β-ferrocenylalanyl peptides

Cuingnet, E.; Sergheraert, Christian; Tartar, André; Dautrevaux, M

doi:10.1016/s0022-328x(00)93315-1

Cited by 39 publications

(29 citation statements)

References 11 publications

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“…In the 1980 s some ferrocenyl peptides and half-sandwich peptide complexes were isolated in low yields because of problems with decomposition. [29][30][31][32][33][34][35][36] More recently, labeling of DNA with ferrocene has been reported. [37][38][39][40][41] The solid-phase synthesis of Mo carbonyl complexes have also been reported; without biomolecules [42][43][44] and with [Leu 5 ]-enkephalin.…”

Section: Discussionmentioning

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: Discussionmentioning

confidence: 99%

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

et al. 2006

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“…Twenty years ago, a few papers were published dealing with the application of SPPS to metallocenes. Ferrocenylalanine (Fer) and cymantrenylalanine (Cym) were incorporated [ [18][19][20][21] It is worth to mention SPPS of a "ferrocenophanic" conformationally constrained analogue of substance P. [22] Very recently, SPPS of N-terminated cobaltocenium-NLS peptides [23] and metallocenoyl (M = Fe, Co) tripeptides [24] with antibacterial activity were described by one of us. In all peptides described up to the present day, the organometallic group is part of the side chain or linked to the N-terminus.…”

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confidence: 99%

“…The total decomposition of Fmoc-Fca-Ala-Gly-Val-Leu-resin upon removal of the protecting group led us to terminate this peptide with BocFca which is a convenient intermediate either for further elongation of the peptide chain by Fmoc-protected amino acids to yield 3 or for its successfully cleavage from the resin (for 2). The target molecules of previously reported SPPS with metallocenes were: (i) bioconjugates obtained by replacement of one or two Phe "internal" subunits by metallocenylalanine or (metallocene-1,1Ј-diyl)bis(alanine), [18][19][20][21][22] (ii) N-metallocenoyl terminated peptide sequences. [23,24] In this paper, we show that it is possible to incorporate the unnatural ferrocene amino acid Fca into the peptide backbone by SPPS.…”

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confidence: 99%

Incorporation of the Unnatural Organometallic Amino Acid 1′‐Aminoferrocene‐1‐carboxylic Acid (Fca) into Oligopeptides by a Combination of Fmoc and Boc Solid‐Phase Synthetic Methods

2006

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The organometallic amino acid 1′‐aminoferrocene‐1‐carboxylic acid (Fca) was incorporated internally into a peptide sequence by solid‐phase methods combining natural Fmoc‐protected amino acids and Boc‐Fca‐OH to give the pentapeptide Boc‐Fca‐Ala‐Gly‐Val‐Leu‐NH2 (2) and the octapeptide Ac‐Val‐Gly‐Ala‐Fca‐Ala‐Gly‐Val‐Leu‐NH2 (3). Compound 3 was found to have a helically ordered structure by NMR and CD spectroscopy, which is stabilized by intramolecular hydrogen bonding in an antiparallel β‐sheet‐like arrangement. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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“…[97] Some of these metalloamino acids are sufficiently stable under aqueous and ambient conditions and can be employed in SPPS. [67][68][69][70][71] [ [67][68][69] Two Fer amino acids were coupled to a Glu 4 tetrapeptide (Scheme 16, 40). [70] As expected, considering the large Fe-Fe distance, the two ferrocene units in 40 are electrochemically insulated from each other.…”

Section: Sps Of Transition-metal-containing Peptides: Formation Of Comentioning

confidence: 99%

Solid‐Phase Synthesis of Transition‐Metal Complexes

Heinze

Beckmann

Hempel

2008

Chemistry A European J

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This overview highlights recent progress in the field of selective construction of linear, oligonuclear transition-metal complexes by using solid-phase synthesis procedures. Two general protocols have been identified: formation of coordinative bonds between metal centres and bridging ligands and formation of covalent bonds between preformed kinetically inert transition-metal-containing building blocks in the chain growth step. Currently available suitable building blocks for the second approach are based on ferrocene units, bis(terpyridine)-ruthenium(II) moieties or metal porphyrins.

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β-ferrocenylalanyl peptides

Cited by 39 publications

References 11 publications

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

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

Incorporation of the Unnatural Organometallic Amino Acid 1′‐Aminoferrocene‐1‐carboxylic Acid (Fca) into Oligopeptides by a Combination of Fmoc and Boc Solid‐Phase Synthetic Methods

Solid‐Phase Synthesis of Transition‐Metal Complexes

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