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

Label

• Spectroscopically Labeled Peptaibiotics. Synthesis and Properties of Selected Trichogin GA IV Analogs Bearing a Side-Chain-Monofluorinated Aromatic Amino Acid for 19F-NMR Analysis (Articolo in rivista) (literal)

Anno

• 2013-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1002/cbdv.201200389 (literal)

Alternative label

• C. Peggion, B. Biondi, M. De Zotti, S. Oancea, F. Formaggio, C. Toniolo (2013)
  Spectroscopically Labeled Peptaibiotics. Synthesis and Properties of Selected Trichogin GA IV Analogs Bearing a Side-Chain-Monofluorinated Aromatic Amino Acid for 19F-NMR Analysis
  in Chemistry & biodiversity (Online)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• C. Peggion, B. Biondi, M. De Zotti, S. Oancea, F. Formaggio, C. Toniolo (literal)

Pagina inizio

• 904 (literal)

Pagina fine

• 919 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 10 (literal)

Rivista

• Chemistry & biodiversity (Rivista)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• ICB, Padova Unit, CNR, Department of Chemistry, University of Padova, 35131 Padova, Italy; Department of Biochemistry ad Toxicology, Lucian Blaga University of Sibiu, 550012 Sibiu, Romania (literal)

Titolo

• Spectroscopically Labeled Peptaibiotics. Synthesis and Properties of Selected Trichogin GA IV Analogs Bearing a Side-Chain-Monofluorinated Aromatic Amino Acid for 19F-NMR Analysis (literal)

Abstract

• We prepared by solid-phase methods, chromatographically purified, and characterized three analogs of the ten-amino acid-residue, membrane-active, lipopeptaibiotic trichogin GA IV, each containing a single (4-fluorophenyl)alanine in position 3, 7, or 10, where it replaces the hydrophobic residue Leu3, Leu7, or Ile10, respectively. We incorporated the fluorine probe based on the observation that the 19F-NMR technique has been extensively utilized to analyze peptidemembrane interactions in biological systems. A detailed conformational investigation in solution, including a membrane-mimetic environment, was performed on these compounds using FT-IR absorption, CD, and 2D-NMR, combined with molecular-dynamics calculations. The experimentally observed, mixed 310/-helical structures unequivocally show that the principal conformational features of trichogin GA IV are preserved in all three analogs. Analogies and differences between the behavior of the natural lipopeptaibiotic and those of the peptides characterized by the side-chain monofluorinated aromatic amino acid were found in membrane-permeabilization experiments and antimicrobial assays. The results of a preliminary solution 19F-NMR study support the view that the 19F label is an excellent reporter for changes in the helical environment of the peptide. (literal)

Prodotto di

• Peptidi da amminoacidi non proteici con potenzialità in nanomedicina (PM.P01.021.001) (Modulo)
• Istituto di chimica biomolecolare (ICB) (Istituto)

Autore CNR

• BARBARA BIONDI (Unità di personale interno)
• CLAUDIO TONIOLO (Persona)
• FERNANDO FORMAGGIO (Unità di personale esterno)

Insieme di parole chiave

• Keywords of "Spectroscopically Labeled Peptaibiotics. Synthesis and Properties of Selected Trichogin GA IV Analogs Bearing a Side-Chain-Monofluorinated Aromatic Amino Acid for 19F-NMR Analysis" (Insieme di parole chiave)

Incoming links:

Autore CNR di

• BARBARA BIONDI (Unità di personale interno)
• CLAUDIO TONIOLO (Persona)
• FERNANDO FORMAGGIO (Unità di personale esterno)

Prodotto

• Istituto di chimica biomolecolare (ICB) (Istituto)
• Peptidi da amminoacidi non proteici con potenzialità in nanomedicina (PM.P01.021.001) (Modulo)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Chemistry & biodiversity (Rivista)

Insieme di parole chiave di

• Keywords of "Spectroscopically Labeled Peptaibiotics. Synthesis and Properties of Selected Trichogin GA IV Analogs Bearing a Side-Chain-Monofluorinated Aromatic Amino Acid for 19F-NMR Analysis" (Insieme di parole chiave)