Conformational, Electrochemical, and Antioxidative Properties of Conjugates of Different Ferrocene Turn-Inducing Scaffolds with Hydrophobic Amino Acids

Kovačević, Monika; Roca, Sunčica; Jadreško, Dijana; Mrvčić, Jasna; Hanousek Čiča, Karla; Čakić Semenčić, Mojca; Barišić, Lidija (2024) Conformational, Electrochemical, and Antioxidative Properties of Conjugates of Different Ferrocene Turn-Inducing Scaffolds with Hydrophobic Amino Acids. Inorganics, 12 (7). ISSN 2304-6740

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Abstract

The incorporation of different ferrocene scaffolds into the peptide sequences induces the formation of hydrogen-bond-based secondary structural elements that are frequently observed in natural peptides and proteins. There are three simple ferrocene scaffolds for conjugation with amino acids and peptides that serve as templates for ferrocene peptidomimetics, namely ferrocene-1,1′-dicarboxylic acid (Fcd, I), 1′-aminoferrocene-1-carboxylic acid (Fca, III), and ferrocene-1,1′-diamine (Fcda, V). Here, we have investigated their ability to induce the turn structure upon conjugation with Val, Leu, and Phe. Furthermore, we also wanted to determine whether the branched side chains of Val, Leu, and Phe interfere with intramolecular hydrogen bonding (IHB). For these purposes, we performed a detailed spectroscopic analysis by measuring the concentration, temperature, and solvent dependence of the IR, NMR, and CD spectra. The effect of the different ferrocene scaffolds on the antioxidant activity of the prepared peptides was tested using the DPPH and ABTS methods, and was further rationalized using electrochemical measurements. It was found that the ferrocene scaffold has the greatest influence on the hydrogen bonding pattern, while the influence of the side branches of the amino acids is less relevant.

Item Type:	Article
Uncontrolled Keywords:	ferrocene; peptidomimetics; antioxidant activity; valine; leucine; phenylalanine; conformational analysis; hydrogen bonds; cyclic voltammetry
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division for Marine and Enviromental Research NMR Center
Projects:	Project title Project leader Project code Project type Ferocenski analozi biomolekula: strukturna karakterizacija i biološka evaluacija-FER-AN-BIOMOL Lidija Barišić; Vesna Petrović-Peroković; Željka Car; Rosana Ribić; Marija Lovrić; Adriana Lepur IP-2020-02-9162 HRZZ
Depositing User:	Ivana Vuglec
Date Deposited:	13 Oct 2025 08:36
URI:	http://fulir.irb.hr/id/eprint/9992
DOI:	10.3390/inorganics12070195

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