(R)-α-Trifluoromethylalanine as a 19 F NMR Probe for the Monitoring of Protease Digestion of Peptides

Abstract

Fluorinated non-natural amino acids are useful tools for improving the bioavailability of peptides but can also serve as fluorinated probes in ¹⁹ F NMR-based enzymatic assays. We report herein that the use of the non-natural α-quaternarized (R)-α-trifluoromethylalanine ((R)-α-TfmAla) provides convenient and accurate monitoring of trypsin proteolytic activity and increases resistance towards pepsin degradation.

Keywords: FABS; NMR spectroscopy; pepsin; trifluoromethylated peptides; trypsin.