The first ferrocene analogues of muramyldipeptide

Barišić, Lidija; Roščić, Maja; Kovačević, Monika; Semenčić, Mojca Čakić; Horvat, Štefica; Rapić, Vladimir

doi:10.1016/j.carres.2011.01.006

Cited by 17 publications

(16 citation statements)

References 50 publications

(43 reference statements)

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“…[23] The most stable were reoptimized in chloroform (using IEF-PCM to describe implicit solvent effects) with the B3LYP method and 6-311+G(d,p) basis set. [29] Boc-AA-Fca-OMe (2a/2b): The syntheses of 2a and 2b were performed according to our recent paper: [9] the fully protected ferrocene amino acid Boc-Fca-OMe [5] (1) was N-deprotected by gaseous HCl in EtOAc to give the hydrochloride salt, which was treated with NEt 3 and coupled with Boc-AA-OH (AA = l-, d-Ala, previously activated by using EDC and HOBt). Quantum mechanical calculations were performed with Gaussian 09, v.A.02.…”

Section: Computational Detailsmentioning

confidence: 99%

“…Thereby, we applied a strategy similar to that conducted previously, [6][7][8][9] based on a comparison of the spectroscopic data of a reference, a model, and the new compounds. Thereby, we applied a strategy similar to that conducted previously, [6][7][8][9] based on a comparison of the spectroscopic data of a reference, a model, and the new compounds.…”

Section: Synthesis and Characterization Of Ferrocene Peptides VIImentioning

confidence: 99%

“…In this connection, the IR data presented in Table 1 imply the nonhydrogen-bonded states of 4-6 and the hydrogen-bonded states of 7-9. [6][7][8][9] Taking their structures into account, intramolecular hydrogen bonding in monosubstituted ferrocene 7 might be achieved in an intrachain manner to lead to tentative conformations A and B, whereas disubstituted 8 and 9 could be stabilized through interchain IHBs ( Figure 4). IR spectroscopic data [a] (cm -1 ) and 1 H NMR chemical shifts [b] of the NH protons (ppm) of 4-9.…”

Section: Ir and Nmr Spectroscopy Of The Reference (4-6) And Model Commentioning

confidence: 99%

“…The ferrocene peptides VII were obtained by coupling C-protected Fca with Boc-L-Ala-OH and Boc-D-Ala-OH, respectively. [29] Boc-AA-Fca-OMe (2a/2b): The syntheses of 2a and 2b were performed according to our recent paper: [9] the fully protected ferrocene amino acid Boc-Fca-OMe [5] (1) was N-deprotected by gaseous HCl in EtOAc to give the hydrochloride salt, which was treated with NEt 3 and coupled with Boc-AA-OH (AA = l-, d-Ala, previously activated by using EDC and HOBt). Double resonance experiments (COSY, NOESY, and HMBC) were performed in order to assist in signal assignment.…”

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confidence: 99%

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Synthesis and Conformational Analysis of Methyl N‐Alanyl‐1′‐aminoferrocene‐1‐carboxylate

et al. 2012

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Structurally different ferrocene peptides I-VI exhibit considerable conformational differences. This study has explored the structural properties of VII [Y-AA-Fca-OMe; Y = di-tert-butyl dicarbonate (Boc), acetyl (Ac); AA = L-Ala, D-Ala; Fca = 1Ј-aminoferrocene-1-carboxylic acid] with an exchanged sequence of constituent amino acids relative to VI (Y-Fca-AA-OMe; Y = Boc, Ac; AA = L-Ala, D-Ala). The ferrocene peptides VII were obtained by coupling C-protected Fca with Boc-L-Ala-OH and Boc-D-Ala-OH, respectively. The Boc protecting groups of the obtained conjugates Boc-AA-Fca-OMe (2a, AA = L-Ala; 2b, AA = D-Ala) were converted to sterically less demanding Ac groups to give Ac-AA-Fca-1820 Avance 300 MHz spectrometer in CDCl 3 solutions with Me 4 Si as the internal standard. Double resonance experiments (COSY, NOESY, and HMBC) were performed in order to assist in signal assignment. CD spectra were recorded using a Jasco-810 spectropolarimeter in CH 3 CN. Molar ellipticity coefficients, [θ], are in degrees, concentration, c, is given in molL -1 , and path length, l, is given in cm, to give units for [θ] of deg cm 2 dmol -1 . Computational Details:The starting geometries of 2a and 3a were generated by the MacroModel v9.8 [26] molecular modeling program using several different search methods and force fields. The conformers were fully optimized at the B3LYP/LanL2DZ level of theory. [23] The most stable were reoptimized in chloroform (using IEF-PCM to describe implicit solvent effects) with the B3LYP method and 6-311+G(d,p) basis set. [24] Iron was modeled using the ECP set LanL2DZ. Quantum mechanical calculations were performed with Gaussian 09, v.A.02. [27] Molecules were visualized using GaussView [28] and Chem 3D (CambridgeSoft, Cambridge, MA) programs. The topological analysis of the selected compounds was performed with the AIM2000 program. [29] Boc-AA-Fca-OMe (2a/2b): The syntheses of 2a and 2b were performed according to our recent paper: [9] the fully protected ferrocene amino acid Boc-Fca-OMe [5] (1) was N-deprotected by gaseous HCl in EtOAc to give the hydrochloride salt, which was treated with NEt 3 and coupled with Boc-AA-OH (AA = l-, d-Ala, previously activated by using EDC and HOBt). After standard workup and TLC-purification, Boc-l-Ala-Fca-OMe (2a) and Boc-d-Ala-Fca-OMe (2b) were obtained as orange resins.

