Peptides 2010 Tales of Peptides Proceedings of the Thirty-First European Peptide Symposium September 5-9, 2010, Copenhagen, Denmark Edited by Michal Lebl Prompt Scientific Publishing, San Diego, CA, USA michallebl@gmail. com Morten Meldal Carlsberg Laboratory, Copenhagen, Denmark [email protected]Knud J. Jensen University of Copenhagen, Faculty of Life Sciences, Denmark [email protected]Thomas Heeg-Jensen Novo Nordisk A/S, Maaloev, Denmark tshj@novonordisk. com European Peptide
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Peptides 2010
Tales ofPeptides
Proceedings of the Thirty-First
European Peptide SymposiumSeptember 5-9, 2010, Copenhagen, Denmark
N-Pi Interactions in the Molecules of Life 2Amit Choadhary, Ronald T, Raines
Mimicry Effect ofthe Neo-Epitope [Asn641(Glc)]FAN(635-655) withCSF114(Glc) Detecting Autoantibodies in Multiple Sclerosis 4Shashank Pandey, Elisa Peroni, Maria Claudia Alcaro, Fabio Rizzolo, MarioChelli, Paolo Rovero, Francesco Lolli, Anna Maria PapiniCyclic Peptides with a Diversely Substituted Guanidine Bridge: Synthesis,Structural and Biological Evaluations of Model Peptides 6Youness Touati Jallabe, Engin Bojnik, Laurent Chiche, Abdullah Hamze,Andre Aumelas, Nga IV, Chung, Peter W. Schiller, Dorothee Berthomieu,Sandor Benyhe, Vincent Lisowski, Jean Martinez, Jean-Francois HernandezPhotolabile Protecting Groups Based on Novel Thiocoumarins andThioquinolones: Synthesis and Photorelease of a Model Amino Acid
Conjugate 8Andrea S.C. Fonseca, M. Sameiro T, Gongalves, Susana P.G. CostaAmino Acid Coupling Reactions in Aqueous Environment Using MicrowaveAssistance Heating 10Athanassios S. Galanis, Fernando AIbericio, Morten GrotliBis-Azobenzene Photoswitchable a-Amino Acids for NanomaterialsApplications 12Alessandro Moretto, Marco Crisma, Paola Fatas, Gema Ballano, Ana I.Jimenez, Carlos Cativiela, Claudio TonioloStabilization of B-Turn Conformation in Melanocortin Like Peptide by ClickSide Chain-to-Side Chain Cyclization 14Chiara Testa, Stefano Carganico, Francesco Nuti, Mario Scrima, AnnaMaria D'ursi, Marvin L. Dirain, Nadeje Lubin Germain, Carrie Haskell-Luevano, Michael Chorev, Paolo Rovero, Anna Maria PapiniImpact of Ionic Liquids on the Conformation of Peptides Studied by HR-MAS NMR Spectroscopy 16Annekathrin Richardt, Carmen Mrestani-Klaus, FrankBordusa
Next Generation Peptide Microarrays 18
F. RalfBischoff, Frank Breitling, Volker Stadler
Imide-Click Ligation and Click-Unclick Peptide-Based Prodrug Strategy 20Reda Mhidia, Nicolas Beziere, Nicole Pommery, AnnickBlanpain, OlegMelnykDesigned Hairpins Modulate the Amyloidogenesis of Alpha Synuclein:Inhibition and Diversion to Non-Amyloid Aggregates 22Niels H. Andersen, Kelly N. L. Muggins, Marco Bisaglio, Liugi BubaccoSelective Targeting of Extracellular Cyclophilins by Novel Cyclosporin ADerivatives
24Miroslav Malesevic, Jan Kiihling, Vikloria Kahlert, Frank Erdmann, Molly A.Balsley, Michael I, Bukrinsky, Stephanie L. Constant, Gunter Fischer
XXV
Design of Peptidyl-Inhibitors for Glutathione Transferase (GST) Useful in
Targeted Cancer Chemotherapy 26
Irine Axarli, Georgia A. Kotzia, Christos Petrou, Paul Cordopatis, Nikolaos
E. Labrou, Yannis D. Clonis
Exploring the HBV Envelope Protein for Liver-Specific Drug Targeting 28
Thomas Miiller, Alexa Schieck, Barbro Beijer, Anja Meier, Uwe Haberkorn,
Stephan Urban, Walter Mier
Biocompatible Triazole Ligations Via 1,3-Dipolar Cycloadditions of Peptidyl
Phosphoranes and Azido Peptides 30
Jorg Rademann, Ahsanullah
Peptide Fragmentomics 32
Alexander A. ZamyatninMolecular Knots As Templates for Protein Engineering: the Story of Lasso
Ducasse, Alain Blond, Jean Peduzzi, Sylvie RebuffatCryptides: Receptors and Signaling Mechanisms for Novel Neutrophil-Activating Peptides Hidden in Mitochondrial Proteins 36
Tert-BuNH2 As An Efficient Reagent for the Deprotection of Fmoc Protected
Amino Acids 50
Armin Arabanian, SaeedBalalaie
Peptide Diketopiperazine Thioester Formation At the Cys-Pro-Cys Position 52
Tom Kawakami, Sakiko Shimizu, Saburo Aimoto
Fmoc Deprotection by Tert-Butylamine in Solution and in the Synthesis of
Cyclic Part of Oxytocin Like Peptides 54
Martin Flegel, Zuzana Flegelovd, Petr Malon, Sixtus Hynie, Vera Klenerovd
xxvi
Radical Scavenging Activity ofHydroxycinnamoylamides of Amino Acids -
Precursors of Biogennic Amines 56Maya G. Chochkova, Hristina G. Nikova, Galya I. Ivanovo, Lyubomir N.
