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Peptides Frontiers of Peptide Science: Proceedings of the Fifteenth American Peptide Symposium June 14–19, 1997, Nashville, Tennessee, U.S.A. PDF

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Peptides Frontiers of Peptide Science Peptides Frontiers of Peptide Science Proceedings of the Fifteenth American Peptide Symposium June 14-19, 1997, Nashville, Tennessee, U.S.A. Edited by James P. Tam Department ofMicrobiology and Immunology, Vanderbilt University Medical School, Nashville, Tennessee, U.S.A. and Pravin T. P. Kaumaya Departments ofOb/Gyn, Medical Biochemistry and Microbiology and The Comprehensive Cancer Center, The Ohio State University, Columbus, Ohio, U.S.A. KLUWER ACADEMIC PUBLISHERS NEW YORK, BOSTON, DORDRECHT, LONDON, MOSCOW (cid:72)(cid:37)(cid:82)(cid:82)(cid:78)(cid:3)(cid:44)(cid:54)(cid:37)(cid:49)(cid:29) (cid:19)(cid:16)(cid:22)(cid:19)(cid:25)(cid:16)(cid:23)(cid:25)(cid:27)62(cid:16)X (cid:51)(cid:85)(cid:76)(cid:81)(cid:87)(cid:3)(cid:44)(cid:54)(cid:37)(cid:49)(cid:29) (cid:19)(cid:16)7923-5160(cid:16)6 (cid:139)(cid:21)(cid:19)(cid:19)(cid:21)(cid:3)(cid:46)(cid:79)(cid:88)(cid:90)(cid:72)(cid:85)(cid:3)(cid:36)(cid:70)(cid:68)(cid:71)(cid:72)(cid:80)(cid:76)(cid:70)(cid:3)(cid:51)(cid:88)(cid:69)(cid:79)(cid:76)(cid:86)(cid:75)(cid:72)(cid:85)(cid:86) (cid:49)(cid:72)(cid:90)(cid:3)(cid:60)(cid:82)(cid:85)(cid:78)(cid:15)(cid:3)(cid:37)(cid:82)(cid:86)(cid:87)(cid:82)(cid:81)(cid:15)(cid:3)(cid:39)(cid:82)(cid:85)(cid:71)(cid:85)(cid:72)(cid:70)(cid:75)(cid:87)(cid:15)(cid:3)(cid:47)(cid:82)(cid:81)(cid:71)(cid:82)(cid:81)(cid:15)(cid:3)(cid:48)(cid:82)(cid:86)(cid:70)(cid:82)(cid:90) (cid:51)(cid:85)(cid:76)(cid:81)(cid:87)(cid:3)(cid:3)(cid:139)1999(cid:3)(cid:46)(cid:79)(cid:88)(cid:90)(cid:72)(cid:85)(cid:3)(cid:36)(cid:70)(cid:68)(cid:71)(cid:72)(cid:80)(cid:76)(cid:70)(cid:3)(cid:51)(cid:88)(cid:69)(cid:79)(cid:76)(cid:86)(cid:75)(cid:72)(cid:85)(cid:86) (cid:36)(cid:79)(cid:79)(cid:3)(cid:85)(cid:76)(cid:74)(cid:75)(cid:87)(cid:86)(cid:3)(cid:85)(cid:72)(cid:86)(cid:72)(cid:85)(cid:89)(cid:72)(cid:71) (cid:49)(cid:82)(cid:3)(cid:83)(cid:68)(cid:85)(cid:87)(cid:3)(cid:82)(cid:73)(cid:3)(cid:87)(cid:75)(cid:76)(cid:86)(cid:3)(cid:72)(cid:37)(cid:82)(cid:82)(cid:78)(cid:3)(cid:80)(cid:68)(cid:92)(cid:3)(cid:69)(cid:72)(cid:3)(cid:85)(cid:72)(cid:83)(cid:85)(cid:82)(cid:71)(cid:88)(cid:70)(cid:72)(cid:71)(cid:3)(cid:82)(cid:85)(cid:3)(cid:87)(cid:85)(cid:68)(cid:81)(cid:86)(cid:80)(cid:76)(cid:87)(cid:87)(cid:72)(cid:71)(cid:3)(cid:76)(cid:81)(cid:3)(cid:68)(cid:81)(cid:92)(cid:3)(cid:73)(cid:82)(cid:85)(cid:80)(cid:3)(cid:82)(cid:85)(cid:3)(cid:69)(cid:92)(cid:3)(cid:68)(cid:81)(cid:92)(cid:3)(cid:80)(cid:72)(cid:68)(cid:81)(cid:86)(cid:15)(cid:3)(cid:72)(cid:79)(cid:72)(cid:70)(cid:87)(cid:85)(cid:82)(cid:81)(cid:76)(cid:70)(cid:15) (cid:80)(cid:72)(cid:70)(cid:75)(cid:68)(cid:81)(cid:76)(cid:70)(cid:68)(cid:79)(cid:15)(cid:3)(cid:85)(cid:72)(cid:70)(cid:82)(cid:85)(cid:71)(cid:76)(cid:81)(cid:74)(cid:15)(cid:3)(cid:82)(cid:85)(cid:3)(cid:82)(cid:87)(cid:75)(cid:72)(cid:85)(cid:90)(cid:76)(cid:86)(cid:72)(cid:15)(cid:3)(cid:90)(cid:76)(cid:87)(cid:75)(cid:82)(cid:88)(cid:87)(cid:3)(cid:90)(cid:85)(cid:76)(cid:87)(cid:87)(cid:72)(cid:81)(cid:3)(cid:70)(cid:82)(cid:81)(cid:86)(cid:72)(