Journal of Peptide Science

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Award Lectures

Journal of Peptide Science > 16 > S1 > 22 - 25

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Posters

Journal of Peptide Science > 16 > S1 > 48 - 206

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Young Investigator Oral Abstracts

Journal of Peptide Science > 16 > S1 > 44 - 47

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Oral abstracts

Journal of Peptide Science > 16 > S1 > 26 - 43

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Structure‐antigenicity of the V3 region of SIVmac envelope glycoprotein

Fabrice Gaston, Tahar Babas, Faouzi Lakhdar‐Ghazal, Elmostafa Bahraoui

Journal of Peptide Science > 16 > 1 > 48 - 57

The objective of this study was to analyze the immunogenicity and antigenicity of the V3 domain (Cys313–Cys346) of the external envelope glycoprotein gp125 of SIVmac251. The corresponding peptide was synthesized and characterized as linear and cyclic peptides. Our results showed that this region, as for HIV‐1, contained an immunodominant epitope. The antigenicity was similar for the linear and cyclic...

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Azide reduction during peptide cleavage from solid support—the choice of thioscavenger?

Philipp E. Schneggenburger, Brigitte Worbs, Ulf Diederichsen

Journal of Peptide Science > 16 > 1 > 10 - 14

Peptide azides acquired growing impact because of application in bioconjugation via ‘click chemistry’ or Staudinger ligation. Furthermore, there are many methods established in organic synthesis addressing the reduction of azides to amines, but no observation of a reductive transformation of peptide azides during SPPS cleavage was yet reported. In the present study, the reduction of peptide azides...

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Novel antimicrobial peptides identified from an endoparasitic wasp cDNA library

Xiaojing Shen, Gongyin Ye, Xiongying Cheng, Chunyan Yu, more

Journal of Peptide Science > 16 > 1 > 58 - 64

We screened an endoparasitic wasp (Pteromalus puparum) cDNA library for DNA sequences having antimicrobial activity using a vital dye exclusion assay. Two dozens of clones were isolated that inhibited the growth of host Escherichia coli cells due to expression of the cloned genes. Three peptides (PP13, PP102 and PP113) were synthesized chemically based on the amino acid sequences deduced from these...

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On the use of N‐dicyclopropylmethyl aspartyl‐glycine synthone for backbone amide protection

René Röder, Petra Henklein, Hardy Weißhoff, Clemens Mügge, more

Journal of Peptide Science > 16 > 1 > 65 - 70

To prevent aspartimide formation and related side products in Asp‐Xaa, particularly Asp‐Gly‐containing peptides, usually the 2‐hydroxy‐4‐methoxybenzyl (Hmb) backbone amide protection is applied for peptide synthesis according to the Fmoc‐protocols. In the present study, the usefulness of the recently proposed acid‐labile dicyclopropylmethyl (Dcpm) protectant was analyzed. Despite the significant steric...

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COMU: A third generation of uronium‐type coupling reagents

Ayman El‐Faham, Fernando Albericio

Journal of Peptide Science > 16 > 1 > 6 - 9

COMU is a third generation of uronium‐type coupling reagent based on ethyl 2‐cyano‐2‐(hydroxyimino)acetate (Oxyma) as well as a morpholino carbon skeleton. The presence of the morpholino group has a marked influence on the solubility, stability and reactivity of the reagent. COMU performed extremely well in the presence of only 1 equiv. of base, thereby confirming the effect of the hydrogen bond acceptor...

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Colostrum and bioactive, colostral peptides differentially modulate the innate immune response of intestinal epithelial cells

Ann Louise Worsøe Jørgensen, Helle Risdahl Juul‐Madsen, Jan Stagsted

Journal of Peptide Science > 16 > 1 > 21 - 30

Characterization and identification of peptides with bioactivity from food have received considerable interest recently since such bioactive components must be adequately documented if they are part of functional food claims. We have characterized peptides from colostrum or those generated by a simulated gastrointestinal digest (GI) and tested them for bioactivity using murine intestinal (mIC_c12)...