Georgiev, Tsenka S. Milkova
Repetitive Cleavage ofAib-Peptides by Trifiuoroacetic Acid 58Hans Bruckner, Christoph Theis, Thomas Degenkolb, Renate Gessmann,Michael Kokkinidis
Antioxidant Potential of Phenolic Acid Amides ofAromatic Amines 60
Lyubomir N. Georgiev, Iskra Totseva, Katya Seizova.Emma Marinova, MayaG, Chochkova, Tsenka S. Milkova
Solid Phase Synthesis and Characterisation of a Platelet-Derived GrowthFactor Receptor (PDGFR) Specific Affibody Molecule 62Bard Indrevoll, Roger Bjerke, Dimitrios Mantzilas, ErlendHvattum, Astri
RogstadRacemization of Amino Acids on Heating with Sugars Or
(Hydroxyalkyl)Aldehydes Or -Ketones 64
Hans Briickner
Nicotianamine and Thermonicotianamine: Supported Synthesis and Chelation
Ability 66
Manuel Larrouy, Jean Martinez, Florine Cavelier
Tert-Butylation of Hydroxy 1 Group Using MTBE 68
Sorour Ramezanpour, Saeed Balalaie
Synthesis of New Polymer Matrices Including Amino Acids 70Dantcho L. Danalev, Jean-Marie Ringeard, Stephane Serfaty, Jean-Yves Le
Huerou, Emmanuel Caplain, Lyubov K. Yotova, Pascal Griesmar
Convenient Synthesis ofTfm-Dipeptides from Unprotected Enantiopure Alfa-Tfm-Proline and Alfa-Tfm-Alanine 72
Gregory Chaume, Nathalie Lensen, Caroline Caupene, Thierry BrigandConcise Access to (S)- and (R)-Alfa-Tfm Serine and Alfa-Tfm Aspartic Acidfrom Chiral Trifluoromethyloxazolidines (Fox) 74
WitoldA. Neugebauer, Anna Kwiatkowska, Xue Wen Yuan, Robert DaySolid-Phase Synthesis C-Terminus Chloromethyl Ketone Peptides 80
Witold A. Neugebauer, Nabil G. Seidah, Delia Susan-Resiga, Xue Wen Yuan,Robert DayPhoto-Uncaging of Neurotransmitter Amino Acids from Fluorescent 5,6-Benzocoumarinyl Precursors 82
Maria Jose G. Fernandes, M. Sameiro T. Gonqalves, SusanaP.G. Costa
What Could Be the Role ofQuinacrine in Creutzfeldt-Jakob Disease
Treatment? 84
Zbigniew Zawada, Jaroslav Sebestik, Martin Safaflk, Anna Krejcifikova,Anna Bfezinovd, Jan Hlavdcek, Ivan Stibor, Karel Holada, Petr Bour
xxvii
Synthetic Antifreeze Glycopeptide Analogs 86
Lilly Nagel
Peptide Based Artificial Receptors for Carbohydrate Recognition 88
Predrag Cudic, Andreja Jakas, Nina Bionda, Mare Cudic
Synthesis of Glycopeptides Potential Inhibitors ofHuman Rhinovirus 3c
Prorease 90
Dantcho L. Danalev, Nadege Lubin-Germain, Jacques Uziel, Jacques AugeStereoselective Synthesis of Tetrahydro-B-Carbolines Via Pictet-SpenglerReaction 92
Saeed Balalaie, Vahid Dianati
Synthesis of Aza-B3-Homoserine, Incorporation of This New Aza-B3-Amino
Acid into 26rfa(20-26) and Microwave-Assisted Deprotection of Its Side
Chain 94
Olivier Tasseau, Patrick Bauchat, Cindy Neveu, Benjamin Lefranc, Jerome
Leprince, Michele Baudy-Floc 7?
Dimerization ofthe Immunosuppressory Decapeptide Ubiquitin Fragment 96
Marzena Cydzik, Monika Biernat, Alicja Kluczyk, Piotr Stefanowicz,Remigiusz Bqchor, Michal Zimecki, Zbigniew SzewczukThe Application ofthe New Tin(IV) Chloride Deprotection for the
Luis S. Monteiro, Joanna Kolomanska, Ana C. Suarez
The Total Regioselective Control of Tartaric Acid 130Jan Spengler, Ana I. Femdndez-Llamazares, Javier Ruiz-Rodriguez, Klaus
Burger, Fernando Albericio
DTT Reacts with TFA to Form a Novel Bicyclic Dithioorthoester 132Jan Pawlas, Stefan Hansen, Anne H. Sorensen, Gannar Staerkaer, Anette
Moller, Neil Thompson, Thomas Pagano, Fangming Kong, Steve Koza, MarkPozzo, Jari Finneman, Patricia DroegeSolid Phase Synthesis of Structurally Diverse 1,2,5-Benzothizadiazepin-4-on-1,1-Dioxides'
'
134
Karel-Simon Slock, Jurgen Caroen, Johan Van Der EyckenEvaluation of Packing Materials Used for Preparative HPLC Purification of
Solid-Phase Synthesis of the Lipopeptide Myr-Hbvpres/2-78, a Hepatitis BVirus Entry Inhibitor 172
Alexa Schieck, Thomas Midler, Uwe Haberkorn, Stephan Urban, Walter Mier
xxx
Automated Microwave-Assisted Peptide Synthesis with a Novel Robotic
Synthesizer: Synthesis of Difficult Sequences 173
Soren L. Pedersen, Amit Mehrotra, KnudJ. Jensen
The Oxime-Based Family of Coupling Reagents 176
Ramon Subiros-Funosas, Ayman El-Faham, Fernando Albericio
Engineering of Amyloid-B-Binding Affibody Molecules for ImprovedChemical Synthesis and Higher Binding Affinity 178
Joel Lindgren, Lars Abrahmsen, Sebastian Warml&nder, Amelie Eriksson
Karlstrom
Chemical Synthesis of Fluorescent-Labeled Affibody Molecules for Use in
Cancer Diagnostics 180
Anna Perols, Amelie Eriksson Karlstrdm
Oxyfold : A New Solid Supported Reagent for the Simple and Effective
Formation ofDisulfide Bond in Peptides 182
Luisa Ronga, P. Verdie, M. Cristau, M. Amblard, S. Cantel, C. Enjalbal, K.
