Journal of Peptide Science

Cover image for Vol. 20 Issue 9

September 2014

Volume 20, Issue 9

Pages i–iii, 669–745

  1. Issue Information

    1. Top of page
    2. Issue Information
    3. Rapid Communications
    4. Research Articles
    1. Issue information (pages i–iii)

      Article first published online: 11 AUG 2014 | DOI: 10.1002/psc.2564

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  2. Rapid Communications

    1. Top of page
    2. Issue Information
    3. Rapid Communications
    4. Research Articles
    1. O-Acyl isopeptide method: development of an O-acyl isodipeptide unit for Boc SPPS and its application to the synthesis of Aβ1-42 isopeptide (pages 669–674)

      Taku Yoshiya, Tsuyoshi Uemura, Takahiro Maruno, Shigeru Kubo, Yoshiaki Kiso, Youhei Sohma, Yuji Kobayashi, Kumiko Yoshizawa-Kumagaye and Yuji Nishiuchi

      Article first published online: 28 MAY 2014 | DOI: 10.1002/psc.2662

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      The O-acyl isopeptide method was developed for the efficient preparation of difficult sequence-containing peptides. Furthermore, development of the O-acyl isodipeptide unit for Fmoc chemistry simplified its synthetic procedure by solid-phase peptide synthesis. Here, we report a novel isodipeptide unit for Boc chemistry, and the unit was successfully applied to the synthesis of amyloid β peptide.

    2. Matrix-assisted peptide synthesis on nanoparticles (pages 675–679)

      Raz Khandadash, Victoria Machtey, Aryeh Weiss and Gerardo Byk

      Article first published online: 2 JUN 2014 | DOI: 10.1002/psc.2664

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      Biocompatible nanoparticles (NPs) are embedded in a magnetic matrix that allows multistep peptide synthesis on the NPs as well as introduction of fluorescent probes. The matrix is discarded at the end of the process, and the NPs are recovered intact with the synthetic peptide and the probe on their surface. The method can be applied to the synthesis of cell-sensing nanoparticles.

  3. Research Articles

    1. Top of page
    2. Issue Information
    3. Rapid Communications
    4. Research Articles
    1. Molecular characterization of a novel hepcidin (HepcD) from Camelus dromedarius. Synthetic peptide forms exhibit antibacterial activity (pages 680–688)

      Mohamed Boumaiza, Aymen Ezzine, Maryse Jaouen, Marie-Agnes Sari and Mohamed Nejib Marzouki

      Article first published online: 3 JUN 2014 | DOI: 10.1002/psc.2644

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      A novel camel hepcidin gene was identified and characterized showing a high homology structure and sequence identity to the human hepcidin-25. Two camel hepcidin-25 analogs, chemically synthesized, exhibit cytotoxic effect against some pathogenic bacterial species to know Bacillus subtilis American Type Culture Collection (ATCC) 11779, Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 8739. The three disulfide bridges [DH3] hepcidin analog shows to be significantly more active than the one disulfide bridge [DH1] peptide analog. [DH3] analog exhibits antibacterial activity against B. subtilis ATCC 11779 and S. aureus ATCC 6538, at the concentration of 15 μM (50 µg/ml) or above at pH 6.2.

    2. Epitope mapping of the N-terminal portion of tissue transglutaminase protein antigen to identify linear epitopes in celiac disease (pages 689–695)

      Margherita Di Pisa, Patrick Buccato, Giuseppina Sabatino, Feliciana Real Fernández, Brunilde Berti, Francesco Cocola, Anna Maria Papini and Paolo Rovero

      Article first published online: 15 MAY 2014 | DOI: 10.1002/psc.2650

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      Mapping of the tissue transglutaminase N-terminal portion (1–230) identified putative linear auto-antigenic epitopes. A library of 23 overlapping peptides was generated by Fmoc/tBu solid-phase peptide synthesis and screened by immunoenzymatic assays. Four peptides are recognized as linear epitopes by IgA autoantibodies circulating in celiac disease patients' sera.