cid:81)(cid:87)(cid:3)(cid:73)(cid:85)(cid:82)(cid:80)(cid:3)(cid:87)(cid:75)(cid:72)(cid:3)(cid:51)(cid:88)(cid:69)(cid:79)(cid:76)(cid:86)(cid:75)(cid:72)(cid:85) (cid:38)(cid:85)(cid:72)(cid:68)(cid:87)(cid:72)(cid:71)(cid:3)(cid:76)(cid:81)(cid:3)(cid:87)(cid:75)(cid:72)(cid:3)(cid:56)(cid:81)(cid:76)(cid:87)(cid:72)(cid:71)(cid:3)(cid:54)(cid:87)(cid:68)(cid:87)(cid:72)(cid:86)(cid:3)(cid:82)(cid:73)(cid:3)(cid:36)(cid:80)(cid:72)(cid:85)(cid:76)(cid:70)(cid:68) (cid:57)(cid:76)(cid:86)(cid:76)(cid:87)(cid:3)(cid:46)(cid:79)(cid:88)(cid:90)(cid:72)(cid:85)(cid:3)(cid:50)(cid:81)(cid:79)(cid:76)(cid:81)(cid:72)(cid:3)(cid:68)(cid:87)(cid:29)(cid:3)(cid:3) (cid:75)(cid:87)(cid:87)(cid:83)(cid:29)(cid:18)(cid:18)(cid:78)(cid:79)(cid:88)(cid:90)(cid:72)(cid:85)(cid:82)(cid:81)(cid:79)(cid:76)(cid:81)(cid:72)(cid:17)(cid:70)(cid:82)(cid:80) (cid:68)(cid:81)(cid:71)(cid:3)(cid:46)(cid:79)(cid:88)(cid:90)(cid:72)(cid:85)(cid:10)(cid:86)(cid:3)(cid:72)(cid:37)(cid:82)(cid:82)(cid:78)(cid:86)(cid:87)(cid:82)(cid:85)(cid:72)(cid:3)(cid:68)(cid:87)(cid:29) (cid:75)(cid:87)(cid:87)(cid:83)(cid:29)(cid:18)(cid:18)(cid:72)(cid:69)(cid:82)(cid:82)(cid:78)(cid:86)(cid:17)(cid:78)(cid:79)(cid:88)(cid:90)(cid:72)(cid:85)(cid:82)(cid:81)(cid:79)(cid:76)(cid:81)(cid:72)(cid:17)(cid:70)(cid:82)(cid:80) Contents Preface xliii Fifteenth American Peptide symposium Committees xlvi Acknowledgments - Benefactors, Sponsors,Donors, and Contributors xlviii The First Merrifield Award and Past Alan E. Pierce Awards 1 AmericanPeptide Symposia li 1997 Young Investigators Poster Competition Awards liii American Peptide Society Travel Grant Recipients liv Abbreviations lvi First Merrifield Award Lecture-Makineni Lecture Fifty Years of My Protein Synthesis 1 Shumpei Sakakibara Keynote Lecture “The timehascome,” the walrus said, “totalkofmanythings...” -Lewis 11 Carroll, Through the Looking Glass Ralph Hirschmann Session I. Peptide Diversity/Chemical Libraries Novel Conceptsforthe Synthesis ofCyclic Peptide Libraries 19 Lianshan Zhang andJamesP. Tam Combinatorics,PeptideMimetics, andCombizymes 22 Hyunsoo Han, AnthonyM. Vandersteen, andKimD. Janda Peptides asPrecursors intheSynthesis ofHeterocyclicPositional Scanning CombinatorialLibraries 25 Jean-PhilippeMeyer, John M. Ostresh,AdelNefzi, Vince T. Hamashin, Christa C. Schoner, MarcA. Giulianotti, AmyL. Hannah, andRichardA. Houghten vi Expanding MolecularDiversity with Pseudopeptides andMacrotorials: Synthesis, Characterization and Biological Activities of Macrocyclic Combinatorial Libraries 28 Arno F. Spatola, Yvon Crozet, Peteris Romanovskis, and David Vogel Solid Phase Synthesis of Peptidomimetics 31 J.P. Mayer, D. Bankaitis-Davis, G. Beaton, K. Bjergarde,J.J. Gaudino, B.A. Goodman, C.J.Herrera, D.M. Lenz, G.S. Lewis, C.M. Tarlton, and J. Zhang Determination of the Amino Acid Composition of the Bioactive Components in Peptide Libraries 34 ÁrpádFurka, Eugen Câmpian, Hans R. Tanner, and Hossain H. Saneii Backbone Amide Linker (BAL) for Solid-Phase Synthesis of 2,5- Piperazinediones (DKP), Useful Scaffolds for Combinatorial Chemistry 37 Fernando Albericio, Montse del Fresno, Ariadna Frieden, Miriam Royo, Jordi Alsina, Knud J. Jensen, Steven A. Kates, and George Barany Fluorescent Quenched Substrates for ProteinDisulfide Isomerase (PDI) Defined By the Use