Puget, G. Subra, Jean Martinez
An Efficient MW-Assisted Synthesis of Dicarba-Analogues 184
G. Cane, A. Di Cianni, M. Litmini, Anna Maria Papini, Mauro Ginanneschi
Microwave-Assisted Solid Phase Synthesis of [Asn641(Glc)]FAN(635-655):A New Case Study for Optimisation of Glycopeptide Synthesis 186Fabio Rizzolo, Francesco Nuti, Shashank Pandey, Mario Chelli, Paolo
Rovero, Anna Maria PapiniConventional and Microwave-Assisted SPPS Approach: A ComparativeStudy ofPthrp(l-34)NH2 Synthesis 188
Fabio Rizzolo, Chiara Testa, Michael Chorev, Mario Chelli, Paolo Rovero,Anna Maria PapiniMicrowave-Assisted Total Synthesis ofMacrocvclic Cystine Knot
Miniproteins 190
S. Park, S. Gunasekera, T. Aboye Teshome, UlfGoransson
Racemization in Automated Solid Phase Synthesis 192
KrzysztofDarlak, Miroslawa Darlak, Thomas E. HopkinsOctapeptide Ligands with Affinity for Recombinant Erythropoietin Derivedfrom the Screening of Combinatorial Libraries 194Maria C. Martinez-Ceron, Mariela M. Marani, Marta Tattles, Marina
Etcheverrigaray, Fernando Albericio, Osvaldo Cascone, Silvia A. CamperiPost-Synthesis Modification ofP-lodo-Phenylalanine-Containing Peptides on
Solid-Phase Via the Palladium-Catalyzed Sonogashira Reaction 196
Ngoc-Duc Doan, David Chatenet, Alain Fournier
Specific Substrates and Inhibitors of Human Furin 198
Adam Lesner, Magdalena Wysocka, Anna Lqgowska, KrzysztofRolkaNovel Peptide Conjugates: Heterocyclic Modifications of the
Immunomodulatory Ubiquitin Fragment 200
Alicja Kluczyk, Malgorzata Ratajska, Anna Staszev/ska, Marek Cebrat, Hubert
Bartosz-Bechowski, Piotr Stefanowicz, Michal Zimecki, Zbigniew SzewczukThe Characterization of Staphopains Enzyme Family from StaphylococcusAureus Using Combinatorial Chemistry Methods 202
Adam Lesner, Magdalena Wysocka, Marcelina Jams, Anna Lqgowska, KatarzynaGuzow, Grzegorz Dubin, Benedytkt Wladyka, Wieslaw Wiczk, Krzysztof'Rolka
xxxi
Convergent Syntheses ofHuprpl06-126 (Difficult Sequence) Using Native
Chemical Ligation and Desulfurization/ Deselenization 203
Jaroslav Sebestik, Martin SafaHk, Zbigniew Zawada, Jan Hlavdcek
Functionalized PNA Backbone Building Blocks Eligible for Diels Alder
Click Chemistry in Molecular Imaging 206
Rildiger Pipkorn, M. Wiefiler, Waldemar Waldeck, Mario Koch, Klaus Braun
Fmoc Solid Phase Synthesis ofPeptide Thioesters for Native Chemical
Ligations Employing a Tert-Butyl Thiol Linker 208
RichardRaz, Jorg Rademann
Assembly and Stimulatory Activity of Backbone to Side Chain Cyclic
Octapeptide-Ligands for the N-Terminal SH2-Domain ofthe Protein-
Tyrosine-Phosphatase SHP-1 210
MohammadS. Zoda, Martin Zacharias, Franziska Mussbach, Buerk
Schaefer, Siegmund Reissmann
Synthesis of Neuropeptide Y Analogues As PET Imaging Agents 212
Simon J. Mountford, Lei Zhang, Herbert Herzog, Bim Graham, Philip E.
Crystal Structure of L68V Mutant ofHuman Cystatin C, An AmyloidogenicProtein 282
Marta Orlikowska, Elzbieta Jankowska, Dominika Borek, ZbyszekOtwinowski, Aneta SzymanskaMutants of An Amyloidogenic Human Cystatin C in Pressure-Induced
Denaturation Studies Using Hydrogen Exchange Mass Spectrometry 284
Elzbieta Jankowska, Marta Orlikowska, Marta Sosnowska, Aneta
Szymanska, Piotr Stefanowicz, Karolina Kowalewska, Zbigniew Szewczuk
Characteristics of a Human Cystatin C - Antibody Complex 286
Anna Sladewska, Aneta Szymanska, Aleksandra Kolodziejczyk, Anders
Grubb, Paulina CzaplewskaCharacterization of Human Cystatin C - Serum Amyloid A Complex 288
Marta Spodzieja, Aneta Szymanska, Anna Sladewska, Piotr Stefanowicz,Zbigniew Szewczuk, Zbigniew Grzonka, Claudia Cozma, Michael Przybylski,
Aleksandra Kolodziejczyk, Paulina CzaplewskaRecognition ofCytoskeletal Proteins Monoclonal Iggs by CSF114(Glc), the
Synthetic Probe of Multiple Sclerosis 290
ShashankPandey, Duccio Lambardi, Feliciana Real-Fernandez, Maria
Claudia Alcaro, Elisa Peroni, M. Chelli, A. M. Papini, F. Lolli, Paolo Rovero
xxxiv
Role of Triple Hyp-Pro Substitution on Conformation and Bioactivity ofIntegramide A 292Marta De Zotti, Wim De Borggraeve, Bernard Kaptein, Quirinus B.
