Repozytorium

Stapling of leu-enkephalin analogs with bifunctional reagents for prolonged analgesic activity

Autorzy

Monika Kijewska

Grzegorz Wołczański

Piotr Kosson

Robert Wieczorek

Marek Lisowski

Piotr Stefanowicz

Rok wydania

2024

Czasopismo

Chemical Communications

Numer woluminu

60

Strony

3023-3026

DOI

10.1039/d3cc06345c

Kolekcja

Naukowa

Język

Angielski

Typ publikacji

Artykuł

Streszczenie

The design and synthesis of leu-enkephalin analogs by replacing the glycine residues with N-(2-thioethyl)glycines and opening the cyclisation potential is presented. The cyclization (stapling) was achieved using bifunctional reagents (hexafluorobenzene and trithiocyanuric acid derivatives). The CD conformational studies of the stapled analogs suggest that the peptides adopt the type I β-turn conformation, which is in agreement with the theoretical analysis. The analog containing a trithiocyanuric acid derivative with a benzyl substituent shows potent analgesic activity.

Adres publiczny

http://dx.doi.org/10.1039/D3CC06345C

Strona internetowa wydawcy

https://www.rsc.org/