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Hydrogen Bonding Drives Helical Chirality via 10-Membered Rings in Dipeptide Conjugates of Ferrocene-1,1′-Diamine

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

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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
Project titleProject leaderProject codeProject type
Ferocenski analozi biomolekula: strukturna karakterizacija i biološka evaluacijaBarišić, LidijaIP-2020-02-9162HRZZ
Depositing User: Krešimir Molčanov
Date Deposited: 03 Apr 2023 13:09
DOI: 10.3390/ijms232012233

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