Broxterman, Sheo B. Singh, Peter J, Felock, Daria J. Hazuda, Fernando
Formaggio, Claudia Toniolo
Angiotensin 1 Converting (ACE) Inhibitor)' Peptides - A Bioinformatic-Assisted Idea of Research 294
Anna Iwaniak
A Method for Screening Peptides Bound to EGFR by Using MultipleFluorescent Amino Acids As Fluorescent Tags 296
Improving Peptide Therapeutics for HIV and Other Viral Diseases 298Antonello Pessi, Matteo Porotto, Christine Yokoyama, Laura M. Palermo,Aparna Talekar, Ilaria Devito, Barry Rockx, Heinz Feldmann, Riccardo
Cortese, Anne Moscona
De Novo Designed Cyclic Decapeptides with Anticancer Activity 300Lidia Feliu, Gloria Oliveras, Anna D. Cirac, Cristina Roses,Ramon Colomer, EduardBardajl, Marta Planus, Teresa PuigSynthesis of Tacrine Analogues Comprising Peptide Moiety 302
Dantcho L. Danalev, Lyubomir T. Vezenkov, Nikola}' Vassilev
Inhibition of Amyloid Formation in Model Peptides 304
Enrico Brandenburg, Hans V. Berlepsch, Beate Koksch
Synthesis and in Vitro Characterization of New, Potent and Selective
Oxytocin Receptor Agonists 306
Kazimierz Wisniewski, Robert Galyean, Claudia D. Schteingart, Hiroe
Tariga, Glenn Croston, Sudarkodi Alagarsamy, Pierre J.-M. RiviereAmidine Neighbouring-Group Effect on the Stability of B9870, a HighlyPotent Anti-Cancer Bradykinin B1/B2 Antagonist Peptide Dimer 308
Lajos Gera, Richard Duke, Daniel C. Chan, Paul A. Bann, Robert S. Hodges,John M. Stewart, James BlodgettSynthesis and Biological Evaluation of Cytotoxic Peptide ConjugatesContaining 5-Fluorouracil 310
Sergey V. Burov, Tatyana V. Yablokova, Maria V. Leko, Anton Yu. Alenko,Marina Yu. Dorosh
Immunopepdb a Novel Immunomodulatory Peptides Database 312Osmar N. Silva, William F. Porto, Diego G. Gomes, Simoni S. Dias, OctavioL. Franco
Delta-Sleep Inducing Peptide (DSIP) and Its Analogues: Studies on Their
Therapeutic Potency 314/. /. Mikhaleva, J, A. Prudchenko, E. S. Efremov, L. V. Onoprienko, L. D,
Chikin, R. I. Yakubovskaya, E. P. Nemtsova, O. A. Bezborodova
Mechanism in Inhibition of Histone Deacetylase by Cyclic Tetrapeptides withVarious Functional Groups 350Md. Shahidid Islam, Md. Nurul Islam, Nsiama Tienabe, Naoto Oishi, TamakiKato, Norikazu Nishino, Akihiro Ito, Minoru Yoshida
Anti-Plasmodium Effects ofAngiotensin II Analogues 352
VaniX. Oliveira, Mayra Chamlian, Ceres Maciel, MargarethL. Capurro,Antonio Miranda
Targeted Platinum Peptide Complexes Holding Diamino and DicarboxylicCoordination Modes 354
Agnieszka M. Glowinska, Anna Lesniak, Marzena Lazarczyk, Ewa Matyja,Andrzej W. Lipkowski, Aleksandra Misicka
Preclinical Pharmacokinetics ofMyrcludex B, a Novel Entry Inhibitor for theTreatment of HBV Infections 356
Alexa Schieck, Anja Meier, Thomas Midler, Uwe Haberkorn, Walter Mier
Chemical Modification ofNatural Immunomodulators Tuftsin and MuramylDipeptide Significantly Influence Their Biological Activity 358Anna Wardowska, Kiystyna Dzierzbicka, Malgorzata Rogalska, PiotrTrzonkowski
Synthesis and Antimicrobial Evaluation of Temporin L AnaloguesContaining D-Amino Acids 360
Alfonso Carotenuto, Maria Luisa Mangoni, Ludovica Marcellini Hercolani
Gaddi, Maria Rosaria Saviello, Salvatore Di Maro, Pietro Campiglia, IsabelMonterrey-Gomez, Luigia Auriemma, Ettore Novellino, Paolo Grieco
Conjugates of Tuftsin and Muramyl Dipeptide As Stimulators of Monocyte-Derived Dendritic Cells 362Anna Wardowska, Krystyna Dzierzbicka, Agnieszka Menderska, Piotr
Trzonkowski
Synthesis of Peptide Analogs of the A2 Subunit (Sequence 558-565) ofthe
Factor Fviiia of Blood Coagulation 364
Charts Anastasopoulos, Yiannis Sarigiannis, George StavropoulosPeptides Versus Nonpeptides As Therapeutics: An Exciting Challenge for
Big Pharma 366
Maurice Manning, Stoytcho Stoev, KrzysztofBankowskiFluctuations and the Rate-Limiting Step of Peptide-Induced Membrane
Leakage 368
C. Mazzuca, B. Orioni, M. Coletta, F. Formaggio, C. Toniolo, G. Maulucci,M. De Spirito, B. Pispisa, M. Venanzi, L. Stella
Effect of Helix Kink on the Activity and Selectivity of An Antimicrobial
Peptide'
370Sara Bobone, Gianfranco Bocchinfuso, Antonio Palleschi, Jin Y. Kim,Yoonkyung Park, Kyung-Soo Hahm, Lorenzo Stella
Membrane Insertion of Para-Cyanophenylalanine Labeled Alamethicin
Analogues. Correlation of Fluorescence and Infrared Absorption Data 372
S. Bobone, M. De Zotti, A. Bortolotti, G. Ballano, F. Formaggio, C. Toniolo, L. Stella
Cell-Penetrating Peptides As Adenovirus Vector Carrier 374
K. Kawasaki, S. Kida, Y. Eto, Y. Yoshioka, S. Nakagawa, K. Hojo, M. Maeda
Jelleine-I Analogues with Improved Antibacterial Activity 376
Revealing the Lytic Mechanism ofthe Antimicrobial Peptide Gomesin by OpticalMicroscopy ofGiant UnilamellarVesicles and Isothermal Titration Calorimetry 400
TatianaM. Domingues, Joachim Seelig, KarinA. Riske, Antonio Miranda
Study ofa New Maurocalcine CPP Analogue Devoid ofPharmacological Activity 402
Cathy Poillot, Michel De Waard
Comparison ofthe Mechanism of Action of Antimicrobial Peptides on Giant
Unilamellar Vesicles Via Optical Microscopy 404
MartaN.C. Martins, TatianaM. Domingues, KarinA. Riske, A. Miranda
xxxviii
Lasiocepsin: Novel Antimicrobial Peptide from the Venom of Eusocial Bee
Lasioglossum Laticeps 406Lenka Monincovd, Jirina Slaninova, Vladimir Fucik, Oldfich Hovorka,Zdenek Voburka, Lucie Bedndrovd, Petr Malon, Vaclav CefovskySelective Membrane Interactions ofNucleolar-Targeting Peptides 408Margarida Rodrigues, Gandhi Radis-Baptista, Beatriz G. De La Torre,Miguel Castanho, David Andreu, Nuno C. SantosInteractions of Cell-Penetrating Peptides in the Model of Giant PlasmaMembrane Vesicles 410
Pille Saalik, Aira Niinep, Mats Hansen, Ulo Langel, Margus PoogaAntimicrobial Oligopeptides and Rapid Alkalinization Factors in Chilean
Grape 412
Alexander A. Zamyatnin, OlgaL. Voronina
Glycine and Histidine-Rich Antifungal Peptides: on the Way to the Mode ofAction of Shepherin I 414Cesar Remuzgo, Thiago R. S. Lopes, Thais S. Oewel, GldnciaM. Machado-Santelli, Sirlei Daffre, M. Teresa Machini Miranda
Targeting the Nuclear Pore Complex with Proteomimetic Cell PenetratingPeptides 416
Sarah Jones, John Howl
Antimicrobial Protein Analyzer (AMPA): A Computational Tool to ScreenAntimicrobial Domains in Proteins and Peptides 418
Marc Torrent, DavidAndreu
Analogs of Contulakin-G, An Analgetically Active Glycopeptide from Conus
Geographus 420
Samson Afewerki, Ola Blixt, Henrik Clausen, Thomas NorbergActive Peptidomimetic Insect Kinin Analogs with Type VI Turn Motif 4-
Aminopyroglutamate Lack Native Peptide Bonds 422KrzysztofJ. Kaczmarek, Geoffrey M. Coast, Janusz Zabrocki, Ronald J.
