Ferrocenoyl peptides with sulfur-containing side chains: synthesis, solid state and solution structures

Hatten, Xavier de; Weyhermüller, Thomas; Metzler‐Nolte, Nils

doi:10.1016/j.jorganchem.2004.10.002

Cited by 42 publications

(38 citation statements)

References 40 publications

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“…[22,23] The coupling constants for the protons on the substituted Cp rings were not resolved and thus, the signals appeared as broad singlets. The Cp resonances of the cobaltocenium complexes are shifted downfield significantly (d 5.2-6.4 ppm) compared with the spectra of the ferrocenoyl compounds (d 4.2-4.8 ppm).…”

Section: Resultsmentioning

confidence: 99%

Solid‐Phase Synthesis, Characterization, and Antibacterial Activities of Metallocene–Peptide Bioconjugates

et al. 2006

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This work shows how the introduction of an organometallic group enhances and modifies the specificity of biologically active peptides. Ferrocene was chosen as an organometallic group because it has been shown to alter the pharmacodynamic profile of bioactive compounds. A comparison with the isosteric cobaltocenium group allows one to explore the influence of charge and redox potential on the biological activity of the conjugates. Arginine and tryptophan containing peptides H-WRWRWR-NH(2) and H-RWRWRW-NH(2) and the metallocene peptide bioconjugates [M]-C(O)-RWRWR-NH(2) and [M]-C(O)-WRWRW-NH(2), where [M]=[Co(Cp)(C(5)H(4))](+), [Fe(Cp)(C(5)H(4))] were prepared by solid-phase peptide synthesis (SPPS). They were purified by HPLC, characterized by ESIMS and NMR spectroscopy, and tested for antibacterial properties against Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus using the minimum inhibitory concentration (MIC) test. In most cases, no metal-specific activity could be observed. However, the conjugate [Fe(Cp)(C(5)H(4))-C(O)-WRWRW-NH(2)] 6 was found to be particularly effective against the Gram-positive S. aureus. The activity of this metallocene-pentapeptide conjugate (7.1 microM) was even better than the 20 amino acid naturally occurring pilosulin 2, which was used as a positive control. Unlike all other compounds tested, which were most active against the Gram-negative E. coli strain, the ferrocene conjugate 6 was the only compound in this series that was most active against Gram-positive bacteria. Given the health concerns resulting from multidrug resistant S. aureus strains, the incorporation of metallocenes may provide a novel line of attack.

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Section: Resultsmentioning

confidence: 99%

Solid‐Phase Synthesis, Characterization, and Antibacterial Activities of Metallocene–Peptide Bioconjugates

et al. 2006

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“…The importance of helical chirality in these systems was first recognized by Hirao et al [5][6][7][8]. On the basis of these and other data [9][10][11][12], three major conformations of 1, n 0 -disubstituted ferrocenoyl peptides derived from ferrocene dicarboxylic acid can be distinguished (Fig. 1) [13].…”

Section: Introductionmentioning

confidence: 91%

1,n′-Disubstituted ferrocenoyl amino acids and dipeptides: Conformational analysis by CD spectroscopy, X-ray crystallography, and DFT calculations

Kirin

Schatzschneider

Hatten

et al. 2006

Journal of Organometallic Chemistry

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“…On the other hand, some ligands and complexes including ferrocene moiety were prepared for the inorganic applications [8][9][10][11]. Ferrocenoyl amino acids and peptides were prepared using acyl ferrocenes and investigated in detail [12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

FT-IR, NMR spectroscopic and quantum mechanical investigations of two ferrocene derivatives

Alver¹,

Parlak²

2017

Bull. Chem. Soc. Eth.

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ABSTRACT. New ferrocene derivatives as N-(3-piperidin-1-ylpropyl)ferrocenamide and N-(pyridine-3-ylmethyl)ferrocenamide (Fc-3pica) and structural investigations were carried out with 1 H, 13 C, DEPT 45 or 135, HETCOR, COSY NMR and FT-IR spectroscopic techniques. Characterization of Fc-3ppa (FeC19H26N2O) and Fc-3pica (FeC17H16N2O) was also supported by density functional theory (DFT) used by B3LYP functional and 6-31G(d) or 6-311++G(d,p) basis sets. From the combination of all the results, it can be clearly seen that syntheses of Fc-3ppa and Fc-3pica have been successfully achieved. Theoretical values are successfully compared against experimental data and B3LYP method is able to provide satisfactory results for predicting NMR properties and vibrational frequencies of the synthesized ferrocene based systems.

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Ferrocenoyl peptides with sulfur-containing side chains: synthesis, solid state and solution structures

Cited by 42 publications

References 40 publications

Solid‐Phase Synthesis, Characterization, and Antibacterial Activities of Metallocene–Peptide Bioconjugates

Solid‐Phase Synthesis, Characterization, and Antibacterial Activities of Metallocene–Peptide Bioconjugates

1,n′-Disubstituted ferrocenoyl amino acids and dipeptides: Conformational analysis by CD spectroscopy, X-ray crystallography, and DFT calculations

FT-IR, NMR spectroscopic and quantum mechanical investigations of two ferrocene derivatives

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