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Section: Computational Detailsmentioning

confidence: 99%

Section: Synthesis and Characterization Of Ferrocene Peptides VIImentioning

confidence: 99%

Section: Ir and Nmr Spectroscopy Of The Reference (4-6) And Model Commentioning

confidence: 99%

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confidence: 99%

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Synthesis and Conformational Analysis of Methyl N‐Alanyl‐1′‐aminoferrocene‐1‐carboxylate

et al. 2012

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“…Ferrocene-based redox active species have already garnered considerable attention due to their small size, good stability, convenient synthetic access, easy chemical modification, relative lipophilicity, and ease of redox tuning. 3,[30][31][32][33][34][35][36][37][38][39][40][41][42] Small molecules based on the ferrocene core have been used extensively as detectors of metal ions and small molecules. [32][33][34][35][36][37][38]43 Systems targeting larger species such as biomolecules have utilized the attachment of large antibodies or immunoglobulins to ferrocene derivatives that have been embedded onto an electrochemical surface.…”

Section: Introductionmentioning

confidence: 99%

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Scarborough

González

Rodich

et al. 2015

JoVE

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Early detection is a key to successful treatment of most diseases, and is particularly imperative for the diagnosis and treatment of many types of cancer. The most common techniques utilized are imaging modalities such as Magnetic Resonance Imaging (MRI), Positron Emission Topography (PET), and Computed Topography (CT) and are optimal for understanding the physical structure of the disease but can only be performed once every four to six weeks due to the use of imaging agents and overall cost. With this in mind, the development of "point of care" techniques, such as biosensors, which evaluate the stage of disease and/or efficacy of treatment in the clinician's office and do so in a timely manner, would revolutionize treatment protocols.1 As a means to exploring ferrocene based biosensors for the detection of biologically relevant molecules 2 , methods were developed to produce ferrocene-biotin bio-conjugates described herein. This report will focus on a biotin-ferrocenecysteine system that can be immobilized on a gold surface. Video LinkThe video component of this article can be found at

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Adamantyl ferrocene derivatives: Antioxidant abilities and effects on model lipid membranes

Štimac

Lapić

Blasina

et al. 2017

Applied Organom Chemis

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A series of homoannularly and heteroannularly substituted adamantyl ferrocene derivatives has been synthesized and their effects on membrane fluidity were investigated using liposomes as the membrane models. The liposome formulations of adamantyl ferrocene derivatives were characterized by using dynamic light scattering, differential scanning calorimetry and fluorescence anisotropy measurements. It was demonstrated that adamantyl ferrocene derivatives incorporated into the liposome significantly affect the structure of the lipid bilayer. The results of the study have revealed that adamantyl ferrocene derivatives, compounds 9–12, partition into the hydrophobic/hydrophilic interface of the membrane, causing a significant decrease in membrane fluidity. The antioxidant potential of synthesized compounds was assessed with DPPH method and it was shown that the examined compounds possess certain antioxidant activity.

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The first ferrocene analogues of muramyldipeptide

Cited by 17 publications

References 50 publications

Synthesis and Conformational Analysis of Methyl N‐Alanyl‐1′‐aminoferrocene‐1‐carboxylate

Synthesis and Conformational Analysis of Methyl N‐Alanyl‐1′‐aminoferrocene‐1‐carboxylate

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Adamantyl ferrocene derivatives: Antioxidant abilities and effects on model lipid membranes

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