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1. |
O‐Acyl isopeptide method: development of anO‐acyl isodipeptide unit for BocSPPSand its application to the synthesis of Aβ1‐42 isopeptide |
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Journal of Peptide Science,
Volume 20,
Issue 9,
2014,
Page 669-674
Taku Yoshiya,
Tsuyoshi Uemura,
Takahiro Maruno,
Shigeru Kubo,
Yoshiaki Kiso,
Youhei Sohma,
Yuji Kobayashi,
Kumiko Yoshizawa‐Kumagaye,
Yuji Nishiuchi,
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摘要:
TheO‐acyl isopeptide method was developed for the efficient preparation of difficult sequence‐containing peptide. Furthermore, development of theO‐acyl isodipeptide unit for Fmoc chemistry simplified its synthetic procedure by solid‐phase peptide synthesis. Here, we report a novel isodipeptide unit for Boc chemistry, and the unit was successfully applied to the synthesis of amyloidβpeptide. Combination of Boc chemistry and the isodipeptide unit would be an effective method for the synthesis of many difficult peptides. Copyright © 2014 European Peptide Society and John Wiley&
ISSN:1075-2617
DOI:10.1002/psc.2662
年代:2014
数据来源: WILEY
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2. |
Matrix‐assisted peptide synthesis on nanoparticles |
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Journal of Peptide Science,
Volume 20,
Issue 9,
2014,
Page 675-679
Raz Khandadash,
Victoria Machtey,
Aryeh Weiss,
Gerardo Byk,
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摘要:
We report a new method for multistep peptide synthesis on polymeric nanoparticles of differing sizes. Polymeric nanoparticles were functionalized via their temporary embedment into a magnetic inorganic matrix that allows multistep peptide synthesis. The matrix is removed at the end of the process for obtaining nanoparticles functionalized with peptides. The matrix‐assisted synthesis on nanoparticles was proved by generating various biologically relevant peptides. Copyright © 2014 European Peptide Society and John Wiley&Sons, L
ISSN:1075-2617
DOI:10.1002/psc.2664
年代:2014
数据来源: WILEY
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3. |
Molecular characterization of a novel hepcidin (HepcD) fromCamelus dromedarius. Synthetic peptide forms exhibit antibacterial activity |
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Journal of Peptide Science,
Volume 20,
Issue 9,
2014,
Page 680-688
Mohamed Boumaiza,
Aymen Ezzine,
Maryse Jaouen,
Marie‐Agnes Sari,
Mohamed Nejib Marzouki,
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摘要:
Hepcidin is a cysteine‐rich peptide widely characterized in immunological processes and antimicrobial activity in several vertebrate species. Obviously, this hormone plays a central role in the regulation of systemic iron homeostasis. However, its role in camelids' immune response and whether it is involved in antibacterial immunity have not yet been proven. In this study, we characterized the Arabian camel hepcidin nucleotide sequence with an open reading frame of 252 bp encoding an 83‐amino acid preprohepcidin peptide. Eight cysteine key residues conserved in all mammalian hepcidin sequences were identified. The model structure analysis of hepcidin‐25 peptide showed a high homology structure and sequence identity to the human hepcidin. Two different hepcidin‐25 analogs manually synthesized by SPPS shared significant cytotoxic capacity toward the Gram‐negative bacteriumEscherichia coliAmerican Type Culture Collection (ATCC) 8739 as well as the Gram‐positive bacteriaBacillus subtilisATCC 11779 andStaphylococcus aureusATCC 6538in vitro. The three disulfide bridges hepcidin analog demonstrated bactericidal activity, againstB. subtilisATCC 11779 andS. aureusATCC 6538 strains, at the concentration of 15 μM (50 µg/ml) or above at pH 6.2. This result correlates with the revealed structural features suggesting that camel hepcidin is proposed to be involved in antibacterial process of innate immune response. Copyright © 2014 European Peptide Societ
ISSN:1075-2617
DOI:10.1002/psc.2644
年代:2014
数据来源: WILEY
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4. |
Epitope mapping of the N‐terminal portion of tissue transglutaminase protein antigen to identify linear epitopes in celiac disease |
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Journal of Peptide Science,
Volume 20,
Issue 9,
2014,
Page 689-695
Margherita Di Pisa,
Patrick Buccato,
Giuseppina Sabatino,
Feliciana Real Fernández,
Brunilde Berti,
Francesco Cocola,
Anna Maria Papini,
Paolo Rovero,
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摘要:
