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AB0 50 100 150Fig. 3. Yeast cells were incubated with increasing concentrations of SN1 and weredetected for fluorescence. (A) Columns chart describing the penetration level of SN1 overtime to the yeast cells; (B) Fluorescence microscopy images of the penetrated cells.To minimize proteolysis, we have designed the BP units so that their incorporation willform a stable peptomer sequence on solid support, using the “sub-monomer” procedure ofNuss, et al [2]. We used the BP units to synthesize a yeast permeable photo-affinity label,called SN1 (Figure 2). Fluorescein and biotin were incorporated into the structure of SN1,in addition to the BP unit, to enable additional validation techniques. Preliminary resultsindicate that SN1 penetrated into yeasts, as can be seen in Figure 3, and thus can be used tostudy protein-protein interactions in this system.We are now constructing a new analog with an additional functional group that bindsspecifically to a target protein and plan to use it to investigate the role of the targetedprotein in yeast proteomics.References1. Suva, L.J., Flannery, M.S., Caulfield, M.P., Findlay, D.M., Jüppner, H., Goldring, S.R., Rosenblatt,M., Chorev. M. J. Pharmacol. Exp. Ther. 283, 876 (1997).2. Nuss, J.M., Desai, M.C., Zuckermann, R.N., Singh, R., Renhowe, P.A., Goff, D.A., Chinn, J.P.,Wang, L., Dorr, H., Brown, E.G., Subramanian, S. Pure Appl. Chem. 69, 447 (1997).157
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010The Chains of Insulin-Like Peptides Reveal Properties ofOxidoreductasesKostas K. Barlos, Zoe Vasileiou, Vasso Chatziharalampous,Dimitrios Gatos, and Kleomenis BarlosDepartment of Chemistry, University of Patras, 26500, Patras, GreeceIntroductionVarious physiological and pathological conditions can lead to protein misfolding and cellstress. Protein misfolding is the originating factor of more than 60% of human diseasesincluding aging, several cancer types, Alzheimer’s disease and diabetes. Therefore, a betterunderstanding of the principles that determine folding and unfolding of peptides andproteins could facilitate the development of artificial oxidoreductases and chaperones. Wehave recently found [1] that oxidized A-chain of the insulin like-peptide (INSL) humanrelaxin-2 (RLN2) reacts with the B-chain of human relaxin giving RLN2 with the nativecharacteristic disulfide bond pattern and as a side product oxidized B-chain. It is believedthat the chains of the INSL contain the structural information required for native folding inthe sequence of their corresponding propeptides which fold correctly before the enzymaticcleavage, which results in the two chain native structure of the peptide. A question arisesfrom the common disulfide bond pattern in INSL. Is folding determined by the individualsequences of the whole propeptide chains, the sequences of the A- and B-regions/chains orthe distribution pattern of the sulphur atoms within the chains? In the latter case, folding ofthe A- and B-chains originating from different INSL could be also possible. If so, INSLcould become easily accessible synthetically, as well as chimeric INSL.Results and DiscussionThe A and B-chains of the INSL (Figure 1) were synthesized by SPPS utilizing Fmocaminoacids and 2-chlorotrityl resin. Chains containing Met were also synthesized as thecorresponding Met-sulfoxide derivatives. The linear peptides were purified by preparativeHPLC and the A-chains were oxidized with DMSO to the corresponding two disulfidebonds containing bicyclic derivatives. In all cases we obtained bicyclic A-chain as amixture of the expected three bicyclic isomers with the remarkable exception of insulinA-chainRelaxin 1 RPYVALFEKCCLI GCTKRSLAKYCRelaxin 2 ZLYSALANKCCHVGCTKRSLARFCRelaxin 3 DVLAGLSSSCCKWGCSKSEISSLCInsulinGIVEQCCTSI CSLYQLENYCNIGF-1 APQTGIVDECCFRSCDLRRLEMYCAIGF-2 RRSRGIVEECCFRSCDLALLETLCAINSL 3 AAATNPARYCCLSGCTQQDLLTLCPYINSL 4 RSGRHRFDPFCCEVI CDDGTSVKLCINSL 5 QDLQTLCCTDGCSMTDLSALCINSL 6GYSEKCCLTGCTKEELSIACB-chainRelaxin 1 KWKDDVIKLCGRELVRAQ IAICGMSTWSRelaxin 2 DSWMEEVIKLCGRELVRAQ IAICGMSTWSRelaxin 3 RAAPYGVRLCGREFIRAVI FTCGGRWInsulinVNQHLCGSHLVEALYLVCGERGFFYTPKAIGF-1GPETLCGAELVDALQFVCGDRGFYFNKPIGF-2PSETLCGGELVDTLQFVCGDRGFYFSRPINSL 3 PTPEMREKLCGHHFVRALVRVCGGPRWSTEAINSL 4 ZSLAAELRGCGPRFGKHLLSYCPMPEKTFTTTPINSL 5 SKESVRLCGLEY IRTV I Y I CASSRWINSL 6 SDISSARKLCGRYLVKE I EKLCGHANWSFRCA-chainIGF-1GYGSSSRRAPQTAPQTGIVDECCFRSCDLALLETLCAFig. 1. Sequences of INSL; with bold areindicated conserved or almost conservedresidues.where exclusively one bicyclic A-chainisomer is formed. Excess (1.05-4.00mmolar) of bicyclic A-chain was thenreacted with the linear B-chain of INSL[2]. The reactions were performed underdenaturing conditions (Gnd.HCl) at pH= 10.6 (Na-glycinate) in the presence ofthe mild oxidant DMSO (5-50%). Theproceeding of the reaction was followedby LC-MS.In all cases mainly three productsare obtained in various ratios. INSL,oxidized B-chain and dimeric chain-B.Linear chain-B is consumed in all casesalmost quantitatively within 5 min at RTif the excess of bicyclic A-chain overlinear B-chain is equal or exceeds the2:1 ratio. Under these conditions B-chains were converted to INSL in 2-65% yield. Low yields were observed inthe case of insulin (high yield of insulinis obtained if bicyclic A-chain andcyclic B-chain are equilibrated in thepresence of a thiol catalyst) and RLN3.The highest yields were obtained in thecase of RLN1, RLN2, INSL3 and158
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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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