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0,440,400,36E 1/ 2(V vs SCE)0,320,280,240,200,161 2 3 4 5n- AibFig. 2. Redox potentials vs SCE of the Fc-CO-(Aib) n -OMe (n=1-5) peptide seriesrecorded at a 0.5 mm diameter gold disk electrode in CH 2 Cl 2 with 0.1 M nBu 4 NPF 6 assupporting electrolyte.The effect of the different orientation of the dipole moment (the latter increasing with thenumber of Aib residues in the backbone) was investigated by means of electrochemical andspectroscopic techniques. The oxidation potential dramatically depends on the dipoledirection and the number of Aib units (the latter tunes intramolecular hydrogen-bondformation) (Figures 1 and 2). Moreover, the dependence of current intensity on peptidelength was also explored. Finally, the shift and pattern of the C=O and N-H vibrations uponoxidation were used for mapping charge delocalization in the peptide chains, andestimating efficacy and time scale of intramolecular ET.References1. Karle, I.L., Balaram, P. Biochemistry 29, 6747-6756 (1990).2. Toniolo, C., Benedetti, E. Macromolecules 24, 4004-4009 (1991).585
<strong>Proceedings</strong> of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Paternò-Yang Photocyclization Reaction in Bpa/Met3 10 -Helical Peptides: Role of Spacer LengthAnna Cupani, Alessandro Moretto, Fernando Formaggio, andClaudio TonioloICB, Padova Unit, CNR, Department of Chemistry, University of Padova,Padova, 35131, ItalyIntroductionThe 3-(4-benzoylphenyl)alanyl (Bpa) residue is extensively used as a photoaffinity label,particularly for studies of intermolecular (peptide)ligand-receptor(protein) interaction,where it is believed to most frequently remove a hydrogen atom from the side chain of aMet residue followed by covalent C-C bond formation of the resulting radical pair [1,2].We are currently carrying out an extensive and detailed investigation of this Paternò-Yangintramolecular photochemical reaction in a series of backbone rigified, 3 10 -helical [3]hexapeptides of general sequences Boc-U x BU y MU z -OMe and Boc-U x MU y BU z -OMe,where B=(S)-Bpa, U=Aib, M=(S)-Met, and U x + U y + U z =4. We aim at determining theeffects induced by the spacer length (U y =0-3) on the chemical and 3D-structures of theresulting products and their ratios. We have already reported our results for the UBU 2 MUhexapeptide substrate 1 [4].1 Boc-Aib-Bpa-Aib-Aib-Met-Aib-OMe (i i+3)2 Boc-Aib-Bpa-Aib-Met-Aib-Aib-OMe (i i+2)3 Boc-Aib-Bpa-Met-Aib-Aib-Aib-OMe (i i+1)4 Boc-Aib-Met-Aib-Aib-Bpa-Aib-OMe (i i+3)2 3 4Fig. 1. FTIR absorption spectra in the N-H stretching region of hexapeptides 2, 3 and 4 inCDCl 3 solution. Peptide concentrations: 10 (A), 1 (B), 0.1 (C) mM.(ppm)% DMSO in CDCl 3% DMSO in CDCl3NH (1)7NH (2)7NH (5)6655-1 0 1 2 3 4 5 6 7 8 9 10 11 120 2 4 6 8 10 12(ppm)8NH (1)NH (2)(ppm)NH (1)NH (4)NH (3)7650 2 4 6 8 10 12% DMSO in CDCl 3586
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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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Page 581 and 582: Proceedings of the 31 st European P
Page 631: Proceedings of the 31 st European P
Page 679 and 680: Subject index(S)-2-(1-adamantyl)gly
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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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