Naslov
Synthesis and photochemical reactivity of phthalimidoadamantane-tyrosine conjugates

Autori
Sohora, Margareta ; Vidović, Nikolina ; Mlinarić-Majerski, Kata ; Basarić, Nikola

Izvornik
Research on chemical intermediates (0922-6168) 43 (2017), 10; 5305-5320

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Phthalimide, Tyrosine, Peptides, Photodecarboxylation, Photoinduced electron transfer

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA