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Solid-phase synthesis on the 2-Cl-Trt resin was performed by Fmoc-/t-Bu strategy bothusing standard methods of the sequential chain elongation and in a convergent manner [5],the corresponding fragments selection is marked in the table by the || sign.DIC, HOBt, HOAt, and PyBOP served as condensing agents, reactions were run inDMF and NMP. The conversion of reactions was estimated using the Kaiser test andbromophenol blue.The purification of the compounds obtained was carried out via preparative reversedphaseHPLC. Their purity turned to be not less than 95%. The molecular ion peaks inmass-spectra MALDI-TOF were in accordance with calculated peaks for all synthesizedpeptides.At the moment the peptides under discussion are undergoing biological tests on thebase of the Research Institute of Influenza situated in Saint-Petersburg.References1. De Clercq, E. Nature Rev. Microbiol. 2, 704-720 (2004).2. Kiselev, O.I., Deeva, E.G., Slita, A.V., Platonov, V.G. Anti-viral medications for influenza andacute respiratory disease therapy. Drug design based on polymer carriers. Publishing house ofInformation and Analysis Center “Vremya”, St-Petersburg, 2000, p.132. (Published in Russian).3. Trivedi, V.D., Cheng, S.-F., Wu, C.-W., Karthikeyan, R., Chen, C.-J., Chang, D.-K. ProteinEngineering 16, 4, 311-317 (2003).4. Ghanem, A., Mayer, D., Chase, G., Tegge, W.F., Ronald, K.G., García-Sastre, A., Schwemmle, M.Journal of Virology 81, 14, 7801-7804 (2007).5. Chan, W.C., White, P.D. Fmoc solid phase peptide synthesis, Oxford University press, 2004.549
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010The Adjuvant Activity of Glucosaminyl Muramyl Dipeptide(GMDP) is Linked to the Beta-Anomer Configuration andN-Acetylglucosamine (GlcNac) Uptake SystemElena A. Meshcheryakova, Elena P. Dobrushkina,Tatiana M. Andronova, and Vadim T. IvanovShemyakin-Ovchinnikov Institute of Bioorganic Chemistry RAS, Moscow, 117997,Russian FederationIntroductionGlucosaminyl muramyl dipeptide (GMDP, Figure 1) is the minimum unit of bacterial cellwall peptidoglycan which is the most potent activator of mammalian innate immunesystem. Numerous biological activities of GMDP including adjuvanticity, make it attractivefor medical practice and GMDP has been used successfully in Russian Federation as themedicine Licopid ® during more than ten years.Recently it has been revealed that GMDP stimulates the innate immunity viaactivation of NF-kB signal pathway by means of intracellular NOD2 receptor [1], but theway by which this glycopeptide penetrates the cell and conformational requirements of thisprocess are poorly understood. In this work we studied the influence of alfa-, beta-anomersequilibrium of GMDP molecule on their adjuvant activity. Besides, in order to highlight themechanism of GMDP uptake we measured the GMDP adjuvant activity in the presence ofGly-Sar (agonist peptide transporter PEPT1) and N-acetylglucosamine (GlcNac) whichmodels the terminal unit of GMDP.We found that only beta-conformer of GMDP stimulates adjuvant activity and onlyGlcNac but not Gly-Sar competed with GMDP during uptake process.Results and DiscussionFig. 1. GMDP anomer equilibrium.Isolation of GMDP samples with 82% betaanomerand 95% alfa-anomer.The possibility to isolate GMDP fractionswith 82% beta-anomer strongly depended on theinjected quantity of GMDP to the preparativecolumn (reversed phase column 100x600 mm,filled by sorbent Polygoprep 100-30, C18(Macherey-Nagel). When injected quantity ofGMDP was 46 g, the zone 5 on chromatogramwas absent, but a little excess up to 50 g causedthe appearance of zone 5 which contained 82%beta-anomer of GMDP (Figure 2A). 95% alfaanomerof GMDP was collected at 36 min (zone6, Figure 2A) of preparative chromatographicprocess. Figures 2B and C demonstrate theanalytical chromatograms of isolated 82% betaanomerand 95% alfa-anomer of GMDP.Fig. 2. Preparative (left) and analytical (middle, right) HPLC chromatograms.550
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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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