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Pregled bibliografske jedinice broj: 871823

Zbornik radova

Autori: Sohora, Margareta; Sović, Irena; Mlinarić-Majerski, Kata; Basarić, Nikola
Naslov: Stereoselectivity in Phthalimide Initiated Photocyclization of Peptides
Izvornik: 25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem 3. simpozij "Vladimir Prelog" / Poreč, Hrvatska
Skup: 25. HSKIKI
Mjesto i datum: Poreč, Hrvatska, 19-22.04.2017.
Ključne riječi: peptides, phthalimide, photochemistry, stereoselectivity
Sažetak:
Phthalimide in the triplet excited state is a good oxidizing agent. Therefore, upon photoexcitation of the phthalimide to the triplet state, alkyl-carboxylates are easily oxidized by inter- or intramolecular single electron transfer (SET) from the carboxylate to the phthalimide [1]. The SET promotes irreversible decarboxylation leading to radical intermediates, which was implemented in different synthetic applications. For example, such a decarboxylation has been used in the photocyclization of crown ethers or peptides [1, 2]. We have become interested in photoinduced decarboxylation reactions of different phthalimide derivatives of adamantane aminoacids [3, 4]. Within the scope of that research, we have found an example of highly enantioselective dipeptide cyclization with a memory of chirality [5]. In the continuation of the research we investigated photocyclization of tetra- and pentapeptides 1-6 (Scheme 1). The photocyclizations of 1-6 to peptides 7-12 proceed in moderate yields, but with high diastereoselectivity. Interestingly, preliminary results indicate different stereochemistry in the cyclic products in tetra- and pentapeptides and suggest that the chiral information in the peptide chains leads to a complete inversion or retention of configuration.
Vrsta sudjelovanja: Predavanje
Vrsta prezentacije u zborniku: Sažetak
Vrsta recenzije: Međunarodna recenzija
Projekt / tema: HRZZ-IP-2014-09-6312
Izvorni jezik: ENG
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL Internet adrese: http://25hskiki.org/hr/naslovnica/
Upisao u CROSBI: Enidija Lukša (Enidija.Luksa@irb.hr), 24. Tra. 2017. u 10:43 sati



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