Journal of Peptide Science

Cover image for Vol. 18 Issue 5

May 2012

Volume 18, Issue 5

Pages 283–356

  1. Research Articles

    1. Top of page
    2. Research Articles
    1. Self-assembly of short peptides composed of only aliphatic amino acids and a combination of aromatic and aliphatic amino acids (pages 283–292)

      Chilukuri Subbalakshmi, Sunkara V. Manorama and Ramakrishnan Nagaraj

      Version of Record online: 16 MAR 2012 | DOI: 10.1002/psc.2395

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      t-Butyloxycarbonyl (Boc)-protected peptide esters, composed of either only aliphatic or a combination of aliphatic and aromatic amino acids, formed highly organized structures when dried from methanol (MeOH) solutions. Removal of the Boc group resulted in the disruption of the tubular structure formation, although spherical aggregates were formed. Hydrophobic interaction is an important determinant of self-assembly.

    2. The agony of choice: how to find a suitable CPP for cargo delivery (pages 293–301)

      Judith Müller, Julia Triebus, Ines Kretzschmar, Rudolf Volkmer and Prisca Boisguerin

      Version of Record online: 24 MAR 2012 | DOI: 10.1002/psc.2396

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      The cellular CPP uptake depends on the used CPP and cell line and is highly affected by the CPP's C-terminal conformation (uptake: carboxyamidated CPPs > carboxylated CPPs). A successful delivery of the KLA peptide relies also on cell line, CPP and its C-terminus. 83 × 23 mm (300 × 300 DPI)

    3. Racemisation of N-Fmoc phenylglycine under mild microwave-SPPS and conventional stepwise SPPS conditions: attempts to develop strategies for overcoming this (pages 302–311)

      Mohamed A. Elsawy, Chandralal Hewage and Brian Walker

      Version of Record online: 26 MAR 2012 | DOI: 10.1002/psc.2398

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      We were involved in the conventional and MW-SPPS of a phenylglycine (Phg)-containing pentapeptide that showed Phg racemisation according to RP-HPLC, ESI-MS, and NMR data. Various synthetic conditions were attempted to reduce Phg racemisation level and to determine at which part of the synthetic cycle the epimerization had occurred. Finally, we succeeded to substantially limit the degree of Phg racemisation through an MW-SPPS (50 ºC, 22 Watts), utilizing DMTMM-BF4 coupling agent with NMM activator base and 20% piperidine as Fmoc-deprotect base.

    4. Native chemical ligation in dimethylformamide can be performed chemoselectively without racemization (pages 312–316)

      Marc Dittmann, Muheeb Sadek, Ralf Seidel and Martin Engelhard

      Version of Record online: 19 MAR 2012 | DOI: 10.1002/psc.2401

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      Native Chemical Ligation (NCL) in dimethylformamide can be conducted chemoselectively, without racemisation and reactions with other nucleophilic side chain groups. These results open the way for the ligation of hydrophobic peptides and ultimate for the synthesis of membrane proteins.

    5. Bidirectional solid phase synthesis of a model oligoglycine bolaamphiphile and purification by rapid self-assembly (pages 317–325)

      Venthan B. Naidoo and Marina Rautenbach

      Version of Record online: 23 MAR 2012 | DOI: 10.1002/psc.2402

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      The efficient bidirectional solid phase synthesis of the anionic bolaamphiphile, N,N′-suberoyldiglycylglycine, was complemented by purification using rapid self-assembly. The highly specific self-assembly can be compared with crystallisation and can be used as a purification method for analogous anionic peptides and bolaamphiphiles.

    6. Synthetic peptides derived from an N-terminal domain of the E2 protein of GB virus C in the study of GBV-C/HIV-1 co-infection (pages 326–335)

      Leticia Fernández, Weng C. Chan, Meritxell Egido, María J. Gómara and Isabel Haro

      Version of Record online: 22 MAR 2012 | DOI: 10.1002/psc.2403

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      The chemical modifications carried out in the GB virus C (GBV-C) E2 peptide to afford cyclic architecture do not result in either a clear improved reduction of the concentration needed to inhibit gp41 HIV-1-mediated cell–cell fusion or the diagnostic properties of the parent compound for the detection of GBV-C antibodies in HIV-1 co-infected patients. The utility of the linear version of this N-terminal domain for the development of new peptide-based immunosensor devices is reinforced.

    7. Site-specific fluorescein labeling of human insulin (pages 336–341)

      Fa Liu, Wayne D. Kohn and John P. Mayer

      Version of Record online: 26 MAR 2012 | DOI: 10.1002/psc.2405

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      Three fluorescein derivatives of human insulin (HI, 1) labeled at positions NαA1, NαB1 and NεB29 respectively, were synthesized using an N-trifluoroacetyl-based protecting group scheme.

    8. Inhibiting the color formation by gradient temperature-elevating Maillard reaction of soybean peptide-xylose system based on interaction of l-cysteine and Amadori compounds (pages 342–349)

      M.G. Huang, X.M. Zhang, K. Eric, S. Abbas, K. Hayat, P. Liu, S.Q. Xia and C.S. Jia

      Version of Record online: 22 MAR 2012 | DOI: 10.1002/psc.2406

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      The gradient temperature-elevating Maillard reaction was proposed as a novel method to control color formation by precisely controlling the addition time of l-cysteine. It was based on the mechanism of the color-inhibiting effect of l-cysteine. The l-cysteine reacts with the degradation and dehydration products of Amadori compounds (N-1-deoxy-xylulos-yl GSH) or possibly by the quenching rearrangement of Amadori products in the initial stages of the reaction.

    9. Kinetic and functional characterisation of the heparin-binding peptides from human transglutaminase 2 (pages 350–356)

      Kaupo Teesalu, Oivi Uibo, Raivo Uibo and Meeme Utt

      Version of Record online: 24 MAR 2012 | DOI: 10.1002/psc.2413

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      Based on the candidate peptide surface plasmon resonance analysis, we provided experimental data on heparin-binding sites of human transglutaminase 2, consisting of amino acid residues 202–215 and 261–274. Corresponding peptides displayed immunoreactivity with serum IgA of celiac disease patients and peptide P2 (261–274) reduced intestinal epithelial cell adhesion.