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Table 1. Inhibitory activity of SFTI-1 analoguesAnaloguetrypsinK a [M -1 ]introduction of Hcy did not affect inhibitory activity and analogues 7 and 8 with the Hcy –Hcy disulfide bridge were among the most potent inhibitors of trypsin and chymotrypsin,respectively. It’s worth emphasizing that all active analogues appeared to be resistant toproteolysis.All eight SFTI-1 analogues (not shown in the Table) containing different-sizedcarbonyl ring (between 6 – 11 chemical bonds in the side-chain ring) displayed strongtrypsin inhibitory activity with the K a values ranging from (3.46±0.27) 10 8 M -1 for[Dap 3,11 ]SFTI-1 to (3.80±0.71) 10 9 M -1 determined for [Lys 3 ,Dap 11 ]SFTI-1. This clearlyshowed that such redox-stable modification of naturally occurring cyclic element of SFTI-1is well tolerated in the structure of the inhibitor and therefore can be beneficial for a designof peptidomimetic inhibitors of this family of enzymes.AcknowledgmentsThis work was supported by Ministry of Science and Higher Education (grant no. 2889/H03/2008/34).References1. Luckett, S., et al. J. Biol. Chem. 290, 525-533 (1999).2. Stawikowski, M., et al. ChemBioChem. 6, 1057-1061 (2005).3. Zuckermann, .R.N., et al. J. Am. Chem. Soc. 114, 10646-10647 (1992).4. Filip, K., et al. J. Pept. Sci. 9, 649-657 (2003).5. Łęgowska, A., et al. Bioorg. Med. Chem. 17, 3302-3307 (2009).chymotrypsinSFTI-1 wild (1.1 0.2) 10 10 (5.2 1.6) 10 6SFTI-1 (9.9 1.1) 10 9 (4.9 1.4) 10 6[Phe 5 ]SFTI-1 (2.0 0.2)×10 9[Nlys 5 ]SFTI-1 (1.4 0.7) 10 8[Nphe 5 ]SFTI-1 (3.9 0.3) 10 8[Nlys 5 ,Pen 3 ]SFTI-1 (1) (8.37 0.16) 10 3[Nlys 5 ,Pen 11 ]SFTI-1 (2) (3.64±0.35) 10 8[Nlys 5 ,Pen 3,11 ]SFTI-1 (3) (1.04 0.03) 10 4[Nphe 5 ,Pen 3 ]SFTI-1 (4) (1.15±0.03) 10 5[Nphe 5 ,Pen 11 ]SFTI-1 (5) (1.40±0.13) 10 8[Nphe 5 ,Pen 3,11 ]SFTI-1 (6) (3.11±0.09) 10 5[Hcy 3,11 ]SFTI-1 (7) (7.24±1.18) 10 9[Phe 5 ,Hcy 3,11 ]SFTI-1 (8) (7.56±1.79) 10 9[Nhcy 3,11 ]SFTI-1 (9)NA[Nlys 5 ,Nhcy 3,11 ]SFTI-1 (10)NA[Phe 5 ,Nhcy 3,11 ]SFTI-1 (11)NA[Nphe 5 ,Nhcy 3,11 ]SFTI-1 (12)NA[Phe 5 ,Nhcy 3 ]SFTI-1 (13)NA[Phe 5 ,Nhcy 11 ]SFTI-1 (14) (4.79±0.54) 10 8NA - not active473
<strong>Proceedings</strong> of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010B-Cell Epitope Mapping of Immunodominant Proteins inPemphigus Vulgaris: Prediction, Synthesis, andImmunoserological EvaluationHajnalka Szabados 1 , Szilvia Bősze 1 , Antal Blazsek 2 , Pálma Silló 2 ,Sarolta Kárpáti 2 , Ferenc Hudecz 1,3 , and Katalin Uray 11 Research Group of Peptide Chemistry, Hungarian Academy of Sciences, Eötvös LorándUniversity, Budapest, H-1117, Hungary; 2 Department of Dermato-Venereology and SkinOncology, Semmelweis University, Budapest, Hungary; 3 Institute of Chemistry,Eötvös Loránd University, Budapest, H-1117, HungaryIntroductionPemphigus vulgaris (PV) is an autoimmune, intraepithelial, blistering disease affecting theskin and mucous membranes and is mediated by circulating and tissue-bound IgG1 andIgG4 autoantibodies directed against keratinocyte cell surfaces. PV induced autoantibodiesbind to the extracellular domains of the desmosomal proteins desmoglein 1 (Dsg1) anddesmoglein 3 (Dsg3). Dsg1 and Dsg3 proteins are transmembranous <strong>com</strong>ponents ofdesmosomes, that are adhesion units specialized in conferring epidermal keratinocytecohesion and linked to intercellular molecules of the desmosomal plaque. The binding ofantibody to Dsg1 and Dsg3 may have a direct effect on desmosomal adherents or maytrigger a cellular process that results in acantholysis [1].Results and DiscussionAs antibody epitopes are located on the hydrophilic surface of proteins, and many of themat or near -turn structures, we have predicted -turns within the sequences of proteinsDsg1 [2] and Dsg3 [3] using the Chou-Fasman secondary structure prediction method [4]and performed hydrophobicity predictions by Eisenberg et al. [5]. Segments with lowprobability of -turn secondary structure (P -turn0) were dropped. We have reinforced our results using thePredictProtein website [6]. According to these results pentadecapeptides overlapping in fiveamino acid residues were synthesized in duplicates on hydroxypropylmethacrylate pinswith Fmoc/tBu chemistry [7] covering large parts of the extracellular domains of proteinsDsg1 and Dsg3. The side chain protecting groups were removed with trifluoroacetic acid inthe presence of scavengers, but the peptides remained covalently attached to the pins. Todetect the interaction between the autoantibodies and the synthetic peptides ELISAs(Enzyme Linked Immunosorbent Assay) were performed with the pin-attached peptidesusing sera obtained from five PV patients (previously diagnosed as Dsg1 or Dsg3 positive)and a healthy control.Fig. 1. Serum autoantibody binding to the pin-attached peptides within region 76-100 ofprotein Dsg1 (a) and within region 54-78 of protein Dsg3 (b).474