Nachman
Synthesis and Bioactivity Studies on the C-Terminally ExpressedHeptapeptide Orthologues of Various Proenkephalin A Sequences 424
Fruzsina Babos, Engin Bojnik, Sandor Benyhe, Anna MagyarSubstitution ofVarious P-N-Alkylcarboxamidophenylalanine Analogues for
Tyrl in T1PP Opioid Peptides."
426
Irena Berezowska, Carole Lemieux, Nga N. Chung, Peter W. Schiller
NMR Studies of Vasopressin Analogues Modified with Indoline-2-
Carboxylic Acid in Position 2 in Dodecylphosphocholine Micelle 428
Emilia Lubecka, Emilia Sikorska, Anna Kwiatkowska, Jerzy Ciarkowski
Synthesis of New Lgnrh-III Analogues and Studies on Prostate Cancer Cell
Proliferation 430
Paul Cordopatis, Eleni V. Pappa, Aikaterini A. Zompra, Zinovia Spyranti, Zoi
Diamantopoulou, Fotini N. Lamari, Panagiotis Katsoris, Georgios A.
SpyrouliasNew Analogues of Arginine Vasopressin and Its Selected Agonists ModifiedAt Position 2 with (S)-2-(l-Adamantyl)Glycine 432BernardLammek, Anna Kwiatkowska, Dariusz Sobolewski, Lenka
Borovickovd, Jirina Slaninova, Adam Prahl
xxxix
Interaction of Curcumin with A-Synuclein and Its Relationship to Curcumin's
Ability to Inhibit Fibril Deposit 434
Anna Marchiani, Stefano Mammi, Isabella Tessari, Luigi Bubacco, Sandra
Monti, Francesco Manoli, Paolo Ruzza
Synthesis, Antiproliferative Activity on Prostate Cancer Cells, Enzymatic
Stability and Conformational Studies of New Gnrh Analogues 436
FotiniN. Lamari, Eleni V. Pappa, Zinovia Spyranti, Aikaterini A. Zompra,Zoi Diamantopoulou, Panagiotis Katsoris, George Liapakis, Ceorgios A.
Spyroulias, Paul CordopatisAnalogues of Neurohypophyseal Hormones, Oxytocin and Arginine
Vasopressin, Conformationally Restricted and Acylated in the N-Terminal
Part ofthe Molecule 438
Dariusz Sobolewski, Anna Kwiatkowska, Lenka Borovickovd, Jifina
Slaninovd, Adam Prahl
Side-Chain to Side-Chain Cyclization ofOpioid Peptides Enhances
Proteolytic Stability of Their Exocyclic Peptide Bonds 440
Marek Cebrat, Piotr Stefanowicz, Alicja Kluczyk, Zbigniew Szev/czuk,Katarzyna Filip, Malgorzata Ciszewska, Janlzdebski
George K. Daletos, Margarita Lamprou, Panagiotis Zoumpoulakis, Maria
Zervou, Nikos L. Assimomytis, Athina Geronikaki, Evangelia Papadimitriou,Vassiliki Magafa, Paul CordopatisSynthesis and Biological Evaluation ofNew Linear and Cyclic Analogues of