of Disulfide Bridge Containing Libraries 40 J.C. Spetzler, V. Westphal, J.R. Winther, andM. Meldal Solid Phase Synthesis of Cyclic Homodetic Peptide Libraries Utilizing a Novel Intraresin Chain Transfer 42 Michael L. Moore, Kenneth A. Newlander, Heidemarie Bryan, William M. Bryan, and William F. Huffman Analysis of O-And N-Linked Glycopeptide Libraries by MALDI-TOF MS: Application in Solid Phase Assays of Carbohydrate-Binding-Proteins 45 Phaedria M. St.Hilaire, Morten Meldal, and Klaus Bock Unsymmetrically Functionalized Polyamine Libraries by a Solid Phase Strategy Starting from their Symmetrical Polyamine-Counterparts 47 Gerardo Byk, Marc Frederic, and DanielScherman Development of DNA-Encoded Library Containing Backbone Cyclic Peptides on Glass Beads 49 Anna Balanov, Eran Hadas, and Ilana Cohen Introduction of Bulky Betidamino Acids in Thyrotropin Releasing Hormone (TRH) 51 Dean A. Kirby, Marvin C. Gershengorn, and Jean E. Rivier vii Combinatorial Libraries and Polyamines in the Battle against Third World Trypanosomes 53 Helen K. Smith and MarkBradley Hybrid Resin for Synthesis and Screening of Synthetic Peptide Libraries 55 Hoebert S. Hiemstra, Willemien E. Benckhuijsen, Wolfgang E. Rapp, and Jan W. Drijfhout Combinatorial Libraries: Equimolar Incorporation of Benzaldehyde Mixtures in Reductive Alkylation Reactions 57 John M. Ostresh, Christa C. Schoner, Marc A. Giulianotti, Michael J. Kurth, Barbara Dörner,andRichardA. Houghten Potential CancerVaccine: Anti-IdiotypeAntibodiesDeveloped fromAntigen Binding Peptides Bind to Human Breast Cancer Antigen 59 John Mark Carter, JudySingleton, Phoebe Strome, Cindy Coleman, and Vernon Alvarez Studying Receptor-Ligand Interactions Using Encoded Amino Acid Scanning 61 Julio A. Camarero,JoannaPavel, and Tom W. Muir A Double-Bond-Containing Angiotensin and Its Derivatization into Linear vs. Branched Analogs 63 Kun-hwa Hsieh and GarlandR. Marshall Synthesis and Application of Tyrosine Kinase Substrate Libraries 65 Song Zheng, Richard Cummings, Rose Cubbon, Young-Whan Park, Patricia Cameron, Patrick Griffin, and Jeffrey Hermes Encoding Schemes for Application with Polyethylene Glycol-Polystyrene Graft (PEG-PS) Supports in Solid-Phase Peptide and Small Molecule Synthesis 67 Steven A. Kates, Wade Hines, Michael A. Kelley, Paul Lynch, Fernando Albericio, and George Barany Use of Phage Display and Cellulose-Bound Peptide Libraries for the Identification of Urea Herbicide Binding Peptides 69 Ulrich Hoffmüller, Christine Rottenberger, Günter Wellnhofer, Leodevico L. Ilag, Jürgen Spindler, and Jens Schneider-Mergener High Affinity Binding Peptides for Phosphatase 71 Stefan Vetter and Holger Schmid Session II. De Novo Design of Peptides & Proteins Five Axioms for Protein Engineering: Keys for Understanding Protein Structure/Function? 75 Dan W. Urry viii Novel Collagen-Mimetic Structures 79 Elizabeth A. Jefferson, and Murray Goodman De Novo Design of Helical Coiled-Coils: the Effect on Stability of Amino Acid Substitution in the Hydrophobic Core 82 Kurt C. Wagschal, Brian Tripet, Pierre Lavigne, and Robert S. Hodges Towards Full Mimics of Antibodies: A 37-aa Miniprotein with Two Independent Activities 85 Antonello Pessi, Elisabetta Bianchi, Jaques Neyton, Eugenia Drakopolou, and Claudio Vita Optical Holographic Data Storage Using Peptides 88 