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Fig. 1. Planetary ball-mill for thepreparation of larger quantities ofdipeptides.120The scale up of the reaction was alsoconsidered. Preliminary results are showingthat the results can be translated to about 5 gof dipeptide. For this purpose, the reaction wasperformed in a planetary ball-mill.We investigated also the kinetics of thereaction. Interestingly, and for each vibrationspeed, the profile (Figure 2) showed apparentzero-order kinetics in agreement with solidsolidstate reaction mechanism. This meansthat the reaction rate does not depend on theconcentration of the reactants.In conclusion, this solvent-free methodrepresents a new paradigm in the preparationof peptides.R 2 = 0,96710080% conv60402000 10 20 30 40 50 60 70 80Fig. 2. Kinetics profile of the reaction of Boc–Phe–NCA with HCl·H–Ala–OMe in thepresence of NaHCO 3 at a frequency of 30 Hz.minAcknowledgmentsWe thank the Fondation d’Entreprise EADS, the MENRT and the CNRS (Programme “Chimie pour ledéveloppement durable") for financial support.References1. Vlieghe, P., Lisowski, V., Martinez, J., Khrestchatisky, M. Drug Discovery Today 15, 40-56 (2010).2. Tanaka, K., Toda, F. Chem. Rev. 100, 1025-1074 (2000).3. Declerck, V., Nun, P., Martinez, J., Lamaty, F. Angew. Chem. Int. Ed. 48, 9318-9321 (2009).165
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010A Study to Assess the Cross-Reactivity of CelluloseMembrane Bound Peptides with Detection Systems:An Analysis at the Amino Acid LevelCarsten C. Mahrenholz, Victor Tapia, and Rudolf VolkmerInstitute of Medical Immunology, Charité Medical School, Berlin, GermanyContact: rve@charite.deIntroductionThe growing demand for binding assays to study protein-protein interaction can beaddressed by peptide array-based methods [1]. The SPOT technique is a widespreadpeptide-array technology, which is able to distinguish semi-quantitatively the bindingaffinities of peptides to defined protein targets within one array. The quality of an assaysystem used for probing peptide arrays depends on the well-balanced combination ofscreening and read-out methods. The former address the steady-state of analyte capture,whereas the latter provide the means of detecting captured analyte. In all cases, however,false positive results can occur when challenging a peptide array with analyte or detectingcaptured analyte with label conjugates. Little is known about the cross-reactivity ofpeptides with the detection agents. Here we describe at the amino acid level the potential of5-(and 6)-carboxytetramethylrhodamine [5(6)-TAMRA] to cross-react with individualamino acids in a peptide sequence. Peptides with different amino acid cores weresynthesized and tested for interaction with common dyes and detection systems. Furtherstudies including random peptide libraries and other influential factors, as well asadditional detection systems (fluoresceinisothiocyanate [FITC], and biotin/streptavidin) canbe found in our corresponding manuscript [2].Experimental SetupTo investigate the potential interaction of this detection system with individual aminoacids, 20 peptides of the sequence GGG[B] 5 GGG were designed. Herein, [B] 5 denotes fiverepeats of one of the 20 amino acids (for a schematic overview see Figure 1). Glycine wasused to create nonreactive regions flanking the functional core at the N- and C-termini. Thisapproach generates peptides of reasonable length for the homogeneous display of thedefined cores. The peptides were prepared via SPOT synthesis [3], with eachGGG[B] 5 GGG sequence repeated three times in columns on the peptide array.As soluble interaction partner, a peptide of the sequence Gly-Gly-Gly wassynthesized, N-terminally modified with TAMRA (label-GGG), and finally purified byHPLC. This tripeptide was usedto better meet the assay conditions,because labels are usuallychemically coupled to an analyteor a detection antibody.Peptide arrays containing thecore-motifs were incubated in situwith a label-GGG and evaluatedusing optical and fluorescentmethods. Strict conditionsincluding short incubation periodsand long-time washing procedureswere applied to ensurestringency of binding. Bindingexperiments resulted in measurablespot signal intensitiessignifying directly or indirectlycaptured label conjugate.Fig. 1. Peptide and analyte composition.166
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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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