Kinetics of photochemical isomerization of TFA-Gly-ZΔPhe into TFA-Gly-EΔPhe

Abstract

The kinetics of photoisomerization of trifluoroacetyl-(Z)-dehydrophenylalanylglycine into trifluoroacetyl-(E)-dehydrophenylalanylglycine was studied in the hope that light-induced reaction could be useful as a means of preparation of the E-dehydropeptides. The obtained results indicate that if this reaction carried out under irradiation with light of wavelength 360 nm it is practically irreversible and gave nearly quantitatively pure Eisomer Significantly, expected cyclic side-products were not observed in the reaction mixture, thus proving the preparative potential of the elaborated procedure.

Insight into the Structure of Victorin, the Host-Selective Toxin from the Oat PathogenCochliobolus victoriae. Studies of the Unique Dehydroamino Acid β-Chlorodehydroalanine

“…To complete the preparation of β-chlorodehydroalanine model structures, the isomerization from the isomers Z into E assisted by UV irradiation was performed. The photoisomerization Z / E of simple dehydroamino acid residues is known. , However, according to the best of our knowledge, the application of this reaction to the β-halogenodehydroalanyl residue is reported for the first time here. The optimal reaction conditions in this case include the irradiation of the reaction mixture with UV light with a maximum wavelength of 366 nm at 5 h with an intensity of 400–440 μW/cm 2 (Figure d).…”