    3. ‘Click’ chemistry synthesis and capillary electrophoresis study of 1,4-linked 1,2,3-triazole AZT-systemin conjugate (pages 696–703)

      Michał Dobkowski, Aleksandra Szychowska, Małgorzata Pieszko, Anna Miszka, Monika Wojciechowska, Magdalena Alenowicz, Jarosław Ruczyński, Piotr Rekowski, Lech Celewicz, Jan Barciszewski and Piotr Mucha

      Article first published online: 28 MAY 2014 | DOI: 10.1002/psc.2653

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      System (Sys), AVQSKPPSKRDPPKMQTD, is a defense peptide hormone involved in the wound response in tomato plant. To investigate whether Sys can transport cargo molecules through plant tissues, a conjugation of the peptide with 3′-azido-2′,3′-dideoxythymidine molecule using click chemistry was carried out. Capacity electrophoresis showed that click chemistry is a fast and efficient method of bioconjugation, and the conjugate is stable and easily translocated through tomato plant tissues.

    4. Captides: rigid junctions between beta sheets and small molecules (pages 704–715)

      Brandon L. Kier and Niels H. Andersen

      Article first published online: 6 JUN 2014 | DOI: 10.1002/psc.2657

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      We investigated the effect of over 60 different monocarboxylic and polycarboxylic acids as integral components of the beta cap structural motif. Upon ligation, the small molecule is rigidly held in a precise, partly buried environment; fold-dependent rigidity sets this strategy apart from currently flexible bioconjugation methods. Applications to catalyst enhancement, drug design, higher-order assembly, and FRET calibration rulers are discussed.

    5. Inhibitory effect of the carnosine–gallic acid synthetic peptide on MMP-2 and MMP-9 in human fibrosarcoma HT1080 cells (pages 716–724)

      Sung-Rae Kim, Tae-Kil Eom and Hee-Guk Byun

      Article first published online: 23 JUN 2014 | DOI: 10.1002/psc.2658

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      The carnosine–gallic acid peptide (CGP) has strongly inhibited migration and invasion in HT1080 cells through the uPA and uPAR signaling pathways to inhibit MMP-2 and -9.

    6. Synthesis of lucifensin by native chemical ligation and characteristics of its isomer having different disulfide bridge pattern (pages 725–735)

      Stancho Stanchev, Zbigniew Zawada, Lenka Monincová, Lucie Bednárová, Jiřina Slaninová, Vladimír Fučík and Václav Čeřovský

      Article first published online: 11 JUN 2014 | DOI: 10.1002/psc.2663

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      Two models of native chemical ligation have been developed: [15 + 25] Ala-Cys and [19 + 21] His-Cys. Acetamidomethyl-deprotection and oxidation of the ligated linear lucifensin with iodine give a mixture of isomeric lucifensins, regarding their disulfide bridges – the isomer with disulfide bonds [C 1–6], [C 3–5], and [C 2–4] is dominating. The disulfide bridges have been corrected to the native positions by treatment with dithiotreitol in weak alkali media and the consequent open air oxidation.

    7. Synthesis, characterization, and biological activity of poly(arginine)-derived cancer-targeting peptides in HepG2 liver cancer cells (pages 736–745)

      Stesha C. Joseph, Brittany A. Blackman, Megan L. Kelly, Mariana Phillips, Michael W. Beaury, Ivonne Martinez, Christopher J. Parronchi, Constantine Bitsaktsis, Allan D. Blake and David Sabatino

      Article first published online: 15 JUN 2014 | DOI: 10.1002/psc.2665

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      Poly(arginine)-derived cancer-targeting peptides (CTPs) were designed to target glucose-regulated protein 78 receptors and internalize within HepG2 liver cancer cells for biological activity. These CTPs were synthesized by Fmoc-based solid-phase peptide synthesis and isolated by liquid chromatography mass spectrometry for structure-activity relationship studies. Circular dichroism spectroscopy demonstrated folded peptide structures that translated to glucose-regulated protein 78 binding selectivity and penetration within HepG2 cells without triggering apoptosis. Thus, poly(arginine)-derived CTPs may be useful delivery vectors in the safe administration of anticancer drugs for targeted forms of cancer therapy.

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