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H peptide Aa N1-4aSSDisulfide bridgereduction5 eq. Zn dust ; aq. 1% TFA sol.(peptide conc. 1mM) ; rt ; under ArH peptide Aa NAmide form 1-4bSHSH+ H +N to S acyl shifta Isolated yields. b Determined by chiral GC-MSH peptide Aa SNH 2SH5 eq. CHO-CO 2HH peptide Aa S37°C ; under ArHONSOThioester form 1-4cSETCA-peptides 1-4dFig. 2. Synthesis of SETCA-peptides. Peptides (1-4a) were reduced with zinc in acidicmedium (1% aqueous TFA) and reacted with glyoxylic acid to afford thiazolidines (1-4d).In order to evaluate their usefulness in NCL, SETCA-peptides were reacted withcysteinyl-peptide (Figure 3). Classical conditions were employed and ligated peptides wereobtained in high isolated yieldsH peptide 1 Aa SSETCA-peptidesHHONpeptide 1SOAa+HSHSH 2NMPAA ; TCEPrt ; under ArNHOpeptide 2 NH 2OCysteinyl-peptidespeptide 2 NH 2Fig. 3. SETCA-peptides are useful thioesters for NCL.SETCA-peptide Cys-peptide Yield (%) aH-ILKEPVHGY-SETCA H-CILKEPVHGV-NH2 62H-ILKEPVHGV-SETCA H-CILKEPVHGV-NH2 47a Isolated yieldsAcknowledgmentsWe thank financial support from CNRS, Région Nord-Pas-de-Calais, Institut Pasteur de Lille andCancéropôle Nord-Ouest. We acknowledge CSB platform (http://csb.ibl.fr) for technical support.References1. Dawson, P.E., Muir, T.W., Clark-Lewis, I., Kent, S.B.H. Science 266, 776 (1994).2. (a) Ollivier, N., Behr, J.-B, El-Mahdi, O., Blanpain, A., Melnyk, O. Org. Lett. 7, 2647 (2005); (b)Nakamura, K., Mori, H., Kawakami, T., Hojo, H., Nakahara, Y.; Aimoto, S. Int. J. Pep. Res.Therap. 13, 191 (2007); (c) Tsuda, S., Shigenaga, A., Bando, K., Otaka, A. Org. Lett. 11, 823(2009); (d) Kawakami, T., Aimoto, S. Tetrahedron 65, 3871 (2009).3. Erlandsson, M., Hällbrink, M. Int. J. Pept. Res. Ther. 11, 261 (2005).215
<strong>Proceedings</strong> of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Convenient Synthesis of C-Terminal Glycopeptide Conjugatesvia Click ChemistryJean-Philippe Ebran, Nabil Dendane, and Oleg Melnyk*CNRS UMR 8161, University of Lille Nord de France, Institut Pasteur de Lille, IFR 142,Institut de Biologie de Lille, 1 rue du Pr. Calmette, 59021, Lille, France ; http://csb.ibl.frIntroductionGlycoproteins are involved in many biological processes such as immune defense, cellgrowth or inflammation. Access to natural glycoproteins and glycopeptides are usuallyachieved by re<strong>com</strong>binant techniques or, by total or semisynthetic chemical ligationstrategies. Another approach relies on the assembly of glycopeptides mimetics containingunnatural linkages between the peptide and oligosaccharide moieties using chemicalligation. To that purpose, the regioselective Cu-Catalyzed Azide-Alkyne Cycloaddition(CuAAC) developed independently by Meldal [1] and Sharpless [2] proved to be a veryefficient and versatile tool. Indeed the chemoselective 1,3-dipolar cycloaddition between anorganic azide and a terminal alkyne lead to the 1,4-disubstituted triazole linkage. Previousworks [3,4] have reported the CuAAC ligation of unprotected azide carbohydrates andalkyne side chain peptides. Recently our research focused on the design of a novel access tounprotected C-terminal azide linker peptides and their application to copper catalyzedcycloaddition with oligosaccharide-based acetylenes.Results and DiscussionA new reliable and efficient approach regarding the synthesis of 3-azidopropyl-amine [5]salts is depicted herein (Figure 1). A two steps synthesis from phtalimide bromidederivative, via an azide phtalimideintermediate, afforded the expectedhydrochloride or tosylate salts with82 and 85% overall yield,respectively. Fmoc/tBu solid phaseFig. 1. Synthesis of amine-azide salts.FmocHNNOHONH1. SPPS2. Cu(OAc) 2, Pyridine,DCM, O 2, DIPEACl - + H 3NAc-I-L-K-E-P-V-Y-X-NH1 G 23N 3N 3%2 A 29 %3. TFA/H 2O/TIS 95/2.5/2.53 S 12 %4 V 14 %Fig. 2. Synthesis of C-terminal azide linkerpeptides.Ac-I-L-K-E-P-V-Y-A-NH N 3 +Ph Cu AAC ConditionsAc-I-L-K-E-P-V-Y-A-NH25 °C2 5peptide synthesis (SPPS) wascarried on 4-Fmoc hydrazinobenzoylAM resin. The aminolysiscleavage [6] from the solid supportwas achieved by oxidation withCu(II) in aerobic media usingazidopropylamine as nucleophilicamine. The released peptides weredeprotected by trifluoroacetic acidtreatment giving the correspondingC-terminal azide linker peptideswith yields from 12 to 29%NN NEntry Catalyst Solvent Time Conversion b1 10 mol % CuI5 eq DIPEADMF 20 h < 5%2 10 mol % CuSO4-5H2O100 mol % NaAscCH3CN/H2O 1:1 20 h < 1%3 10 mol % CuSO4-5H2O100 mol % NaAsctBuOH/H2O 1:1 4 h 99% (89 %) c4 5 mol % CuSO4-5H2O50 mol % NaAsctBuOH/H2O 1:1 20 h 93 %5 10 mol % CuSO4-5H2O100 mol % Cu(0)tBuOH/H2O 1:1 20 h 14 %6 10 mol % CuSO4-5H2O100 mol % NaAscH2O 20 h < 5%a Reactions were performed on 3 mM concentration of peptide with a ratio Azide to Alkyne of 1:2. bConversion determined by HPLC integration on azide consumption. c Isolated yieldFig. 3. Cu(I)-catalyzed cycloaddition optimization.Ph(Figure 2). Copperoxidative cleavagewas found to be thesuitable methodsince low yield(
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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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