Journal of Peptide Science

Cover image for Vol. 20 Issue 3

March 2014

Volume 20, Issue 3

Pages i–iii, 159–234

  1. Issue Information

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

      Version of Record online: 11 FEB 2014 | DOI: 10.1002/psc.2558

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  2. Research Articles

    1. Top of page
    2. Issue Information
    3. Research Articles
    1. Isolation and characterization of SsmTx-I, a Specific Kv2.1 blocker from the venom of the centipede Scolopendra Subspinipes Mutilans L. Koch (pages 159–164)

      Minzhi Chen, Jing Li, Fan Zhang and Zhonghua Liu

      Version of Record online: 27 JAN 2014 | DOI: 10.1002/psc.2588

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      SsmTx-I, a novel peptide toxin from the venom of the centipede S subspinipes mutilans, specifically inhibits voltage-gated K+ channel subtype Kv2.1.

    2. Insight into the structures of the second and fifth transmembrane domains of Slc11a1 in membrane mimics (pages 165–172)

      Li Wang, Dan Wang and Fei Li

      Version of Record online: 22 JAN 2014 | DOI: 10.1002/psc.2593

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      The second transmembrane domain TMD2 of Slc11a1 was revealed to adopt an α-helical structure in membrane-mimic environment. The fifth transmembrane domain TMD5 of Slc11a1 was found to form an α-helix with a less space-occupied face, and the α-helix is partially unfolded in the N-terminal region when Gly197 is substituted by Val.

    3. Cyclo(d-Tyr-d-Phe): a new antibacterial, anticancer, and antioxidant cyclic dipeptide from Bacillus sp. N strain associated with a rhabditid entomopathogenic nematode (pages 173–185)

      S. Nishanth Kumar, C. Dileep, C. Mohandas, Bala Nambisan and Jayaprakas Ca

      Version of Record online: 19 DEC 2013 | DOI: 10.1002/psc.2594

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      A new microbial cyclic dipeptide (diketopiperazine), cyclo(D-Tyr-D-Phe) was isolated for the first time from the ethyl acetate extract of fermented modified nutrient broth of Bacillus sp. N strain associated with rhabditid entomopathogenic nematode. The antibacterial, anticancer and antioxidant activity of cyclo(d-Tyr-d-Phe) is also reported for the first time. We also compared the biological activity of natural cyclo(d-Tyr-d-Phe) with synthetic cyclo(d-Tyr-D-Phe) and cyclo(L-Tyr-L-Phe). Natural and synthetic cyclo(d-Tyr-d-Phe) recorded similar pattern of activity, whereas synthetic cyclo(L-Tyr-L-Phe) recorded lower activity. This clearly indicated that stereochemistry plays an important role in the bioactivity of cyclic dipeptides.

    4. An important side reaction using the thiol, 3,6-dioxa-1,8-octanedithiol (DODT), in 9-fluorenylmethoxycarbonyl-based solid phase peptide synthesis (pages 186–190)

      Paul W. R. Harris, Renata Kowalczyk, Sung-Hyun Yang, Geoffrey M. Williams and Margaret A. Brimble

      Version of Record online: 18 DEC 2013 | DOI: 10.1002/psc.2595

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      We outline a novel alkylation when using the dithiol 3,6-dioxa-1,8-octanedithiol (DODT) as a scavenger in TFA-mediated peptide cleavage from the resin. Peptides containing unprotected methionine were extensively modified by a DODT-derived alkylating agent affording a previously unreported by-product. Conditions for the prevention or subsequent removal of the by-product are outlined.

    5. The 4-pyridylmethyl ester as a protecting group for glutamic and aspartic acids: ‘flipping’ peptide charge states for characterization by positive ion mode ESI-MS (pages 191–195)

      Sriramya Garapati and Colin S. Burns

      Version of Record online: 21 JAN 2014 | DOI: 10.1002/psc.2598

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      Side-chain protection of glutamic and aspartic acid residues by the 4-pyridylmethyl ester group enables the charge state of a peptide to be switched from negative to positive, thus making detection by positive ion mode ESI-MS possible. This protecting group is useful in the synthesis of highly acidic peptide sequences, which are often beset by problems with purification by standard RP HPLC and characterization by ESI-MS.

