Kovačević, Monika; Markulin, Dora; Zelenika, Matea; Marjanović, Marko; Lovrić, Marija; Polančec, Denis; Ivančić, Marina; Mrvčić, Jasna; Molčanov, Krešimir; Milašinović, Valentina; Roca, Sunčica; Kodrin, Ivan; Barišić, Lidija (2022) Hydrogen Bonding Drives Helical Chirality via 10-Membered Rings in Dipeptide Conjugates of Ferrocene-1,1′-Diamine. International Journal of Molecular Sciences, 23 (20). ISSN 1422-0067
|
PDF
- Published Version
- article
Available under License Creative Commons Attribution. Download (2MB) | Preview |
Abstract
Considering the enormous importance of protein turns as participants in various biological events, such as protein–protein interactions, great efforts have been made to develop their conformationally and proteolytically stable mimetics. Ferrocene-1, 1′-diamine was previously shown to nucleate the stable turn structures in peptides prepared by conjugation with Ala (III) and Ala–Pro (VI). Here, we prepared the homochiral conjugates of ferrocene-1, 1′-diamine with l-/d-Phe (32/35), l-/d-Val (33/36), and l-/d-Leu (34/37) to investigate (1) whether the organometallic template induces the turn structure upon conjugation with amino acids, and (2) whether the bulky or branched side chains of Phe, Val, and Leu affect hydrogen bonding. Detailed spectroscopic (IR, NMR, CD), X-ray, and DFT studies revealed the presence of two simultaneous 10-membered interstrand hydrogen bonds, i.e., two simultaneous β-turns in goal compounds. A preliminary biological evaluation of d-Leu conjugate 37 showed its modest potential to induce cell cycle arrest in the G0/G1 phase in the HeLa cell line but these results need further investigation.
| Item Type: | Article | ||||||||
|---|---|---|---|---|---|---|---|---|---|
| Uncontrolled Keywords: | biological activity ; chirality ; conformational analysis ; Density Functional Theory (DFT) ; ferrocene ; hydrogen bonds ; peptidomimetic ; X-ray | ||||||||
| Subjects: | NATURAL SCIENCES > Chemistry | ||||||||
| Divisions: | Division of Physical Chemistry NMR Center |
||||||||
| Projects: |
|
||||||||
| Depositing User: | Krešimir Molčanov | ||||||||
| Date Deposited: | 03 Apr 2023 13:09 | ||||||||
| URI: | http://fulir.irb.hr/id/eprint/7824 | ||||||||
| DOI: | 10.3390/ijms232012233 |
Actions (login required)
 |
View Item |
Altmetric
Altmetric
