title: Design, Synthesis, and Application of an Optimized Monofluorinated Aliphatic Label for Peptide Studies by Solid-State19F NMR Spectroscopy.
abstract: A conformationally restricted monofluorinated α-amino acid, (3-fluorobicyclo[1.1.1]pentyl)glycine (F-Bpg), was designed as a label for the structural analysis of membrane-bound peptides by solid-state19F NMR spectroscopy. The compound was synthesized and validated as a19F label for replacing natural aliphatic α-amino acids. Calculations suggested that F-Bpg is similar to Leu/Ile in terms of size and lipophilicity. The19F NMR label was incorporated into the membrane-active antimicrobial peptide PGLa and provided information on the structure of the peptide in a lipid bilayer.
authors.affiliation: Enamine Ltd, Chervonotkatska 78, 02094, Kyiv, Ukraine.|Institute of High Technologies, Taras Shevchenko National University of Kyiv, Volodymyrska 60, 01601, Kyiv, Ukraine.
authors.forename: Serhii O
authors.initials: SO
authors.lastname: Kokhan
authors.affiliation: Enamine Ltd, Chervonotkatska 78, 02094, Kyiv, Ukraine.|Institute of High Technologies, Taras Shevchenko National University of Kyiv, Volodymyrska 60, 01601, Kyiv, Ukraine.
authors.forename: Andriy V
authors.initials: AV
authors.lastname: Tymtsunik
authors.affiliation: Institute of Biological Interfaces (IBG-2), Karlsruhe Institute of Technology (KIT), POB 3640, 76021, Karlsruhe, Germany.
authors.forename: Stephan L
authors.initials: SL
authors.lastname: Grage
authors.affiliation: Institute of Biological Interfaces (IBG-2), Karlsruhe Institute of Technology (KIT), POB 3640, 76021, Karlsruhe, Germany.
authors.forename: Sergii
authors.initials: S
authors.lastname: Afonin
authors.affiliation: Institute of Organic Chemistry (IOC), KIT, Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Oleg
authors.initials: O
authors.lastname: Babii
authors.affiliation: Institute of Organic Chemistry (IOC), KIT, Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Marina
authors.initials: M
authors.lastname: Berditsch
authors.affiliation: Enamine Ltd, Chervonotkatska 78, 02094, Kyiv, Ukraine.
authors.forename: Alexander V
authors.initials: AV
authors.lastname: Strizhak
authors.affiliation: Enamine Ltd, Chervonotkatska 78, 02094, Kyiv, Ukraine.
authors.forename: Dmytro
authors.initials: D
authors.lastname: Bandak
authors.affiliation: Enamine Ltd, Chervonotkatska 78, 02094, Kyiv, Ukraine.
authors.forename: Maxim O
authors.initials: MO
authors.lastname: Platonov
authors.affiliation: Institute of High Technologies, Taras Shevchenko National University of Kyiv, Volodymyrska 60, 01601, Kyiv, Ukraine.
authors.forename: Igor V
authors.identifier: 0000-0002-7908-9145
authors.initials: IV
authors.lastname: Komarov
authors.affiliation: Institute of Biological Interfaces (IBG-2), Karlsruhe Institute of Technology (KIT), POB 3640, 76021, Karlsruhe, Germany.|Institute of Organic Chemistry (IOC), KIT, Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Anne S
authors.initials: AS
authors.lastname: Ulrich
authors.affiliation: Enamine Ltd, Chervonotkatska 78, 02094, Kyiv, Ukraine.|Chemistry Department, Taras Shevchenko National University of Kyiv, Volodymyrska 64, 01601, Kyiv, Ukraine.
authors.forename: Pavel K
authors.initials: PK
authors.lastname: Mykhailiuk
keywords: amino acids; fluorine; peptides; propellanes; solid-state NMR spectroscopy