Conformationally Constrained Mono-Fluorinated Arginine as a Cationic Label for Solid-State 19F NMR Analysis of Membrane-Bound Peptide

Eur. J. Org. Chem. 2018, 27-28, 3826-3833

DOI: 10.1002/ejoc.201800473

Michurin O.; Tolmachova K.; Afonin S.; Babii O.; Grage S.; Ulrich A.; Komarov I.; Radchenko D.

A conformationally constrained mono‐fluorinated analogue of arginine, (1S,3S)‐1‐amino‐3‐fluoro‐3‐(guanidinomethyl)cyclobutane‐1‐carboxylic acid (F‐CbArg), has been designed as a label for solid‐state 19F NMR spectroscopy. The compound was synthesized and its structural and functional similarity to arginine demonstrated in the context of a representative antimicrobial peptide. The cationic 19F NMR label was incorporated into the amphiphilic helix of temporin A and provided information on water and phosphate contacts within the lipid environment, thereby demonstrating the utility of F‐CbArg in structural studies of membrane‐bound peptides.

The application of anthraquinone-based triazenes as equivalents of diazonium salts in reaction with methylene active compounds


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