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Novel analogues of arginine vasopressin containing α‐2‐indanylglycine enantiomers in position 2

Anna Kwiatkowska, Małgorzta Śleszyńska, Izabela Derdowska, Adam Prahl, more

Journal of Peptide Science > 16 > 1 > 15 - 20

Continuing our efforts to obtain potent and selective analogues of AVP we synthesized and pharmacologically evaluated ten new compounds modified at position 2 with α‐2‐indanylglycine or its D‐enantiomer (Igl or D‐Igl, respectively). All the peptides were tested for pressor, antidiuretic, and in vitro uterotonic activities. We also determined the binding affinity of these compounds to human OT receptor...

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Identification of a novel antitumor peptide based on the screening of an Ala‐library derived from the LALF_32–51 region

Maribel G. Vallespi, Julio R. Fernandez, Isis Torrens, Isbel Garcia, more

Journal of Peptide Science > 16 > 1 > 40 - 47

Novel therapeutic peptides are increasingly making their way into clinical application. The cationic and amphipathic properties of certain peptides allow them to cross biological membranes in a non‐disruptive way without apparent toxicity increasing drug bioavailability. By modifying the primary structure of the Limulus‐derived LALF_32–51 peptide we designed a novel peptide, L‐2, with antineoplastic...

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Microwave‐assisted TFA cleavage of peptides from Merrifield resin

Alicja Kluczyk, Magdalena Rudowska, Piotr Stefanowicz, Zbigniew Szewczuk

Journal of Peptide Science > 16 > 1 > 31 - 39

Microwave‐assisted (MW) reactions are of special interest to the chemical community due to faster reaction times, cleaner reactions and higher product yields. The adaptation of MW to solid phase peptide synthesis resulted in spectacular syntheses of difficult peptides. In the case of Merrifield support, used frequently in synthesis of special peptides, the conditions used in product cleavage are not...

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‘Sulfo‐click’ for ligation as well as for site‐specific conjugation with peptides, fluorophores, and metal chelators

Dirk T. S. Rijkers, Remco Merkx, Cheng‐Bin Yim, Arwin J. Brouwer, more

Journal of Peptide Science > 16 > 1 > 1 - 5

The ‘sulfo‐click’ reaction, which is a chemoselective amidation reaction involving the reaction of an aminoethane sulfonyl azide with a thio acid, encompasses a new approach for ligation and conjugation. Detailed protocols are provided for decorating biologically active peptides or dendrimers with biophysical tags, fluorescent probes, metal chelators, and small peptides by using this reaction as a...

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Cellular uptake and biological activity of peptide nucleic acids conjugated with peptides with and without cell‐penetrating ability

Yvonne Turner, Gerd Wallukat, Pille Säälik, Burkhard Wiesner, more

Journal of Peptide Science > 16 > 1 > 71 - 80

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 were assessed in parallel. Quantitation of the internalized PNA was performed by using an approach based on capillary electrophoresis with laser‐induced...

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Design, synthesis and biological activity of cell‐penetrating peptide‐modified octreotide analogs

Wenlin Xie, Jian Liu, Minghua Qiu, Jiancheng Yuan, more

Journal of Peptide Science > 16 > 2 > 105 - 109

Four novel octreotide analogs with cell‐penetrating peptides (CPPs) at the N‐terminus or C‐terminus were synthesized by a stepwise Fmoc solid‐phase synthesis strategy. The synthesized peptides were analyzed and characterized using reverse phase HPLC and MALDI‐TOF mass spectrometry. The antiproliferative activity of the analogs was tested in vitro on human gastric (SGC‐7901) and hepatocellular cancer...

