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Pregled bibliografske jedinice broj: 970127

Časopis

Autori: Sohora, Margareta; Vazdar, Mario; Sović, Irena; Mlinarić-Majerski, Kata; Basarić, Nikola
Naslov: Photocyclization of tetra- and pentapeptides containing adamantylphthalimide and phenylalanines: reaction efficiency and diastereoselectivity
Izvornik: Journal of organic chemistry (0022-3263) 83 (2018); 14905-14922
Vrsta rada: članak
Ključne riječi: cyclic peptides ; decarboxylation ; photochemistry ; phthalimides: photoinduced electron transfer
Sažetak:
A series of tetrapeptides and pentapeptides was synthesized bearing a phthalimide chromophore at the N-terminus. The C-terminus of the peptides was strategically substituted with an amino acid, Phe, Phe(OMe) or Phe(OMe)2 characterized by different oxidation potential. The photochemical reactivity of the peptides was investigated by preparative irradiations and isolation of photoproducts, as well as with laser flash photolysis. Upon photoexcitation, the peptides undergo photoinduced electron transfer (PET) and decarboxylation, followed by diastereoselective cyclization with the retention of configuration for tetrapeptides, or inversion of configuration for pentapeptides. Molecular dynamics (MD) simulations and NOE experiments enabled assignment of the stereochemistry of the cyclic peptides. MD simulations of the linear peptides disclosed conformational reasons for the observed diastereoselectivity, being due to the peptide backbone spatial orientation imposed by the Phe amino acids. The photochemical efficiency for the decarboxylation and cyclization is not dependant on the peptide length, but it depends on the oxidation potential of the amino acid at the C-terminus. The results described herein are particularly important for the rational design of efficient photochemical reactions for the preparation of cyclic peptides with the desired selectivity.
Projekt / tema: HRZZ-IP-2014-09-6312
Izvorni jezik: ENG
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bazama podataka:
Current Contents Connect (CCC)
MEDLINE
Scopus
Arts & Humanities Citation Index (A&HCI) (sastavni dio Web of Science Core Collectiona)
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: https://pubs.acs.org/doi/10.1021/acs.joc.8b01785
Broj citata:
Altmetric:
DOI: 10.1021/acs.joc.8b01785
URL cjelovitog teksta:
Google Scholar: Photocyclization of tetra- and pentapeptides containing adamantylphthalimide and phenylalanines: reaction efficiency and diastereoselectivity
Upisao u CROSBI: Enidija Lukša (Enidija.Luksa@irb.hr), 23. Stu. 2018. u 11:57 sati



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