152604-24-5Relevant articles and documents
Protease Catalyzed and Chemical Peptide Bond Formation with α-Trifluoromethyl Substituted α-Amino Acids
Burger, Klaus,Muetze, Kerstin,Hollweck, Wolfgang,Koksch, Beate,Kuhl, Peter,et al.
, p. 321 - 331 (2007/10/02)
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.