Neurotensin 446
R. Exarchakou, V. Magafa, E. Manessi-Zoupa, N. L. Assimomytis, M.
Georgiadou, M. Venihaki, G. Varvonnis, G. Liapakis, P. CordopatisInfluence ofNon Natural Amino Acids At Position 3 of [Mpal, D-Tyr(Et)2]Or [Mpal, D-1-Nal2] Oxytocin on Their Pharmacological Properties 448
Vassiliki Magafa, N. L. Assimomytis, George Pairas, Revekka Exarchakou,George K, Daletos, Lenka Borovickovd, Jifina Slaninovd, Paid CordopatisConformational Behaviour of Vasopressin-Like Peptides in the Membrane-
Mimetic Environment 450
Emilia Sikorska, Anna Kwiatkowska
Ml 154 - A Novel Galanin Ligand to Delineate the Galaninergic System 452
Johan Runesson, Indrek Saar, Rannar Sillard, Ulo LangelDesign, Synthesis and Biological Evaluation ofNovel Endomorphins with
Multiple Structural Modifications 454
Geza Toth, Jayapal Reddy Mallareddy, A. Borics, K. E. Kdver, A. Keresztes
A Neuropeptidomics Study ofthe Bovine Hypothalamus Reveals Novel
Endogenous Peptides and Processing Pathways 456
Michelle L. Colgrave, LiXi, SigridLehnert, Traute Flatscher-Bader, Henrik
Wadensten, Anna Nilsson, Per E, Andren, Gene WijffelsSynthesis, Conformational Analysis, and Biological Activity of [Aza-3-Indoylgly4] GHRP-6 as an Aza-Tryptophan Analog of Growth Hormone
Releasing Peptide-6 458
C. Proulx, DavidSabatino, Petra Pohankova, Huy Ong, William D. Lube11
xl
N-Linked Homodimers of the Kinin Bl Receptor Antagonist R-715 460WitoldA. Neugebauer, Martin Savard, Klaus Klarskov, Fernand GobeilIdentification of a New Citrullinated Epitope on Filaggrin for the EarlyDiagnosis of Rheumatoid Arthritis 462Fruzsina Babos, Eszter Szarka, Adam Bartos, Gydrgy Nagy, GabriellaSdnnay, Anna Magyar, Ferenc Hudecz
4-Methylpseudoproline Analogues of Cyclolinopeptide A: Synthesis,Conformation and Biology 464
J. Katarzynska, S, Jankowski, K. Hubert, Michal Zimecki, Jamisz ZabrockiDesign, Synthesis and Stability Studies of Potent Inhibitors ofPro-ProteinConvertases (Pes) 466A. Kwiatkowska, N. Chevalier, R. Desjardins, F, Couture, F. D 'anjou, S.Routhier, C. Levesque, Y. Dory, W. A. Neugebauer, R. DayA New Class ofSomatostatin Analogues with Antiproliferative Activity inHuman Cancer Cells 468Yuko Tsuda, Anna Miyazaki, Emiko Okuno, Isoko Kuriyama, YoshiyukiMizushina, Hiromi Yoshida
Analogues of Trypsin Inhibitor SFTI-1 Modified in Absolutely Conserved PI'Position by Synthetic Or Non-Proteinogenic Amino Acids 469Rafal Lukajtis, Anna Lqgowska, Dawid Debowski, Magdalena Wysocka,Adam Lesner, KrzysztofRolkathe Influence of Disulfide Bridge of Trypsin Inhibitor SFTI-1 for Enzyme -
Inhibitor Interaction 472Anna Lggowska, DaM>id Debowski, Magdalena Wysocka, Adam Lesner,KrzysztofRolkaB-Cell Epitope Mapping of Immunodominant Proteins in PemphigusVulgaris: Prediction, Synthesis, and Immunoserological Evaluation 474Hajnalka Szabados, Szilvia Bosze, Antal Blazsek, Pdlma Sillo, SaroltaKdrpdti, Ferenc Hudecz, Ratalin UrayT-Cell Epitopes in Autoimmune Bullous Skin Disorders 476Katalin Uray, Mdrta Marschalko, Hajnalka Szabados, Antal Blazsek, FerencHudecz, Sarolta Kdrpdti, Szilvia Bosze
The Transcriptional Activator Phob; Chemical Synthesis of Epitopes andFunctional Studies
478Markus Ritzefeld, Katrin Wollschldger, Andre Komig, Michael Birlo, RobertRos, Dario Anselmetti, Norbert Sewald
Assay of Histone Methyltransferases Using Ac-Peptidyl-MCA As Substrates 480Norikazu Nishino, Tienabe K, Nsiama, Hongfang Chi, Yasushi Takemoto,Akihiro /to, Minoru Yoshida
Molecular Modeling, Design and Structural Studies of a New Class of PeptideInhibitors of Bacterial Topoisomerases 482Luiz Carlos B. Barbosa, S. S. Garrido, D. B, Delfino, A. Garcia, R. MarchettoStructural Aspects and Biological Evaluation ofNew Mannose Derived
Phakellistatins: Are They True Active Natural Products? 490
Marta Pelay-Gimeno, Judlt Tidla-Puche, Andres M. Francesch, Carmen
Cuevas, Fernando Albericio
Celiac Disease: Synthesis of Overlapping Linear Peptide Epitopes of Ttg[Aa(l-230)] 492
Margherita Di Pisa, Giuseppina Sabatino, Mario Chelli, Paolo Rovero,Claudia Tiberti, Anna Maria PapiniCeliac Disease: Characterization ofAmino Acids and Short Peptides FingerPrint for a Fast I.V.D. 494
Margherita Di Pisa, Giuseppina Sabatino, Mario Chelli, Paolo Rovero,Claudio Tiberti, Anna Maria Papini
Search for Inhibitors Or Activators ofHuman Proteasome 496
R. Rostankowski, Elzbieta Jankowska, M. Gaczynska, P.A. Osmulski, S,
Madabhushi, Franciszek KasprzykowskiCharacterisation of the Minimal Epitope Detecting Autoantibodies in
Multiple Sclerosis by Surface Plasmon Resonance 498
Feliciana Real-Fernandez, Irene Passalacqua, Elisa Peroni, Francesco Lolli,Paolo Rovero, Anna Maria PapiniAntigenic Probes for Autoantibody Detection in Multiple Sclerosis: SyntheticPeptides Versus Recombinant Proteins 500Francesco Gori, Barbara Mulinacci, Lara Massai, Francesco Lolli, Anna
Maria Papini, Paolo Rovero
The Metabolisation of Different lodinated Peptide Species 502
Bart De Spiegeleer, Sylvia Van Dorpe, EwaldPauwels
Rational Design and Optimization ofthe Newly Designed GlycopeptideSequence to Develop the Diagnostic/Prognostic Assay for Multiple Sclerosis 504
Shashank Pandey, Elisa Peroni, Paolo Rovero, Francesco Lolli, Anna Maria
PapiniStructure-Function Relationships of a Hexapeptide Fragment ofthe
Carcinoembryonic Antigen 506
Sdndor Lovas, Nicholas Y. Palermo, Peter Thomas, Richard F. MurphyTying Up Loose Ends: Beta Capping Units As Non-Covalent Staples for
Loops and As Dynamics Probes 508
Brandon L. Kier, Irene Shu, Jackson Kellock, Niels H. Andersen
Two Short Peptides That Arise in Inflammation Demonstrated StrongNeuroprotective Effects in Vitro 510
Vsevolod G. Pinelis, Tatyana N. Storozhevykh, Kristina V. Glebova, TatyanaN. Danyukova, Yana E. Senilova, Stanislav I. Schramm, N. F. MyasoedovNeuroprotective Effect of Short Collagen-Related Peptides and Their Abilityto Interact with ACE Reveal Structure-Activity Similarity 512Stanislav I. Schramm, Tatyana N. Danyukova, Kristina V. Glebova, Igor Yu.
