Journal of Peptide Science

Cover image for Vol. 19 Issue 10

October 2013

Volume 19, Issue 10

Pages 607–668

  1. Rapid Communication

    1. Top of page
    2. Rapid Communication
    3. Research Articles
    1. Formation of truncated peptide by-products via sequence-specific formyl group transfer from Trp(For) residues to in the course of Boc-SPPS (pages 607–612)

      Viatcheslav N. Azev, Leila G. Mustaeva, Elena Yu. Gorbunova, Maksim V. Molchanov and Igor L. Rodionov

      Article first published online: 26 AUG 2013 | DOI: 10.1002/psc.2547

      Thumbnail image of graphical abstract

      We describe a set of model experiments that permitted to detect sequence-specific formyl group transfer from Trp(For) residues to alpha-amino group during solid-phase peptide synthesis.

  2. Research Articles

    1. Top of page
    2. Rapid Communication
    3. Research Articles
    1. Syntheses and anti-tubercular activity of β-substituted and α,β-disubstituted peptidyl β-aminoboronates and boronic acids (pages 613–618)

      Alexey S. Gorovoy, Olga Gozhina, John-Sigurd Svendsen, George V. Tetz, Anna Domorad, Victor V. Tetz and Tore Lejon

      Article first published online: 23 AUG 2013 | DOI: 10.1002/psc.2537

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      A number of of peptidyl β-aminoboronic acids and β-aminoboronates have been synthesized and tested in vitro for anti-tubercular activity.

    2. Design of NK-2-derived peptides with improved activity against equine sarcoid cells (pages 619–628)

      Stephanie Gross, Dominik Wilms, Jannike Krause, Gerald Brezesinski and Jörg Andrä

      Article first published online: 25 JUL 2013 | DOI: 10.1002/psc.2540

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      Equine sarcoid and normal skin cells have been evaluated as a model system for topical administration of anticancer peptides. Focus was laid on mammalian peptide NK-2, which rapidly killed sarcoid cancer cells by membrane permeabilisation. A shortened derivative with fivefold improved activity has been designed.

    3. Characterization of endocytic uptake of MK2-inhibitor peptides (pages 629–638)

      Jamie Brugnano, James McMasters and Alyssa Panitch

      Article first published online: 23 AUG 2013 | DOI: 10.1002/psc.2541

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      Flow cytometry and fluorescent colocalization were used to characterize cellular uptake of therapeutic peptides. Results indicate that the addition of a fluorescent label does not impact the peptides' ability to enter the cell, and that cellular uptake occurs through energy-dependent endocytosis. Finally, the mechanism of endocytic uptake is dependent on peptide concentration, cell type, and choice of cell penetrating domain.

    4. Enhanced binding to and killing of hepatocellular carcinoma cells in vitro by melittin when linked with a novel targeting peptide screened from phage display (pages 639–650)

      Honglei Zhao, Xin Feng, Wenyu Han, Yuwen Diao, Dong Han, Xiaofeng Tian, Yu Gao, Shanshan Liu, Seng Zhu, Cuimei Yao, Jingmin Gu, Changjiang Sun and Liancheng Lei

      Article first published online: 26 AUG 2013 | DOI: 10.1002/psc.2542

      Thumbnail image of graphical abstract

      We successfully screened a novel peptide that bound to HepG2 cells and is a valuable ligand for tumor targeting that leads to an increased binding and killing effect of hepatocellular carcinoma cells in vitro when linked to melittin.

    5. Identification of small peptides inhibiting the integrase-LEDGF/p75 interaction through targeting the cellular co-factor (pages 651–658)

      Claudia Cavalluzzo, Frauke Christ, Arnout Voet, Ajendra Sharma, Brajendra Kumar Singh, Kam Y.J. Zhang, Eveline Lescrinier, Marc De Maeyer, Zeger Debyser and Erik Van der Eycken

      Article first published online: 27 AUG 2013 | DOI: 10.1002/psc.2543

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      In this work, we present the design, synthesis, and evaluation of LP21, a short peptide that is able to inhibit the LEDGF/p75-IN interaction at low μM concentration through its binding to the IN binding site of LEDGF/p75. Our discovery could lead to the synthesis of a peptidomimetic with high anti-HIV activity targeting the cellular co-factor LEDGF/p75 and not the viral protein IN.

    6. An efficient method for the synthesis of phenacyl ester-protected dipeptides using neutral alumina-supported sodium carbonate ‘Na2CO3/n-Al2O3 (pages 659–662)

      Chikao Hashimoto, Kazuhiro Sugimoto, Youhei Takahashi and Mitsuo Kodomari

      Article first published online: 28 AUG 2013 | DOI: 10.1002/psc.2544

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      In the synthesis of dipeptides (Boc-AA1-AA2-OPac: AA1 and AA2 represent amino acids) protected by phenacyl (Pac) ester, amines and solid bases as the base for the conversion of the trifluoroacetic acid (TFA) salt of the amino component (TFA·H-AA2-OPac) into the corresponding free amino component (H-AA2-OPac) were examined. The synthesis of a dipeptide (Boc-Ala-Gly-OPac) using neutral alumina-supported Na2CO3 (Na2CO3/n-Al2O3) as a solid base for the conversion provided the dipeptide in a quantitative yield without by-products compared with the synthesis employing amines. The application of Na2CO3/n-Al2O3 to the synthesis of some dipeptides protected by Pac ester gave the desired peptides in excellent yields.

    7. Carbon-11 radiolabeling of an oligopeptide containing tryptophan hydrochloride via a Pictet-Spengler reaction using carbon-11 formaldehyde (pages 663–668)

      Masayuki Hanyu, Yuuki Takada, Hiroki Hashimoto, Kazunori Kawamura, Ming-Rong Zhang and Toshimitsu Fukumura

      Article first published online: 15 AUG 2013 | DOI: 10.1002/psc.2546

      Thumbnail image of graphical abstract

      The radiolabeling of a Trp•HCl-containing RGD peptide using the Pictet-Spengler reaction was successful. Furthermore, the remote-controlled synthesis of a [1-11C]Tpi-containing RGD peptide was attempted by using an automatic production system to generate [11C]CH3I. The radiochemical yield of the [1-11C]Tpi-containing RGD at the end of synthesis was 5.9 ± 1.9% (n = 4), for a total synthesis time of about 35 min.