Design,Synthesis, and Application of an Optimized Monofluorinated Aliphatic Label for Peptide Studies by Solid‐State 19F NMR Spectroscopy |
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| Authors: | Serhii O Kokhan Andriy V Tymtsunik Dr Stephan L Grage Dr Sergii Afonin Dr Oleg Babii Dr Marina Berditsch Alexander V Strizhak Dmytro Bandak Dr Maxim O Platonov Prof Igor V Komarov Prof Anne S Ulrich Dr Pavel K Mykhailiuk |
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| Institution: | 1. http://www.enamine.net;2. Enamine Ltd, Kyiv, Ukraine;3. Institute of High Technologies, Taras Shevchenko National University of Kyiv, Kyiv, Ukraine;4. http://www.ibg.kit.edu/nmr;5. Institute of Biological Interfaces (IBG-2), Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany;6. Institute of Organic Chemistry (IOC), KIT, Karlsruhe, Germany;7. Chemistry Department, Taras Shevchenko National University of Kyiv, Kyiv, Ukraine |
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| Abstract: | A conformationally restricted monofluorinated α‐amino acid, (3‐fluorobicyclo1.1.1]pentyl)glycine (F‐Bpg), was designed as a label for the structural analysis of membrane‐bound peptides by solid‐state 19F NMR spectroscopy. The compound was synthesized and validated as a 19F label for replacing natural aliphatic α‐amino acids. Calculations suggested that F‐Bpg is similar to Leu/Ile in terms of size and lipophilicity. The 19F NMR label was incorporated into the membrane‐active antimicrobial peptide PGLa and provided information on the structure of the peptide in a lipid bilayer. |
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| Keywords: | amino acids fluorine peptides propellanes solid-state NMR spectroscopy |
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