Celiac disease (CD) is an autoimmune mediated disease with complex and multifactorial etiology. Gluten intake triggers a composite immune response involving T‐cells and B‐cells and leading to the secretion of autoantibodies if a genetic predisposition is present. Untreated CD patients show high levels of circulating autoantibodies directed to different auto‐antigens present in the intestinal mucosa. The most important auto‐antigen is the endomysial enzyme tissue transglutaminase (tTG). Both IgA and IgG antibody isotypes to tTG are known, but only the IgA antibodies demonstrate the highest disease specificity and thus are considered disease biomarkers. Because the pathogenicity and exact tTG binding properties of these autoantibodies are still unclear, the characterization of tTG antigenic domains is a crucial step in understanding CD onset and the autoimmune pathogenesis. Overlapping peptide libraries can be used for epitope mapping of selected protein portions to determine antigenic fragments contributing to the immunological activity and possibly develop innovative peptide‐based tools with high specificity and sensitivity for CD. We performed an epitope mapping study to characterize putative linear auto‐antigenic epitopes present in the tTG N‐terminal portion (1–230). A library of 23 overlapping peptides spanning tTG(1–230) was generated by Fmoc/tBu solid‐phase peptide synthesis and screened by immunoenzymatic assays employing patients' sera. The results indicate that four synthetic peptides, that is, Ac‐tTG(1–15)‐NH2, Ac‐tTG(41–55)‐NH2, Ac‐tTG(51–65)‐NH2, and Ac‐tTG(151–165)‐NH2, are recognized by IgA autoantibodies circulating in CD patients' sera. These results offer important insight on the nature of the antigen‐antibody interaction. Copyright © 2014 Eur
ISSN:1075-2617
DOI:10.1002/psc.2650
年代:2014
数据来源: WILEY
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5. |
‘Click’ chemistry synthesis and capillary electrophoresis study of 1,4‐linked 1,2,3‐triazole AZT‐systemin conjugate |
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Journal of Peptide Science,
Volume 20,
Issue 9,
2014,
Page 696-703
Michał Dobkowski,
Aleksandra Szychowska,
Małgorzata Pieszko,
Anna Miszka,
Monika Wojciechowska,
Magdalena Alenowicz,
Jarosław Ruczyński,
Piotr Rekowski,
Lech Celewicz,
Jan Barciszewski,
Piotr Mucha,
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摘要:
The Cu(I) catalyzed Huisgen 1,3‐dipolar azide‐alkyne cycloaddition (CuAAC) was applied for a nucleoside‐peptide bioconjugation. Systemin (Sys), an 18‐aa plant signaling peptide naturally produced in response to wounding or pathogen attack, was chemically synthesized as itsN‐propynoic acid functionalized analog (Prp‐Sys) using the SPPS. Next, CuAAC was applied to conjugate Prp‐Sys with 3′‐azido‐2′,3′‐dideoxythymidine (AZT), a model cargo molecule. 1,4‐Linked 1,2,3‐triazole AZT‐Sys conjugate was designed to characterize the spreading properties and ability to translocate of cargo molecules of systemin. CuAAC allowed the synthesis of the conjugate in a chemoselective and regioselective manner, with high purity and yield. The presence of Cu(I) ions generatedin situdrove the CuAAC reaction to completion within a few minutes without any by‐products. Under typical separation conditions of phosphate ‘buffer’ at low pH and uncoated fused bare‐silica capillary, an increasing peak intensity assigned to triazole‐linked AZT‐Sys conjugate was observed using capillary electrophoresis (CE) during CuAAC. CE analysis showed that systemin peptides are stable in tomato leaf extract for up to a few hours. CE‐ESI‐MS revealed that the native Sys and its conjugate with AZT are translocated through the tomato stem and can be directly detected in stem exudates. The results show potential application of systemin as a transporter of low molecular weight cargo molecules in tomato plant and of CE method to characterize a behavior of plant peptides and its analogs. Copyright © 2014 E
ISSN:1075-2617
DOI:10.1002/psc.2653
年代:2014
数据来源: WILEY
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6. |
Captides: rigid junctions between beta sheets and small molecules |
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Journal of Peptide Science,
Volume 20,
Issue 9,
2014,
Page 704-715
Brandon L. Kier,
Niels H. Andersen,
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摘要:
An extensive series of covalently linked small molecule–peptide adducts based on a terminally capped‐beta hairpin motif is reported. The constructs can be prepared by standard solid‐phase Fmoc chemistry with one to four peptide chains linked to small molecule hubs bearing carboxylic acid moieties. The key feature of interest is the precise, buried environment of the small molecule, and its rigid orientation relative to one or more short but fully structured peptide chain(s). Most of this study employs a minimalist nine residue ‘captide’, a cappedβ‐turn, but we illustrate general applicability to peptides which can terminate in a beta strand. The non‐peptide portion of these adducts can include nearly any molecule bearing one or more carboxylic acid groups. Fold‐dependent rigidity sets this strategy apart from the currently available bioconjugation methods, which typically engender significant flexibility between peptide and tag. Applications to catalyst enhancement, drug design, higher‐order assembly, and FRET calibration rulers are discussed. Copyright © 2014 European Peptide Society and J
ISSN:1075-2617
DOI:10.1002/psc.2657
年代:2014
数据来源: WILEY
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7. |
Inhibitory effect of the carnosine–gallic acid synthetic peptide on MMP‐2 and MMP‐9 in human fibrosarcoma HT1080 cells |
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Journal of Peptide Science,
Volume 20,
Issue 9,
2014,
Page 716-724
Sung‐Rae Kim,
Tae‐Kil Eom,
Hee‐Guk Byun,
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摘要:
