Synthesis and photochemical reactivity of phthalimidoadamantane-tyrosine conjugates (CROSBI ID 236982)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Sohora, Margareta; Vidović, Nikolina; Majerski, Kata; Basarić, Nikola
engleski
Synthesis and photochemical reactivity of phthalimidoadamantane-tyrosine conjugates
Dipeptide 3, tetrapeptide 4 and pentapeptide 5, containing adamantylphthalimide and tyrosine, were synthesized and their photochemical reactivity investigated. Upon excitation to the triplet excited state, 3 does not give any photoproduct, although the photoinduced electron transfer (PET) should take place based on the thermodynamic properties. Tetrapeptide 4 and pentapeptide 5 are photochemically reactive, undergoing decomposition upon excitation. The lack of anticipated photodecarboxylation reactivity is explained by PET between the tyrosine and the phthalimide. However, deprotonation of the phenoxyl radical-cation giving phenoxyl radicals or back electron transfer giving starting material are probably faster than intrastrand single electron transfer that would lead to carboxyl radical and decarboxylation. The results indicate importance of fine-tuning molecular structure to attain the desired photoreactivity by right choice of the reactants redox potential, as well as their acid/base properties.
phthalimid ; tyrosine ; peptides ; photodecarboxylation ; photoinduced electron transfer
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
Podaci o izdanju
43 (10)
2017.
5305-5320
objavljeno
0922-6168
1568-5675
10.1007/s11164-017-2927-2