Journal of Peptide Science

Cover image for Journal of Peptide Science

January 2010

Volume 16, Issue 1

Pages 1–80

  1. Protocols

    1. Top of page
    2. Protocols
    3. Rapid Communications
    4. Research Articles
    1. ‘Sulfo-click’ for ligation as well as for site-specific conjugation with peptides, fluorophores, and metal chelators (pages 1–5)

      Dirk T. S. Rijkers, Remco Merkx, Cheng-Bin Yim, Arwin J. Brouwer and Rob M. J. Liskamp

      Article first published online: 18 NOV 2009 | DOI: 10.1002/psc.1197

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      The ‘sulfo-click’ reaction, which is a metal-free chemoselective amidation reaction involving the reaction of an aminoethane sulfonylazide with a thio acid encompasses a new approach for decorating biologically active peptides or dendrimers with biophysical tags, fluorescent probes, metal chelators, and small peptides.

    2. COMU: A third generation of uronium-type coupling reagents (pages 6–9)

      Ayman El-Faham and Fernando Albericio

      Article first published online: 30 NOV 2009 | DOI: 10.1002/psc.1204

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      A third generation of uronium-type coupling reagent based on ethyl 2-cyano-2-(hydroxyimino)acetate as well as a morpholino carbon skeleton. Performed extremely well in the presence of only 1 equiv. of base, which decrees the racemization level during peptide synthesis. The by-products are water soluble and easily removed. Less hazardous safety profile than HOBt-based reagents.

  2. Rapid Communications

    1. Top of page
    2. Protocols
    3. Rapid Communications
    4. Research Articles
    1. Azide reduction during peptide cleavage from solid support—the choice of thioscavenger? (pages 10–14)

      Philipp E. Schneggenburger, Brigitte Worbs and Ulf Diederichsen

      Article first published online: 30 NOV 2009 | DOI: 10.1002/psc.1202

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      A significant azide to amine conversion during peptide cleavage reaction was revealed for peptide/PNA azides designed for application in conjugation techniques. The reductive potential of standard cleavage conditions was assigned to the thioscavenger fraction and analysed with respect to peptide properties such as position of the azide moiety and polarity as well as variation in cleavage cocktail composition.

  3. Research Articles

    1. Top of page
    2. Protocols
    3. Rapid Communications
    4. Research Articles
    1. Novel analogues of arginine vasopressin containing α-2-indanylglycine enantiomers in position 2 (pages 15–20)

      Anna Kwiatkowska, Małgorzta Śleszyńska, Izabela Derdowska, Adam Prahl, Dariusz Sobolewski, Lenka Borovičková, Jiřina Slaninová and Bernard Lammek

      Article first published online: 18 NOV 2009 | DOI: 10.1002/psc.1189

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      The present study describes the synthesis and some pharmacological properties of ten new analogues of arginine vasopressin (AVP) modified at position 2 with α− 2-indanylglycine or its D-enantiomer (Igl or D-Igl, respectively). The Igl2 substitution resulted in a significant change of the pharmacological profile of the peptides. The new analogues were moderate or potent oxytocin antagonists and practically did not interact with V1a and V2 receptors.

    2. Colostrum and bioactive, colostral peptides differentially modulate the innate immune response of intestinal epithelial cells (pages 21–30)

      Ann Louise Worsøe Jørgensen, Helle Risdahl Juul-Madsen and Jan Stagsted

      Article first published online: 10 NOV 2009 | DOI: 10.1002/psc.1190

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      Intact or digested bovine colostrum was tested for bioactivity using murine intestinal cells in absence or presence of various bacterial endotoxins. Reponses to endotoxins in presence of colostrum or LMW fractions were complex with both enhancing and inhibitory effects.

    3. Microwave-assisted TFA cleavage of peptides from Merrifield resin (pages 31–39)

      Alicja Kluczyk, Magdalena Rudowska, Piotr Stefanowicz and Zbigniew Szewczuk

      Article first published online: 10 NOV 2009 | DOI: 10.1002/psc.1191

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      The quick removal of the product from Merrifield resin using a 5 min microwave-assisted TFA reaction makes the analytical scale procedure developed by us a method of choice in monitoring the reactions carried out on Merrifield resin due to the short reaction time and compatibility with HPLC and ESI-MS conditions.