Nagayev, Ludmila A. Andreeva, Nikolay F. MyasoedovDesign and Synthesis of Guanidinium-Rich Molecular Transporters for DrugDeliver}' 514
Tatyana A. Dzimbova, Kaloyan Georgiev, Tamaral. Pajpanova
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Synthesis and Biological Evaluation of Daunorubicin-Gnrh-III Prodrug 516
Rdzsa Hegediis, Erika Orban, lldiko Szabo, Marilena Mama, Gdbor MezoThe [Tc(N)PNP] Metal Fragment Labeled Peptide for MCI ReceptorsImaging: Preliminary Studies 518Barbara Biondi, Cristina Bolzati, Davide Carta, Nicola Salvarese, FiorenzoRefosco, Andrea Calderan, Paolo Ruzza
Kinetic Studies on Cellular Uptake of Polyarginine Peptide Using FRET 520Akihiro Ambo, Yasuyuki Suzuki, Motoko Minamizawa, Yusuke Sasaki
Synthesis and in Vitro Antitumor Activity of New Daunomycin ContainingGnrh-11 Derivatives
Anthracycline-Gonadotropin Releasing Hormone-III Bioconjugates:Synthesis, Antitumor Activity and in Vitro Drug Release 524Gdbor Mezo, Ulrike Lenrs, Pascal Schlage, Erika Orbdn, lldiko Szabo,Szilvia Bosze, Marilena Manea
Design and Synthesis of Polyfunctional Spacers Based on BiodegradablePeptides 526LyubovA. Yarinich, Lyudmila S. Koroleva, Tatyana S. Godovikova, VladimirN, Silnikov
Amino Acids Esters ofAcyclovir-Synthesis and Antiviral Activity 528Ivanka G. Stankova, Stoyan Shishkov, Kalina Koslova, Daniel Todorov,Luchia Mukova, Angel Galabov
Homobivalent a-MSH Derivatives for Melanoma Imaging: 99mtc(CO)3-Labeling and Biological Evaluation 530M. Morals, P. D. Raposinho, M. C. Oliveira, JoaoD.G. Correia, I. SantosDevelopment of Drug Delivery Systems for Targeted Cancer ChemotherapyBased on Gnrh Antagonist and Agonist Peptides 532Bence Kapuvdri, Borbdla Vincze, Marilena Manea, Miguel Tejeda, AkosSchulcz, JozsefTovdri, Dezso Gadl, Erika Orbdn, lldiko Szabo, Gdbor Mezo
Frederic Zoller, Christain Hauer, A. Markert, Uwe Haberkorn, Walter Mier
Synthesis and Characterization ofNovel Dipeptide Ester ofAcyclovir 536
Ivanka G. Stankova, Ivanka B. Stoineva, Michaela SchmidtkeNew Socsl-Kir Mimetic Peptides Through the Screening of Focused
Si mplified Combinatorial Libraries 538
Daniela Marasco, Nunzianna Doti, Pasqualina L. Scognamiglio, StefaniaMadonna, Menotti Ruvo, Carlo Redone, Cristina Albanesi
Utilization of Enzymes from the Red King Crab Hepatopancreas forObtainment ofCow Milk Protein Hydrolyzate 540
V.A. Mukhin, Yu. E. Trukhacheva, V. Yu. Novikov
Isovaline Containing Peptides: Configurational Assignment Using 2d-Nmr
Spectroscopy 542Marta De Zotti, Elisabetta Schievano, Stefano Mammi, Bernard Kaptein,Quirinus B. Broxterman, Sheo B. Singh, Hans Briickner, Claudio TonioloCyclic PDZ-Binding Peptides As Neuroprotective Agents AgainstExcitotoxic Brain Damage 544
Brian MAusten, Kate Duberley, Paul Turner, Ruth Empson
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Cellular Expression of the Human Angiotensin II Type 1 Receptor Containingthe Non-Canonical Photolabelling Amino Acid Bpa 546
Jason Arsenault, Julie Lehoux, Brian J. Holleran, Marilou Lefrangois,Gaetan Guillemette, Richard Leduc, Emanuel Escher
The Synthesis of Some Peptides Intended to Be Inhibitors of the RNA-
Polymerase of Influenza A Virus. 548
Oleg V. Matusevich, OlegI. Kiselev
The Adjuvant Activity of Glucosaminyl Muramyl Dipeptide (GMDP) Is
Linked to the Beta-Anomer Configuration and N-Acetylglucosamine(Glcnac) Uptake System. 550
Elena A. Meshcheryakova, Elena P. Dobrashkina, Tatyana M. Andronova,
Vadim T. Ivanov
Peptide Inhibitors of the Intrinsic Pathway of Apoptosis Targeting CARD-CARD Interactions 552
Yadira Palacios-Rodrigiiez, Guillermo Garcia-Lainez, Mar Orzdez, EnriquePerez-PaydSecondary Structure Modifications of Serine Protease Inhibitor Upain-1 to
Improve Binding Affinity 554
Renee Roodbeen, Peter A. Andreasen, Knud J. Jensen
Structural and Biophysical Studies of Ribose-5-Phosphate Isomerase A from
Francisella Tularensis 556
R, Rostankowski, Marta Orlikowska, Dominika Borek, C. Brautigam, T.
Scheuermann, Zbyszek Otwinowski
Simplified T-Defensins: Search for New Antivirals 558
Piotr Ruchala, Sylvia Cho, Amy L. Cole, Chun-Ling Jung, Hai T. Luong, EwaD. Micewicz, Alan J. Waring, Alexander M. Cole, Betsy C. Herold, Robert I.
