A5050417973- Ferrocene Chemistry and Applications
- Chemical Synthesis and Analysis
- Molecular Junctions and Nanostructures
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Metal complexes synthesis and properties
- Biopolymer Synthesis and Applications
- Organometallic Compounds Synthesis and Characterization
- Inorganic and Organometallic Chemistry
- Crystallography and molecular interactions
- Crystal structures of chemical compounds
- Advanced biosensing and bioanalysis techniques
- Organometallic Complex Synthesis and Catalysis
- Synthesis and Biological Evaluation
- Organoboron and organosilicon chemistry
- biodegradable polymer synthesis and properties
- RNA Interference and Gene Delivery
- Chemical Synthesis and Characterization
- Analytical Chemistry and Chromatography
- Protein Hydrolysis and Bioactive Peptides
- Synthesis and Characterization of Heterocyclic Compounds
- DNA and Nucleic Acid Chemistry
- PARP inhibition in cancer therapy
- Vitamin C and Antioxidants Research
- Sirtuins and Resveratrol in Medicine
University of Zagreb
2003-2024
Abstract We present a detailed structural study of peptide derivatives 1′‐aminoferrocene‐1‐carboxylic acid (ferrocene amino acid, Fca), one the simplest organometallic acids. Fca was incorporated into di‐ to pentapeptides with D ‐ and L ‐alanine residues attached either carboxy or group, both. Crystallographic spectroscopic studies (circular dicroism (CD), IR, NMR) about two dozen compounds were used gain insight their structures in solid state as well solution. Four characterized by...
The first example of an orthogonally protected ferrocene-1,1′-diamine based peptidomimetic with a stable intramolecular hydrogen bond pattern comprised two β-turns is reported.
Novel organometallic sugar amino acid conjugates 1–5 have been prepared by amide coupling of O-protected N-acetylmuramic and iso-muramic (2-[3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoic acid) with 1-aminoferrocene, 1-aminoferrocene-1′-carboxylic (H-Fca-OH), or 1,1′-diaminoferrocene, respectively. The influence the ferrocenyl moiety presence additional remote potential hydrogen atom acceptors donors at core on conformation lipophilicity is investigated TLC, IR, NMR, CD...
Our previous studies showed that alteration of dipeptides Y-Fca-Ala-OMe (III) into Y-Ala-Fca-OMe (IV) (Y = Ac, Boc; Fca 1'-aminoferrocene-1-carboxylic acid) significantly influenced their conformational space. The novel bioconjugates Y-Fca-Pro-OMe (1, Y Ac; 2, Boc) and Y-Pro-Fca-OMe (3, 4, Ac) have been prepared in order to investigate the influence proline, a well-known turn-inducer, on properties small organometallic peptides with an exchanged constituent amino acid sequences. For this...
The N-termini of the constitutional isomeric ferrocene peptides Boc–NH–Fn–CO–Ala–OMe (1) and Boc–Ala–NH–Fn–COOMe (2) were deprotected in acidic milieu subjected to oxalyl chloride-mediated dimerization afford oxalamides −(CO–NH–Fn–CO–Ala–OMe)2 (3) −(CO–Ala–NH–Fn–COOMe)2 (4), respectively. goal compounds evaluated for their conformational properties, toluene gelation ability, effect on cell viability tumor (HeLa, MCF7, HepG2) normal (HEK293T) lines. Detailed spectroscopic analysis solution...
The synthesis and conformational analysis of a series the monosubstituted aminoferrocene‐based peptides bearing homo‐ heterochiral Pro‐Ala sequences are described. A change Pro amino acid chirality can affect secondary structure. homochiral derivatives t BuCO–AA 2 –AA 1 –NHFc (Fc = ferrocene; AA Pro, Ala) favour β‐turns, disruption structure is observed for analogues in solution. detailed computational study suggested that γ‐turns form derivatives. X‐ray‐determined crystal structures...
Abstract 1,1′‐Disubstituted ferrocene conjugates present useful and efficient bioorganometallic constraint design to reduce the conformational flexibility of small peptides. In this study we first systematic analysis nonsymmetric peptidomimetics (Boc‐AA‐NH‐Fn‐COMe; Boc = tert ‐butoxycarbonyl; AA Gly, L ‐Ala, ‐Val; Fn 1,1′‐ferrocenylene) their monosubstituted analogues (Boc‐AA‐NH‐Fc; Fc ferrocenyl; ‐Val). The spectroscopic data (IR, NMR CD) were corroborated by DFT calculations indicated...
The development of turn-based inhibitors protein–protein interactions has attracted considerable attention in medicinal chemistry. Our group synthesized a series peptides derived from an amino-functionalized ferrocene to investigate their potential mimic protein turn structures. Detailed DFT and spectroscopic studies (IR, NMR, CD) have shown that, for peptides, the backbone chirality bulkiness amino acid side chains determine hydrogen-bond pattern, allowing tuning size preferred...
The chirality of the protein backbone influences both self-assembly and biological activity. In ferrocene-containing peptides, sequence constitutive amino acids as well structure ferrocene scaffold strongly influence conformational properties, whereas activity is more influenced by lipophilicity. A joint spectroscopic computational study has shown that a relatively simple structural modification, such changing order two in dipeptide from Pro–Ala (III) to Ala–Pro (IV), also alters hydrogen...
tert ‐Butyl‐1′‐methoxycarbonyl‐1‐ferrocenecarbamate ( 1 ) was Boc‐deprotected to give free amine which underwent oxalyl chloride‐mediated dimerization. The structure of the so‐obtained oxalamide‐bridged ferrocene 2 elucidated using infrared and NMR H, 13 C, COSY, NOESY, HSQC, HMBC) spectroscopies, crystal analysis, electrospray ionization high‐resolution mass spectrometry. preliminary conformational analysis in solution suggested intramolecular engagement oxalamide protons, while...
Polychlorinated biphenyls (PCBs) can induce neurotoxicity, immunotoxicity, reproductive toxicity, genotoxicity, and carcinogenicity (IARC group 1 Carcinogens). Scientific data suggest that resveratrol possesses the ability to attenuate ortho-PCB-induced toxicity. Recently, a novel ferrocene-containing triacyl derivative of (RF) was synthesized in this study, its potential protect CHO-K1 cells from selected PCB congeners (75 µM) evaluated. Cell viability/proliferation observed by Trypan Blue...
The main structural feature of the title compound, [Fe(C7H8NO)(C7H7O2)], is existence strong intermolecular hydrogen bond N—H⋯O=C type between amide N—H group and carbonyl O atom COOCH3 from an adjacent molecule [2.934 (2) Å]. acetamide participates as a double proton acceptor in bonds C—H⋯O [3.411 3.506 Å], thus forming three-dimensional network. cyclopentadienyl rings, which are parallel to each other within 1.04 (9)°, twisted eclipsed conformation by only 3.92 (1)° (maximum)....