Synthesis and structural characterization of metallated bioconjugates: C-terminal labeling of amino acids with aminoferrocene

Jios, Jorge L.; Kirin, Srećko I.; Buceta, Norma Nelida; Weyhermüller, Thomas; Védova, Carlos O. Della; Metzler‐Nolte, Nils

doi:10.1016/j.jorganchem.2007.06.044

Cited by 23 publications

(17 citation statements)

References 27 publications

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“…Peptides 1 – 4 were prepared by stepwise solution‐phase peptide synthesis from N ‐Boc‐protected aminoferrocene by the procedure described in ref . Conformational analysis was performed for solutions in nonpolar solvents and in the solid state.…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, the conformational properties of peptides derived from aminoferrocene and natural amino acids are poorly examined. The lowest homologues of these bioconjugates (Boc–AA–NH–Fc; AA = Gly, Leu, Phe, Val, Cys, Tyr; Boc = tert ‐butyloxycarbonyl) do not adopt folded conformations stabilized by intramolecular hydrogen bonds in solution or in the solid state . Our group has recently shown that conjugates derived from aminoferrocene and homochiral dipeptides I [ t BuCO–(AA) 2 –NHFc, AA = Gly, l ‐Ala, l ‐Val] are stabilized by ten‐membered hydrogen‐bonded rings between the NH group closest to the ferrocene unit and the urethane carbonyl group (Figure ) .…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

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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“…Because of the redox potential of the ferrocene, different types of organic materials which contain ferrocene moiety were prepared and used in several applications [1][2][3][4][5][6][7]. On the other hand, some ligands and complexes including ferrocene moiety were prepared for the inorganic applications [8][9][10][11].…”

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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“…Peptide coupling synthesis was studied with ferrocenylmethyl (Fem) amino acids [248 -250], with Mo(allyl) (CO) 2 (R-hist) [265], with (η 5 [249]. Alternatively, aminoferrocene has been attached to the C terminus of amino acids to give Boc-amino acid amides Boc-Aaa-NHFc [268]. groups [269] (Scheme 12).…”

Section: Organometallic Protecting Groupsmentioning

confidence: 99%

Metal Complexes of Biologically Important Ligands, CLXXII [1]. Metal Ions and Metal Complexes as Protective Groups of Amino Acids and Peptides – Reactions at Coordinated Amino Acids

Beck

2009

Zeitschrift Für Naturforschung B

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The introduction of protective groups into multifunctional molecules, e. g. into amino acids for peptide synthesis, and their removal are one of the most important techniques and strategies in Organic Chemistry [2]. Amino acids, their anions and derivatives are versatile ligands, and the leading idea to protect the N- or C-terminus of amino acids by metal ions or by metal complexes has opened interesting chapters which reach from classical coordination and bioinorganic chemistry to modern organometallic and bioorganometallic chemistry [3]

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Synthesis and structural characterization of metallated bioconjugates: C-terminal labeling of amino acids with aminoferrocene

Cited by 23 publications

References 27 publications

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

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

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

Metal Complexes of Biologically Important Ligands, CLXXII [1]. Metal Ions and Metal Complexes as Protective Groups of Amino Acids and Peptides – Reactions at Coordinated Amino Acids

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