Hrvatska znanstvena bibliografija (CROSBI)



Pregled bibliografske jedinice broj: 863968

Časopis

Autori: Sohora, Margareta; Vidović, Nikolina; Mlinarić-Majerski, Kata; Basarić, Nikola
Naslov: Synthesis and photochemical reactivity of phthalimidoadamantane-tyrosine conjugates
Izvornik: Research on chemical intermediates (0922-6168) 43 (2017), 10; 5305-5320
Vrsta rada: članak
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.
Projekt / tema: HRZZ-IP-2014-09-6312
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL Internet adrese: http://link.springer.com/article/10.1007%2Fs11164-017-2927-2
Broj citata:
Altmetric:
DOI: 10.1007/s11164-017-2927-2
URL cjelovitog teksta:
Google Scholar: Synthesis and photochemical reactivity of phthalimidoadamantane-tyrosine conjugates
Upisao u CROSBI: Enidija Lukša (Enidija.Luksa@irb.hr), 1. Ožu. 2017. u 09:45 sati