    4. Identification of a novel antitumor peptide based on the screening of an Ala-library derived from the LALF32–51 region (pages 40–47)

      Maribel G. Vallespi, Julio R. Fernandez, Isis Torrens, Isbel Garcia, Hilda Garay, Osmani Mendoza, Milaid Granadillo, Viviana Falcon, Boris Acevedo, Raimundo Ubieta, Gerardo E. Guillen and Osvaldo Reyes

      Article first published online: 11 NOV 2009 | DOI: 10.1002/psc.1192

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      By modifying the primary structure of the Limulus-derived LALF32–51 peptide we designed a novel peptide with antineoplastic effect and cell-penetrating capacity. This new peptide may serve as the prototype of a peptide-based drug with potential applicability in the cancer therapy.

    5. Structure-antigenicity of the V3 region of SIVmac envelope glycoprotein (pages 48–57)

      Fabrice Gaston, Tahar Babas, Faouzi Lakhdar-Ghazal and Elmostafa Bahraoui

      Article first published online: 11 NOV 2009 | DOI: 10.1002/psc.1193

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      As for HIV-1, the V3 region of SIVmac envelope glycoprotein contains an immunodominant linear epitope. But, in contrast to anti-HIV-1 V3 peptide antibodies, antipeptides produced against V3 linear or cyclic peptides were unable to neutralize SIV infection, suggesting a different functional role for the V3 region in the SIV replication cycle.

    6. Novel antimicrobial peptides identified from an endoparasitic wasp cDNA library (pages 58–64)

      Xiaojing Shen, Gongyin Ye, Xiongying Cheng, Chunyan Yu, Hongwei Yao and Cui Hu

      Article first published online: 30 NOV 2009 | DOI: 10.1002/psc.1195

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      We screened an endoparasitic wasp library for DNA sequences having antimicrobial activity using a vital dye exclusion assay. Three screened peptides were synthesized chemically based on the amino acid sequences. These peptides are active against both Gram-negative and -positive bacteria.

    7. On the use of N-dicyclopropylmethyl aspartyl-glycine synthone for backbone amide protection (pages 65–70)

      René Röder, Petra Henklein, Hardy Weißhoff, Clemens Mügge, Michael Pätzel, Ulrich Schubert, Louis A. Carpino and Peter Henklein

      Article first published online: 18 NOV 2009 | DOI: 10.1002/psc.1196

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      To prevent aspartimide formation in particularly Asp-Gly-containing peptides usually the Hmb backbone amide protection is applied for peptide synthesis according to the Fmoc protocols. In the present study, the usefulness of the acid-labile Dcpm protectant was analyzed. Despite the steric hindrance of this group, N-terminal H-(Dcpm)Gly-peptides are quantitatively acylated by potent acylating agents. In this case the new dipeptide Fmoc-Asp(OtBu)-(Dcpm)Gly-OH derivative can be used as a building block. In contrast to the Hmb group, Dcpm is inert toward acylations.

    8. Cellular uptake and biological activity of peptide nucleic acids conjugated with peptides with and without cell-penetrating ability (pages 71–80)

      Yvonne Turner, Gerd Wallukat, Pille Säälik, Burkhard Wiesner, Stephan Pritz and Johannes Oehlke

      Article first published online: 26 NOV 2009 | DOI: 10.1002/psc.1198

      Thumbnail image of graphical abstract

      A 12-mer peptide nucleic acid (PNA) directed against the nociceptin/orphanin FQ receptor mRNA was disulfide bridged with various peptides without and with cell-penetrating features. The cellular uptake and the antisense activity of these conjugates was assessed in parallel. Comparable cellular uptake and biological activity was found for all conjugates and for the naked PNA. The found results suggest cellular uptake and bioactivity of PNA-peptide conjugates to be not primarily related to the cell-penetrating ability of their peptide components.

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