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Slightly modifying pseudoproline dipeptides incorporation strategy enables solid phase synthesis of a 54 AA fragment of caveolin‐1 encompassing the intramembrane domain

Yves‐Marie Coïc, Charlotte Le Lan, Jean‐Michel Neumann, Nadège Jamin, more

Journal of Peptide Science > 16 > 2 > 98 - 104

This work contributes to highlight the benefits of pseudoproline dipeptides introduction in difficult SPPS. We show how a slight modification in the positioning choice conditioned the synthesis achievement of a 54 amino acid long caveolin‐1 peptide encompassing the intramembrane domain. Furthermore, we report a side reaction correlated with the coupling steps and generating truncated fragments with...

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Two tachykinin‐like peptides from skin secretions of Danio rerio

Xuhua Mi, Haining Yu, Peng Jia, Zhenzhou Zhang, more

Journal of Peptide Science > 16 > 2 > 81 - 84

Tachykinin perform multiple physiological functions such as smoothing muscle contraction, vasodilation, inflammation, the processing of nerve signal, neuroprotection and neurodegeneration. Two novel tachykinin‐like peptides named tachykinin‐DR1 and ‐DR2 were identified from skin secretions of Danio rerio in current work. Their amino acid sequences were determined as SKSQHFHGLM‐NH₂ and NKGEIFVGLM‐NH...

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Temperature‐dependent hemolytic activity of membrane pore‐forming peptide toxin, tolaasin

Kwang‐Hyun Cho, Hee‐Sung Wang, Young‐Kee Kim

Journal of Peptide Science > 16 > 2 > 85 - 90

Tolaasin, a pore‐forming peptide toxin produced by Pseudomonas tolaasii, causes brown blotch disease on cultivated mushrooms. Hemolysis using red blood cells was measured to evaluate the cytotoxicity of tolaasin. To investigate the mechanism of tolaasin‐induced cell disruption, we studied the effect of temperature on the hemolytic process. At 4 °C, poor binding of the tolaasin molecules to the erythrocyte...

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Nanofiber formation of amphiphilic cyclic tri‐β‐peptide

Yusuke Ishihara, Shunsaku Kimura

Journal of Peptide Science > 16 > 2 > 110 - 114

A novel amphiphilic cyclic peptide composed of two β‐glucosamino acids and one trans‐2‐aminocyclohexylcarboxylic acid was synthesized and investigated on assembly formation. The cyclic tri‐β‐peptide was self‐assembled into rodlike crystals or nanofibers depending on preparative conditions. The rodlike crystals showed a layer spacing of 4.8 Å along the long axis, and columnar spacings of 10.8 and 21...

INFONA - science communication portal

Journal of Peptide Science

Award Lectures

Posters

Young Investigator Oral Abstracts

Oral abstracts

Structure‐antigenicity of the V3 region of SIVmac envelope glycoprotein

Azide reduction during peptide cleavage from solid support—the choice of thioscavenger?

Novel antimicrobial peptides identified from an endoparasitic wasp cDNA library

On the use of N‐dicyclopropylmethyl aspartyl‐glycine synthone for backbone amide protection

COMU: A third generation of uronium‐type coupling reagents

Colostrum and bioactive, colostral peptides differentially modulate the innate immune response of intestinal epithelial cells

Novel analogues of arginine vasopressin containing α‐2‐indanylglycine enantiomers in position 2

Identification of a novel antitumor peptide based on the screening of an Ala‐library derived from the LALF_32–51 region

Microwave‐assisted TFA cleavage of peptides from Merrifield resin

‘Sulfo‐click’ for ligation as well as for site‐specific conjugation with peptides, fluorophores, and metal chelators

Cellular uptake and biological activity of peptide nucleic acids conjugated with peptides with and without cell‐penetrating ability

Design, synthesis and biological activity of cell‐penetrating peptide‐modified octreotide analogs

Slightly modifying pseudoproline dipeptides incorporation strategy enables solid phase synthesis of a 54 AA fragment of caveolin‐1 encompassing the intramembrane domain

Two tachykinin‐like peptides from skin secretions of Danio rerio

Temperature‐dependent hemolytic activity of membrane pore‐forming peptide toxin, tolaasin

Nanofiber formation of amphiphilic cyclic tri‐β‐peptide

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