Abstract
Abstract The α-amino group of ( l )phenylalanine methyl ester was trifluoroethylated using (2,2,2-trifluoroethyl)phenyliodonium N,N-bis(trifluoromethylsulfonyl)imide. A dipeptide Gly( l )Phe containing a trifluoroethylated peptide bond was synthesized by removing the α-amino proton of Nα-trifluoroethyl ( l )phenylalanine methyl ester followed by coupling with Nα-phthaloyl glycine acid fluoride. The dipeptide was further coupled with ( l )leucine methyl ester under conventional carboxyl activation conditions to provide two diastereomers of the tripeptide Gly( d , l )Phe( l )Leu. The solution dynamic behavior of the tripeptide was investigated as a function of solvents, by NOESY and variable temperature (VT) 19F NMR experiments.
Published Version
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