Naslov
Photochemistry of phthalimidoadamantane dipeptides: efectof amino acid side chain on photocyclization
(Photochemistry of phthalimidoadamantane dipeptides: efect of amino acid side chain on photocyclization)

Autori
Sohora, Margareta ; Sović, Irena ; Spahić, Zlatan ; Kontrec, Darko ; Jurin, Mladenka

Vrsta, podvrsta
Radovi u časopisima, znanstveni

Izvornik
Photochemical & photobiological sciences (2023)

Status rada
Online first

Ključne riječi
Cyclic peptides ; Phthalimides ; Photochemistry ; Stereoselective cyclization

Sažetak
A series of dipeptides 1 was synthesized that at the N-site contained 3-(N-phthalimidoadamantane-1- carboxylic acid and at the C-site different aliphatic or aromatic l- or d-amino acids. The photochemical reaction of dipeptides 1 under acetonesensitized conditions gave simple decarboxylation products 6, and decarboxylation-induced cyclization products 7, as well as some secondary products 8 and 9 formed by elimination of H2O or ring enlargement, respectively. Molecules 9 undergo secondary photoinduced H-abstractions by the phthalimide chromophore, delivering more complex polycycles 11. The photodecarboxylation-induced cyclization to 7 was observed only with phenylalanine (Phe), proline (Pro), leucine (Leu) and isoleucine (Ile). Contrary to dipeptides with Phe, the cyclization takes place with almost complete racemization at the amino acid chiral center, but diastereoselectively giving only one pair of enantiomers. The conducted investigation is important as it provides the breath and the scope of dipeptide cyclizations activated by phthalimides.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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