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Pregled bibliografske jedinice broj: 871823

Stereoselectivity in Phthalimide Initiated Photocyclization of Peptides


Sohora, Margareta; Sović, Irena; Mlinarić-Majerski, Kata; Basarić, Nikola
Stereoselectivity in Phthalimide Initiated Photocyclization of Peptides // 25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem 3. simpozij "Vladimir Prelog" / Poreč, Hrvatska
Poreč, Hrvatska, 2017. str. 65-65 (predavanje, međunarodna recenzija, sažetak, znanstveni)


Naslov
Stereoselectivity in Phthalimide Initiated Photocyclization of Peptides

Autori
Sohora, Margareta ; Sović, Irena ; Mlinarić-Majerski, Kata ; Basarić, Nikola

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem 3. simpozij "Vladimir Prelog" / Poreč, Hrvatska / - , 2017, 65-65

Skup
25. HSKIKI

Mjesto i datum
Poreč, Hrvatska, 19-22.04.2017

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Međunarodna recenzija

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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2014-09-6312 - Supramolekulska kontrola fotokemijskih reakcija eliminacije (Nikola Basarić, )

Ustanove
Institut "Ruđer Bošković", Zagreb