Lehrer
Venomics: Targeted Drug Discovery and Lead Optimisation Using Animal
Venoms 560
Reto Stdcklin, Estelle Bianchi, Daniel Biass, Cecile Cros, Dominique Koua,Frederic Ferret, Aude Violette, Philippe Favreau
Application of Conjugated Glutamic Acid Peptide (GAP) to a Novel 4-
Anilinoquinoline EGFR Inhibitor for Tumor-Targeted Imaging 562
Hamada, Yuuki Takada, Hisashi Endo, Ukihide Tateishi, Takashi Oka,Kazuhiro Ogata, David J. Yang, Tomio lnoue
Quantifying Molecular Partition of Charged Molecules by Zeta-Potential
Measurements 564Joao Miguel Freire, Marco M. Domingues, Joana Matos, Manuel N. Melo,
Ana Salome Veiga, Nuno C. Santos, Miguel Castanho
Ccdb Toxin Peptides Derivatives and Its Interactions with an Analogue of
Bacterial Ccda Antitoxin 566
Saulo S. Garrido, CamilaAp. Cotrim, DaviB. Delfino, Anderson Garcia,Luiz Carlos B. Barbosa, Reinaldo Marchetto
A Regulator}' Role for the Muramyl Peptide (GMDP) in a Murine Model of
Allergic Asthma 568
Svetlana V. Guryanova, M. A. Shevchenko, I. G. Kozlov, T. M. Andronova
Molecular Dynamics ofAmylin Amyloid Single and Multiple Beta Sheets 570
D, Lapidus, Salvador Ventura, Cezary Czaplewski, Adam Liwo, Inta Liepina
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Molecular Modeling of Single and Multiple Beta-Sheets of Amyloid BetaProtein 25 - 35
572Vita Duka, Isabella Bestel, Cezary Czaplewski, Adam Liwo, Inta LiepinaNew Hybrid and Mutant PIA and Mil Toxins with Greater Affinty andSelectivity for the A6* Subtype 574R Longhi, L. Pucci, L. Rizzi, G. Grazioso, C. Dallanoce, F. Clementi, C. GottiMolecular Modeling of Novel Gnrh Analogues Using NMR Spectroscopyand Relation with Their Anti-Cancer Activities 576F. Tahoori, M. Erfani Moghaddam, Armin Arabanian, Saeed BalalaieSynthesis ofNovel Peptides Containing Unusual G-Amino Acids andInvestigation of Their Nanostructures 57 8B. Talaei, Armin Arabanian, Saeed Balalaie
Structural Control of Diastereomeric Leu-Leu-Aib-Leu-Leu-Aib Sequences 580
Y. Demizu, M. Doi, Y. Sato, M. Tanaka, H. Okuda, M. Kurihara
Optical Spectroscopy and Conformational Analysis of Peptide Aggregates,the Role of Aromatic Interactions and Conformational Flexibility 582M. Caruso, E. Placidi, E. Gatto, L. Stella, A. Palleschi, G. Bocchinfuso, F.
Formaggio, C. Toniolo, M. Venanzi
Mapping Charge Derealization in a Peptide Chain Triggered by Oxidationof a Terminal Ferrocene Moiety 584V. Marcuzzo, A. Donoli, R. Cardena, A. Moretto, C. Toniolo, S. Santi
Paterno-Yang Photocyclization Reaction in Bpa/Met 3-10-Helical Peptides:Role of Spacer Length 586
Anna Cupani, Alessandro Moretto, Fernando Formaggio, Claudio TonioloExperimental and Theoretical Spectroscopy Study of 3-10-Helical PeptidesUsing lsotopic Labeling 588AhmedLakhani, Anjan Roy, Marcelo Nakaema, Matteo De Poli, FernandoFormaggio, Claudio Toniolo, Timothy A, KeiderlingOostatic Peptides Containing D-Amino Acids: Degradation, Accumulation inOvaries and NMR Study 590Jan Hlavdcek, B. Bennettova, B. Cerny, V. Vlasdkovd, J. Holik, M.
Budeslnsky, Jifina Slaninovd, R. TykvaDendrimeric Peptides with Affinity to Opioid Receptors - ComplexationStudies
592Marta Sowinska, Anna Lesniak, A. W. Lipkowski, Z. Urbanczyk-LipkowskaNMR-Based Conformational Studies of the C-Terminal
Heptadecapeptide(101-117) of Human Cystatin C 594
Martyna Maszota, P. Czaplewska, A. Sladewska, M. Spodzieja, J. Ciarkowski
Beta-Aspartic Acid Impairs the Ability to Bind Metal Ions by Immunosup-presory Fragment of Ubiquitin and Other Peptides As Studied by ESI-MS/MS 596
Marek Cebrat, Marlena Zajaczkowska, Piotr Stefanowicz, Zbigniew SzewczukEnsemble Fit of Conformational Equilibria ofRestrained Peptides to NMRData. Dependence on Force Fields: Amber8 Vs ECEPP/3 598
Jerzy Ciarkowski, S. Luczak, M. Oleszczuk, J. WojcikUnderstanding and Modulation ofthe Folding of a Helix-Loop-HelixDimerization Domain 600Michael Beisswenger, Sara Pellegrino, Roberto Fanelli, Nicola Ferri, MariaL. Gelmi, Chiara Cabrele
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2D IR Spectroscopy of Oligopeptides Conformationally Restrained by Ca,a-
Di alkylated Glycyl Residues 602
Hiroaki Maekawa, Matteo De Poll, Gema Ballano, Fernando Formaggio,Claudio Toniolo, Nien-Hui Ge
In Vitro Antiviral Properties ofAlloferon, Any-GS and Their AnaloguesAgainst Human Herpes Virus and Coxsackie B2 Virus 604
M. Kuczer, A. Midak-Siewirska, R. Zahorska, M. Luczak, D. Konopinska
Novel Calpain Inhibitors 606
Zoltdn Banoczi, Levente E. Ddkus, Agnes Tantos, Attila Farkas, Peter Tompa,Peter Friedrich, Ferenc Hudecz
PNA-Peptide Conjugates for Regulation ofDNA and RNA G-QuadruplexStructures Depending on a Particular Protease Concentration 608
Kenji Usui, Keita Kobctyashi, Naoki Sugimoto
Structure ofa New Stable Cu(III)/Cyclopeptide Complex by Cu K-Edge XAS