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Table 1. Yields of peptide segments achieved by various methodsItem Peptide Yield Method1 HuPrP106-126 < 0.1% [ 2 ] [ 2 ]2 HuPrP106-126 9% [ 3 ] [ 3 ]C-terminal part3 UVVGGLG 65% A4 UAAAGAVVGGLG 10% A5 CVVGGLG 16% A6 CAAAGAVVGGLG 13% AN-terminal part7 KTNMKHMAG-SEt 9% B8 KTNMKHMAGAAAAG-SEt 11% B9 KTNMKHMAG-Mpa-OnBu 6% C10 KTNMKHMAGAAAAG-Mpa-OnBu 2% C11 KTNMKHMAG-SEt 30% D12 KTNMKHMAGAAAAG-SEt 6% DMiddle part13 CAAAG-SEt 54% D14 Thz-AAAG-SEt 52% DAcknowledgmentsThis work was supported by grant of Czech Science Foundation (GA CR) No. 203/07/1517 andResearch Project Z40550506.References1. Prusiner, S.B. PNAS U.S.A. 95, 13363-13383 (1998).2. Jobling, M., Barrow, C., White, A., Masters, C., Collins, S., Cappai, R. Lett. Pept. Sci. 6, 129-134(1999).3. Sebestik, J., Hlavacek, J., Stibor, I. Biopolymers 84, 400-407 (2006).4. Wan, Q., Danishefsky, S.J. Angew. Chem. Int. Ed. 46, 9248-9252 (2007).5. von Eggelkraut-Gottanka, R., Klose, A., Beck-Sickinger, A.G., Beyermann, M. Tetrahedron Lett.44, 3551-3554 (2003).6. Bang, D., Kent, S.B.H. Angew. Chem. Int. Ed. 43, 2534-2538 (2004).7. Sewing, A., Hilvert, D. Angew. Chem. Int. Ed. 40, 3395-3396 (2001).8. Backes, B.J., Ellman, J.A. J. Org. Chem. 64, 2322-2330 (1999).205
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Functionalized PNA Backbone Building Blocks Eligible forDiels-Alder Click Chemistry in Molecular ImagingRüdiger Pipkorn, Manfred Wießler, Waldemar Waldeck,Mario Koch, and Klaus BraunGerman Cancer Research Center, INF 280, D-69120, Heidelberg, GermanyIntroductionTherapies of cancer via “old fashioned” chemotherapeutics normally lead to undesiredadverse reactions followed by abortion of the therapy. Modern chemotherapeutics aremarked by their cell specific interaction with DNA without harming the surroundinghealthy tissue. This progress in chemotherapeutic development led to molecular therapiesdemanding molecular diagnostics [1-3]. The open questions concerning the transport ofimaging components in blood circulation, the differentiation between tumor andsurrounding healthy tissue, and the local enrichment within target tissue and target cells canbe answered as follows: Development and design of the needed molecules led to modularlybuilt, functional molecules which require not only synthesis and quality insurance, but alsoattributes like fast, specific, quantitative and irreversible ligation of these singlemodules[4]. Numerous approaches for improving the ligation of components finally led toour special “click chemistry”. Furthermore, a combination of several selectable differentligation compounds, either diagnostic compounds or therapeutic agents in one multistepreaction is possible by the Diels-Alder reaction with inverse electron demand (DAR inv ).Results and DiscussionThe synthesis of the functionalized PNA backbone for the DAR inv was carried out in thesteps as described here. The commonly used synthesis of the desired PNA building blocksis shown in Figure 1. The chemical synthesis of the “Reppe anhydride”-PNA buildingblock tetracyclo-[5.4.2 1,7 .O 2,6 .O 8,11 ]3,5-dioxo-4-aza-9,12-tridecadiene, Fmoc protected, isshown in Figure 2.Using the solidH 2NNH Cl 2+OOH 2NHNOOFmoc-Succinimidphase synthesis (SPPS)we can prepare functionalmodular PNAbackbonepolymers forcoupling different activeagents or imaging moleculesin order to reachlocal concentrations atthe desired target siteuntil now unachievable.Using the SPPS weprepared a pentamer(shown in Figure 3)harboring a PNA’s amidebackbone with an additionalcysteine attachedto the amino terminus,which in turn will becoupled later to thecysteine of a cell membrane transport facilitating peptide (CPP) permitting an efficientcellular uptake imperative for biochemical studies.This pentamer represents the corresponding reacting partner (a dienophile compound)for the DAR inv mediated ligation to pharmacologically active substances or molecules forimaging in diagnostics harbouring the diene groups. After attachment of the pentamerloaded with the functional molecules to the CPP, which facilitates the passage acrossbiological membranes the modular conjugate forms a “BioShuttle” transporter variant asexemplified in Figure 4.HNFmocFig. 1. Synthesis of the Fmoc protected PNA backbonemodule.Fig. 2. Synthesis of PNA monomer functionalized with Reppeanhydride.HNOO206
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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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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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