Protease Catalyzed and Chemical Peptide Bond Formation with α-Trifluoromethyl Substituted α-Amino Acids

Article abstract of DOI:10.1002/prac.19933350404

Subtilisin, α-chymotrypsin and papain catalyzed hydrolyses of α-trifluoromethyl substituted N-benzyloxycarbonyl amino acid methylesters (Z-TFM-Xaa-OMe) 1 can be achieved only in the case of 3,3,3-trifluoroalanine.Enzymatic incorporation of Z-TFM amino acids 2 into N-terminal position of dipeptides also fails.In contrary, dipeptides with a TFM amino acid moiety in N-terminal position, e.g.TFM-Phg-L-Phe-OMe 5, react with H-Leu-NH2 to give the corresponding tripeptides 6 in high yield.Z protected dipeptide derivatives 8 with N-terminal TFM amino acids can be obtained via 4-trifluoromethyl-5-(4H)-oxazolones 7.