Synthesis and Conformational Study of Bioconjugates Derived from 1‐Acetyl‐1′‐aminoferrocene and α‐Amino Acids

Semenčić, Mojca Čakić; Kovač, Veronika; Kodrin, Ivan; Barišić, Lidija; Rapić, Vladimir

doi:10.1002/ejic.201402837

Cited by 12 publications

(16 citation statements)

References 35 publications

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“…The DFT analysis results that predicted three IHB motifs A-C were compatible with NMR data (Figure 17 Bioconjugates 33-35 (Boc-AA-NH-Fn-COMe; AA = Gly, L-Ala, L-Val) [77] and 39-41 [Boc-(AA)2-NH-Fn-COMe; AA = Gly, L-Ala, L-Val] [78] , derived by N-terminal elongation of Boc-NH-Fn-COMe, can also be considered as nonsymmetric analogues of ferrocene-containing peptidomimetics IV (Scheme 6). These derivatives were subjected to detailed CD, IR and NMR spectroscopic analysis, combined with theoretical investigation (DFT), to describe their preferred conformations in solution.…”

Section: Bioconjugates Of 1'-aminoferrocene-1carboxylic Acid and Alansupporting

confidence: 69%

Ferrocene Bioconjugates

Semenčić¹,

Barišić²

2017

Croat. Chem. Acta

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In this review we present our recent contribution to the field of bioorganometallic chemistry of ferrocene. Ferrocene conjugates with biomolecules have been synthesized and characterized using IR and NMR (1 H, 13 C, COSY, NOESY, HMBC) spectroscopy, ESI-MS and HRMS. The bioconjugates of ferrocene with resveratrol (2) and mannose (10, 11, 14 and 15) were biologically evaluated for their potential inhibitory effect on HepG2 cancer cells (2) and E. coli adherence to the bladder epithelium (10, 11, 14 and 15). The oxalamide-bridged ferrocene 17 was subjected to conformational analysis in solution and in the solid state, and tested for its gelation and cytotoxic activity.

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Section: Bioconjugates Of 1'-aminoferrocene-1carboxylic Acid and Alansupporting

confidence: 69%

Ferrocene Bioconjugates

Semenčić¹,

Barišić²

2017

Croat. Chem. Acta

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“…The research described in our previous papers usually includes a computational study to obtain a complete picture regarding the hydrogen bonding in ferrocene derivatives , , , , . Here, we again employed an approach in which molecular and quantum mechanics are combined to achieve a relatively fast search of the conformational space.…”

Section: Resultsmentioning

confidence: 99%

“…The research described in our previous papers usually includes a computational study to obtain a complete picture regarding the hydrogen bonding in ferrocene derivatives. [9,32,33,34,35] Here, we again employed an approach in which molecular and quantum mechanics are combined to achieve a relatively fast search of the conformational space. DFT calculations were performed with the B3LYP functional with <zfigr13" pos="x22>Grimme dispersion corrections combined with the Pople basis set 6-311+G(d,p) and the effective core potential (ECP) basis set LanL2DZ for iron atoms.…”

Section: Computational Studymentioning

confidence: 99%

Synthesis and Conformational Study of Monosubstituted Aminoferrocene‐Based Peptides Bearing Homo‐ and Heterochiral Pro‐Ala Sequences

et al. 2016

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Abstract:The synthesis and conformational analysis of a series of the monosubstituted aminoferrocene-based peptides bearing homo-and heterochiral Pro-Ala sequences are described. A change of the Pro amino acid chirality can affect the secondary structure. The homochiral derivatives of tBuCO-AA 2 -AA 1 -NHFc (Fc = ferrocene; AA = Pro, Ala) favour -turns, and a disruption of the secondary structure is observed for the heterochiral analogues in solution. A detailed computational study suggested that γ-turns form in the heterochiral derivatives. The X-ray-de-

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“…The conformation and hydrogen‐bonding properties of ferrocenyl‐labeled sugar amino acids were also examined by Barisic's and Rapic's groups. The Rapic and Zinic group established the formation of foldamers stabilized by the special type of aromatic π–π interactions between the closer cyclopentadienyl rings of the juxtaposed ferrocene units of bis‐ and tris(ferrocene)‐containing N ‐methylimides …”

Section: Ferrocenes In Supramolecular Ensembles Liquid Crystals Andmentioning

confidence: 99%

Why is Ferrocene so Exceptional?

2016

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The appearance of ferrocene in the middle of the 20th century has revolutionized organometallic chemistry and is now providing applications in areas as varied and sometimes initially unexpected as optical and redox devices, battery and other materials, sensing, catalysis, including asymmetric and enantioselective catalysis, and medicine. The author presents here a general, although personal, view of ferrocene's chemistry, properties, functions, and applications through a literature survey involving both historical and up‐to‐date trends and including examples of his group's research in a number of these areas. The review gathers together general features of ferrocene chemistry and representative examples of the salient aspects. Its focus is on ferrocene's basic properties, ferrocene‐containing ligands, the ferrocene/ferricinium redox couple, ferrocene mixed‐valence and average‐valence systems, the ferricinium/ferrocene redox shuttle in catalysis, ligand‐exchange reactions, ferrocene‐containing polymers, ferrocene‐containing structures for cathodic battery and other materials, ferrocenes in supramolecular ensembles, liquid crystals, and nonlinear optical materials, ferrocene‐containing stars and their electrostatic effects, ferrocene‐containing dendrons, dendrimers, and nanoparticles (NPs) and their application in redox sensing and catalysis, and ferrocenes in nanomedicine.

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Synthesis and Conformational Study of Bioconjugates Derived from 1‐Acetyl‐1′‐aminoferrocene and α‐Amino Acids

Cited by 12 publications

References 35 publications

Ferrocene Bioconjugates

Ferrocene Bioconjugates

Synthesis and Conformational Study of Monosubstituted Aminoferrocene‐Based Peptides Bearing Homo‐ and Heterochiral Pro‐Ala Sequences

Why is Ferrocene so Exceptional?

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