    6. Screening and identification of a specific peptide binding to hepatocellular carcinoma cells from a phage display peptide library (pages 196–202)

      Yonge Guo, Caixia Ma, Chunyan Li, Jinling Wu, Dan Zhang, Juanjuan Han, Qixuan Wang, Jinhui Xu, Shaoying Lu and Yingchun Hou

      Version of Record online: 30 JAN 2014 | DOI: 10.1002/psc.2599

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      The specific binding to HepG2 cells indicates that HCSP4-fluorescein isothiocyanate (FITC) may be a promising lead candidate for molecular imaging and targeted drug delivery in the diagnosis and therapy of hepatocellular carcinoma. A, B: HCSP4-FITC binds to HepG2 cells specifically; C, D: the nuclei (C) and membrane (D) of HepG2 cells are displayed using DAPI and Dil staining methods; E, F: the merged photos show that HCSP4-FITC binds to the surfaces of HepG2 cells specifically.

    7. Solvent effects on the conformational preferences of model peptoids. MP2 study (pages 203–211)

      Roksana Wałęsa and Małgorzata A. Broda

      Version of Record online: 21 JAN 2014 | DOI: 10.1002/psc.2601

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      The influence of water on peptoid conformational properties was studied by PCM/MP2 method. The theoretical calculations show that aqueous environment increases the tendency of methylated peptide bond to adopt the cis configuration and distinctly stabilizes conformers with torsion angles corresponding to polyproline helices PPII and PPI.

    8. Synthetic peptide octarphin (TPLVTLFK), a selective agonist of nonopioid β-endorphin receptor, stimulates nitric oxide synthesis in macrophages (pages 212–215)

      Vladimir B. Sadovnikov and Elena V. Navolotskaya

      Version of Record online: 8 JAN 2014 | DOI: 10.1002/psc.2603

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      Synthetic peptide octarphin (TPLVTLFK, a selective agonist of nonopioid beta-endorphin receptor) was able to activate in a dose-dependent manner murine macrophages to express nitric oxide (NO) synthase and to produce NO.

    9. A rapid procedure to isolate isotopically labeled peptides for NMR studies: application to the Disabled-2 sulfatide-binding motif (pages 216–222)

      Shuyan Xiao, Xiaolin Zhao, Carla V. Finkielstein and Daniel G. S. Capelluto

      Version of Record online: 27 JAN 2014 | DOI: 10.1002/psc.2604

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      Recombinant Disabled-2 sulfatide-binding motif (SBM) can be efficiently isolated in an intact and active form for NMR studies. The reported approach can be easily applied to the isolation of recombinant peptides for structural studies. The figure displays 1H, 15N-HSQC overlaid spectra of 15N-labeled Disabled-2 SBM in the absence (red) and presence of dodecylphosphocholine micelles (black). Addition of micelles improved resolution of the spectrum of the peptide, suggesting that this region is responsible for Disabled-2 membrane targeting.

    10. Nanostructures from the self-assembly of α-helical peptide amphiphiles (pages 223–228)

      Qingbin Meng, Yingying Kou, Xin Ma, Lei Guo and Keliang Liu

      Version of Record online: 30 JAN 2014 | DOI: 10.1002/psc.2606

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      We designed a series of four peptide amphiphiles (PAs) with varied heptad repeated peptide headgroup lengths. As the number of heptad repeats in the PAs increased, the secondary structures of the PAs tended to display α-helical conformations, and the nanostructure of the self-assembled peptides changed from nanofibers to nanovesicles. This research provides a useful way of modulating the self-assembly of α-helical PAs.

    11. A naturally occurring αs1-casein-derived peptide in bovine milk inhibits apoptosis of granulosa cells induced by serum-free conditions (pages 229–234)

      T. Shimizu, K. Ganzorig, A. Miyamoto, T. Ishii, T. Urashima and K. Fukuda

      Version of Record online: 8 JAN 2014 | DOI: 10.1002/psc.2609

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      An αs1-casein derived peptide, αs1-CN (f16-23) (RPKHPIKH), was found in bovine raw milk. Its chemically synthesized peptide inhibited apoptosis of bovine granulosa cells induced by serum-free conditions in a dose-dependent manner.

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