Matrix metalloproteinases (MMPs) are a family of zinc‐dependent endopeptidases that degrade extracellular matrix components and play important roles in a variety of biological and pathological processes such as malignant tumor metastasis and invasion. In this study, we constructed carnosine–gallic acid peptide (CGP) to identify a better MMP inhibitor than carnosine. The inhibitory effects of CGP on MMP‐2 and MMP‐9 were investigated in the human fibrosarcoma (HT1080) cell line. As a result, CGP significantly decreased MMP‐2 and MMP‐9 expression levels without a cytotoxic effect. Moreover, CGP may inhibit migration and invasion in HT1080 cells through the urokinase plasminogen activator (uPA)–uPA receptor signaling pathways to inhibit MMP‐2 and MMP‐9. Based on these results, it appears that CGP may play an important role in preventing and treating several MMP‐2 and MMP‐9‐mediated health problems such as metastasis. Copyright © 2014 European Peptide Society
ISSN:1075-2617
DOI:10.1002/psc.2658
年代:2014
数据来源: WILEY
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8. |
Synthesis of lucifensin by native chemical ligation and characteristics of its isomer having different disulfide bridge pattern |
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Journal of Peptide Science,
Volume 20,
Issue 9,
2014,
Page 725-735
Stancho Stanchev,
Zbigniew Zawada,
Lenka Monincová,
Lucie Bednárová,
Jiřina Slaninová,
Vladimír Fučík,
Václav Čeřovský,
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摘要:
The antimicrobial 40‐amino‐acid‐peptide lucifensin was synthesized by native chemical ligation (NCL) usingN‐acylbenzimidazolinone (Nbz) as a linker group. NCL is a method in which a peptide bond between two discreet peptide chains is created. This method has been applied to the synthesis of long peptides and proteins when solid‐phase synthesis is imcompatible. Two models of ligation were developed: [15 + 25] Ala‐Cys and [19 + 21]His‐Cys. The [19 + 21] His‐Cys method gives lower yield because of the lower stability of 18‐peptide‐His‐Nbz‐CONH2peptide, as suggested by density functional theory calculation. Acetamidomethyl‐deprotection and subsequent oxidation of the ligated linear lucifensin gave a mixture of lucifensin isomers, which differed in the location of their disulfide bridges only. The dominant isomer showed unnatural pairing of cysteines [C1−6], [C3−5], and [C2−4], which limits its ability to formα‐helical structure. The activity of isomeric lucifensin towardBacillus subtilis,Staphylococcus aureus, andMicrococcus luteuswas lower than that of the natural lucifensin. The desired product native lucifensin was prepared from this isomer using a one‐pot reduction with dithiotreitol and subsequent air oxidation in slightly alkaline medium. Copyright © 2014
ISSN:1075-2617
DOI:10.1002/psc.2663
年代:2014
数据来源: WILEY
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9. |
Synthesis, characterization, and biological activity of poly(arginine)‐derived cancer‐targeting peptides in HepG2 liver cancer cells |
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Journal of Peptide Science,
Volume 20,
Issue 9,
2014,
Page 736-745
Stesha C. Joseph,
Brittany A. Blackman,
Megan L. Kelly,
Mariana Phillips,
Michael W. Beaury,
Ivonne Martinez,
Christopher J. Parronchi,
Constantine Bitsaktsis,
Allan D. Blake,
David Sabatino,
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摘要:
The solid‐phase synthesis, structural characterization, and biological evaluation of a small library of cancer‐targeting peptides have been determined in HepG2 hepatoblastoma cells. These peptides are based on the highly specific Pep42 motif, which has been shown to target the glucose‐regulated protein 78 receptors overexpressed and exclusively localized on the cell surface of tumors. In this study, Pep42 was designed to contain varying lengths (3–12) of poly(arginine) sequences to assess their influence on peptide structure and biology. Peptides were effectively synthesized by 9‐fluorenylmethoxycarbonyl‐based solid‐phase peptide synthesis, in which the use of a poly(ethylene glycol) resin provided good yields (14–46%) and crude purities>95% as analyzed by liquid chromatography–mass spectrometry. Peptide structure and biophysical properties were investigated using circular dichroism spectroscopy. Interestingly, peptides displayed secondary structures that were contingent on solvent and length of the poly(arginine) sequences. Peptides exhibited helical and turn conformations, while retaining significant thermal stability. Structure–activity relationship studies conducted by flow cytometry and confocal microscopy revealed that the poly(arginine) derived Pep42 sequences maintained glucose‐regulated protein 78 binding on HepG2 cells while exhibiting cell translocation activity that was contingent on the length of the poly(arginine) strand. In single dose (0.15 mM) and dose‐response (0–1.5 mM) cell viability assays, peptides were found to be nontoxic in human HepG2 liver cancer cells, illustrating their potential as safe cancer‐targeting delivery agents. Copyright © 2014 European Peptide
ISSN:1075-2617
DOI:10.1002/psc.2665
年代:2014
数据来源: WILEY
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10. |
Issue information |
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Journal of Peptide Science,
Volume 20,
Issue 9,
2014,
Page -
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PDF (411KB)
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ISSN:1075-2617
DOI:10.1002/psc.2564
年代:2014
数据来源: WILEY
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