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Fig. 2. Analytical HPLC of the product mixture obtained in 4h at RT during the folding atpH = 10.6 of (a) the bicyclic A-chain of RLN1 with the linear B-chain of RLN-2, (b) ofbicyclic A-chain of RLN1 with the B-region of IGF-1 and (c) of bicyclic A-region of IGF-1 with its linear B-region. A = bicyclic A-chain of RLN1, B = oxidized B-chain of RLN2,C = oxidized B-region of IGF-1, D = bicyclic A-region of IGF-1 and E = isomers of twochainIGF-1.IGF-1. These results indicate strong oxidizing properties inherent in the bicyclic A-chains.In many cases, the bicyclic A-chains of one INSL react readily with the linear B-chain ofthe other, but not with the monocyclic A-chain. For example, the B-chain of IGF-1 foldsreadily with the bicyclic A-chains of RLN2 or INSL3. However, folding of IGF-1 A-chainwith the B-chains of these peptides results in very low yields. Similarly, the formedmonooxidized A-chain reacts in some cases readily with cyclic B-chains to yield thecorresponding INSL (example IGF-1), while in other cases this reaction proceeds veryslowly. It is remarkable that the folding reactions of the A-region of IGF-1 and those of theC-A-region of IGF-1 with the IGF-1 B-chain proceed almost identical. It is also of interestthat IGF-1 folds similarly to the corresponding propeptide in mainly two isomers, but theopposite is observed for the chimeric peptides containing IGF B-chains which are obtainedas one isomer (Figure 2).In summary, bicyclic A-chains of INSL are powerful oxidizing peptides and fold withor oxidize readily B-chains of INSL independently of the individual chain. With theexception of IGF (similarly to the single chain IGF-1), the folding reactions proceedselectively giving exclusively the native INSL peptide, although a mixture of bicyclicA-chain isomers was applied in all cases, except of insulin. These oxidizing and reshufflingpotencies of the A-chains observed in >100 folding reactions indicate strongly theoxidoreductase character of the A-chain of INSL. Furthermore, the A-region of IGF-1seems to be responsible for the generation of the two isomers during the folding of the A orC-A-chain of IGF-1 with its B-chain.AcknowledgmentsWe thank CBL Patras for financial support.References1. Barlos, K.K., et. al. J. Peptide Sci. 16, 200-211 (2010).2. U.S. Patent Application No. 12/783,223, Unpublished (K. Barlos, et al.).159
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Solid Phase and Ligation Approaches to DendrimericImmunogen SynthesisWioleta Kowalczyk, Marta Monsó, Beatriz G. de la Torre, andDavid AndreuDepartment of Experimental and Health Sciences, Pompeu Fabra University, BarcelonaBiomedical Research Park, Barcelona, SpainIntroductionDendrimeric immunogens such as multiple antigenic peptides (MAPs) were introduced byTam some 25 years ago [1] and have found numerous applications in vaccine anddiagnostics research. However, despite extensive and successful use, experimental reportson MAP and similar dendrimeric constructs are often lacking in chemical detail about theirpreparation and characterization.MAPs can be synthetically approached by direct or indirect (convergent) methods. Inthe former approach the branched poly-lysine core and the epitopes displayed on it areentirely built by stepwise SPPS while the convergent approach relies on the chemicalligation (e.g. thioether) of properly functionalized peptide epitopes onto the poly-lysinecore [2]. Theoretically, the use of pre-purified components in the ligation reactions canresult in chemically more unambiguous materials than in stepwise methods, where minutebut cumulative synthetic errors (deletions, truncations, etc.) become amplified bymultimerization and may predictably lead to relatively heterogeneous immunogens.In this study two methods of MAP preparation have been evaluated: fully stepwiseSPPS and thioether ligation in solution. The pros and cons of both approaches have beeninvestigated using a well-known epitope, the N-terminal ectodomain (M2e) of influenzatype A virus M2 protein [3], a transmembrane tetrameric protein on the virus surface actingas an ion channel and consisting ofthree regions: the ectodomain, atransmembrane region and thecytoplasmic tail (Figure 1). The 24-residue M2e, a rather challengingsequence [4], and a shorter (12-residue, sM2e), more manageableFig. 1. Schematic structure of protein M2.version have been used as testepitopes.Results and DiscussionThe all-SPPS (direct) approach was used to prepare two MAPs, each with four copies ofsM2e. MAP B (Figure 2) only differed from A in the presence of 6-aminohexanoic acid(Ahx) spacer units at every branching point, a modification aimed at enhancing the overallflexibility of the construct. Both A and B were readily assembled on a Rink amideChemMatrix resin using Fmoc chemistry and double couplings throughout the entire sM2esequence. A was obtained in a 9% isolated yield and well characterized by MALDI-TOFMS (C 281 H 432 N 80 O 102 S 1 , MW= 6595.05 Da, [M+H + ] = 6596.28). A parallel process for Bled to a more easily purifiable final product in significantly better yield (16.5%,C 317 H 498 N 86 O 108 S 1 , MW = 7273.99Da, [M+H + ] = 7274.34).Fig. 2. Analytical HPLC of tetravalent MAP constructs (crude product) obtained byall-SPPS approach (wavy lines denote flexibilizing Ahx residues).160
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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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