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

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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.