Repozytorium
Wyszukaj
Kolekcje
Inne
Applications of biaryl cyclization in the synthesis of cyclic enkephalin analogs with a highly restricted flexibility
Autorzy
Rok wydania
2024
Czasopismo
Numer woluminu
56
Strony
18/1-18/17
DOI
10.1007/s00726-023-03371-5
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
A series of 10 cyclic, biaryl analogs of enkephalin, with Tyr or Phe residues at positions 1 and 4, were synthesized according to the Miyaura borylation and Suzuki coupling methodology. Biaryl bridges formed by side chains of the two aromatic amino acid residues are of the meta–meta, meta–para, para–meta, and para–para configuration. Conformational properties of the peptides were studied by CD and NMR. CD studies allowed only to compare conformations of individual peptides while NMR investigations followed by XPLOR calculations provided detailed information on their conformation. Reliability of the XPLOR calculations was confirmed by quantum chemical ones performed for one of the analogs. No intramolecular hydrogen bonds were found in all the peptides. They are folded and adopt the type IV β-turn conformation. Due to a large steric strain, the aromatic carbon atoms forming the biaryl bond are distinctly pyramidalized. Seven of the peptides were tested in vitro for their affinity for the µ-opioid receptor.
Słowa kluczowe
Cyclization, Biaryl bridges in peptides, Suzuki-Miyaura reaction, NMR, CD, Molecular docking
Licencja otwartego dostępu
Licencja na prawach której można swobodnie kopiować, rozprowadzać, zmieniać i remiksować objęty prawem autorskim utwór (Utwór-przedmiot prawa autorskiego) pod warunkiem podania imienia i nazwiska autora utworu pierwotnego oraz źródła pochodzenia utworu.
Pełny tekst licencji: https://creativecommons.org/licenses/by/3.0/pl/legalcode
Adres publiczny
http://dx.doi.org/10.1007/s00726-023-03371-5
Strona internetowa wydawcy
Podobne publikacje
PEPPSI-type complexes with small NHC ligands obtained according to the new method efficiently catalyzed Suzuki-Miyaura reaction.
Sikorski Wojciech, Zawartka Wojciech, Trzeciak Anna M.
Suzuki-Miyaura and Hiyama reactions catalyzed by orthopalladated triarylphosphite complexes.
Błaszczyk Izabela, Trzeciak Anna M.
Rh(0) nanoparticles : synthesis, structure and catalytic application in Suzuki-Miyaura reaction and hydrogenation of benzene.
Gniewek Andrzej, Trzeciak Anna M.