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The conformational preferences of selected Lys-containing analogues were assessed by CDand 2D-NMR techniques in aqueous, organic, and membrane-mimetic environments. Thesecompounds were found to be mostly helical under the different experimental conditionsexamined. The role played in the analogues by the markedly increased amphiphilicity (oneface is, partially or totally, positively charged) was further tested by fluorescence leakageexperiments in model membranes, protease resistance, antibacterial and antifungalactivities, cytotoxicity, and hemolysis (Figure 2).120100melittin[Lys 2,5,6,9 ]-trichogin[Lys 5,6 ]-trichogin80Hemolysis(%)604020[Lys 2,5,9 , Aib 6 ]-trichogin[Lys 9 ,Leu-OMe 11 ]-trichoginand Trichogin00 5 10 15 20 25 30 35Peptide conc. ( g/ml)Fig. 2. Hemolytic activities of the Lys-containing trichogin analogues.References1. Auvin-Guette, C., Rebuffat, S., Prigent, Y., Bodo, B. J. Am. Chem. Soc. 114, 2170-2174 (1992).2. Toniolo, C., Crisma, M., Formaggio, F., Peggion, C., Epand, R.F., Epand, R.M. Cell. Mol. Life Sci.58, 1179-1188 (2001).3. Peggion, C., Crisma, M., Epand, R.F., Epand, R.M., Toniolo, C. J. Pept. Sci. 9, 679-689 (2003).391
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Synthesis, Preferred Conformation, and Membrane Activity ofHeptaibin, a Medium-Length PeptaibioticMarta De Zotti, Barbara Biondi, Cristina Peggion, Marco Crisma,Fernando Formaggio, and Claudio TonioloICB, Padova Unit, CNR, Department of Chemistry, University of Padova,Padova, 35131, ItalyIntroductionThe medium-length peptaibiotics [1] are characterized by a primary structure of 13-15amino acid residues and include inter alia some samarosporins, stilbellins, bergofungins,and emerimicins. Despite the interesting antibiotic and antifungal properties exhibited bythese membrane-active peptides, their exact mechanism of action is still unknown. Ourcurrent aim is to investigate the relationships between their conformational properties andbioactivity.Results and DiscussionHere, we present our results on heptaibin, a 14-amino acid residue peptaibiotic, extractedfrom the culture of Emericellopsis sp. BAUA8289 and chemically characterized byIshiyama et al. ten years ago [2]. The heptaibin primary structure is as follows:Ac-Phe-(Aib) 3 -Val-Gly-Leu-(Aib) 2 -Hyp-Gln-Aib-Hyp-Aib-Phol(Ac, acetyl; Aib, -aminoisobutyric acid; Hyp, 4(R)-hydroxy-(S)-proline; Phol, the1,2-aminoalcohol (S)-phenylalaninol). The solid-phase synthesis of bergofungin D, thesequence of which is similar to that of heptaibin, has been recently reported [3].Our solid-phase synthesis of heptaibin involved the Fmoc-protection/HATUC-activation methodology. Special attention was devoted to prevent 2,5-dioxopiperazineformation, particularly when the N-terminal sequence of the growing chain is the H-Aib-Hyp- dipeptide. The final product was purified (Figure 1) and fully characterized. Adetailed conformational analysis was performed by use of FT-IR absorption, CD, 2D-NMRcombined with molecular dynamics (MD) calculations, and X-ray crystallography (thelatter technique on an N-terminal segment). Being rich (>50%) of the non-codedC -tetrasubstituted Aib residue, heptaibin is mostly helical under different experimentalconditions (Figure 2) and it is stable against the pronase E proteolytic attack. Fluorescenceleakage experiments revealed that heptaibin is a membrane-permeabilizing compound.15.8 min0 10 20 30time (min)Fig. 1. RP-HPLC profile obtained for heptaibin. Column: Vydac C 18 ; gradient: 50-100%B in 25min; eluants: A: H 2 O+0.1% TFA, B: CH 3 CN/H 2 O 9:1+0.1% TFA.392
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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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