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Peptides 2010Tales of PeptidesProce
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Peptides 2010Tales of PeptidesProce
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IntroductionWe had the distinct hon
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Scientific programIn planning the 3
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31 st EUROPEAN PEPTIDE SYMPOSIUMSep
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published by John Wiley & Sons as a
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The Josef Rudinger AwardThis award
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Young Investigators' SymposiumThe y
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xxiv
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Design of Peptidyl-Inhibitors for G
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Synthetic Antifreeze Glycopeptide A
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Synthesis and Oxidative Folding of
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Convergent Syntheses of Huprp106-12
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Bactericidal Activity of Small Beta
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Bradykinin Analogues Acylated on Th
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Antimicrobial Activity of Small 3-(
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Interaction of Curcumin with A-Synu
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Fluorescent and Luminescent Fusion
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Cellular Expression of the Human An
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2D IR Spectroscopy of Oligopeptides
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large, non-redundant subset of prot
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The aberrantly glucosylated peptide
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Table 1. Proline cis/trans ratios o
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Table 1. Yields, UV-vis absorption
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Table 1. Purity of the targeted tri
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processes are blocked. Interestingl
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(tb4 n ,1 m )MTII(tb1 n ,4 m )MTIIF
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Fig. 2. a) Part of the 400 MHz HR-M
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Once printed, the amino acid partic
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A) PSA, few seconds73B) PSA, 45 min
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short β strands. In contrast, nume
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neg. control Cs9-Rhd MM-218Fig. 2.
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Table 1. The general structure of t
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% ID in the liver 1 h p.i.100908070
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Peptidyl phosphoranes were first re
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obtained from the same sardines and
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MccJ25 variants were produced by si
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Fig. 2. Proposed signaling mechanis
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Table 1. mCD4-HS12 antiviral activi
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Proceedings of the 31 st European P
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Subject index(S)-2-(1-adamantyl)gly
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chip 18chiral triazine condensing r
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heat stress 348helical conformation
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O-acyl isopeptide method 112obesity
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SH2-ligands 210short collagen-relat
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Author indexAboye, Teshome Leta 142
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Chi, Hongfang 480Chiche, Laurent 6C
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Geronikaki, Athina 444Gessmann, Ren
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Kostova, Kalina 528Kotzia, Georgia
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Nagata, Koji 162Nagayev, Igor Yu. 5
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Salvarese, Nicola 518Sammet, Benedi
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Vauquelin, Georges 138Veiga, Ana Sa
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