RolfH. Berg, Palle H. Rasmussen, Soren Hvilsted, and P.S. Ramanujam Developing Synthetic Hemoprotein Mimetics: Design, Synthesis and Characterization of Heme-Peptide Conjugates 91 Angela Lombardi, Flavia Nastri, Luca D. D’Andrea, Ornella Maglio, GabriellaD’Auria, Carlo Pedone, and Vincenzo Pavone A Novel Class of Calmodulin Mimetics: De Novo Designed Proteins in Molecular Recognition 94 Angela Lombardi, Giovanna Ghirlanda, Laura Zaccaro, Vincenzo Pavone, and William F. DeGrado Non native Architectures in Protein Design: Four Helix Bundles as Locked- in Tertiary Fold 97 Marc Mathieu and Gabriele Tuchscherer Synthesis and In Vivo Pharmacological Profile of Dimeric HOE 140 Bradykinin antagonists 100 Muriel Amblard, Isabelle Daffix, Gilbert Bergé, Pierre Dodey, Didier Pruneau, Jean-Luc Paquet, Pierre Bélichard, Jean-Michel Luccarini, and Jean Martinez Conformations and Use of Beta-Amino Acid Residues 103 Isabella L. Karle Modular Design of Synthetic Redox and Light-Absorbing Proteins 106 Wolfgang Haehnel, Harald K. Rau, Heike Snigula, and Hugo Scheer Synthesis of Semicaged Ruthenium(II) Complexes of a Branched Peptide Containing ThreeBipyridine Ligands 108 Barney M. Bishop, Matthrew C. Foster, Richard W. Vachet, and Bruce W. Erickson ix Design of New Tentoxin Analogues: Study of the ATP-Synthase Catalytic Mechanism 110 Florine Cavelier, Christine Enjalbal, Jérôme Santolini, Francis Haraux, Claude Sigalat, Jean Verducci, and François André Investigation of conformational Properties of Calcium-binding Peptides in the Cell Adhesion Molecules 112 Wei Yang and Jenny J. Yang End Capping and Helix Stabilization in Short Peptides 114 Hemender K. Reddy, and Krishnan P. Nambiar Novel Disubstituted Amino Acids for Peptide Secondary Structure Control 116 Christopher L. Wysong, Muna K. Thalji, Thad A. Labbe, and Robert P. Hammer Design of Antimicrobial Peptides Based on Sequence Analogy and Amphipathicity 118 A. Tossi, C. Tarantino,N. Mitaritonna, G. Rocco, and D. Romeo Synthesis and Structural Characterization of the Ligand Binding Site of Macrophage Scavenger Receptor 120 Hironobu Hojo, Yoshiko Akamatsu, Yu Nakamura, Shunji Miki, Kiyoshi Yamauchi, and Masayoshi Kinoshita Enantiomeric Structural Libraries of Unnatural Peptides Which Bind DNA and Alter Enzymatic Activity 122 L.M. Martin, B-HHu, andC. Li Interplay of Hydrophobic and Electrostatics in Peptide-bilayer Interactions 124 Li-Ping Liu and Charles M. Deber An Investigation of Position 3 in Arginine Vasopressin (AVP) 126 M. Manning, S. Stoev, L.L. Cheng, A. Olma, W.A. Klis, W.H. Sawyer, N.C. Wo, and W.Y. Chan Design and Expression of Recombinant Rop Protein Analogs Which Have Metal Binding Ability 128 Takahisa Nakai, Osamu Odawara, Takemune Yasuda, and Nobutaka Tani Combination of Helix Peptides with Intercalator Anthracene for Reporting Peptide-DNA Interactions 130 Tsuyoshi Takahashi, Akihiko Ueno, and Hisakazu Mihara X Macrotorials: Concept and Synthetic Examples Using PTH(1-34) 132 Wanli Ma, Jeffrey A. Dodge, and Arno F. Spatola Metal Ion-induced Folding of a De Novo Designed (-Helical Coiled-coil 134 W.D. Kohn, C.M. Kay, andR.S. Hodges to Transitions of Peptides Caused by Hydrophobic Defects 136 Yuta Takahashi, Akihiko Ueno, and Hisakazu Mihara A Natural Motif Approach to Protein Folding andDesign 138 Daniel J. Butcher, M.Anna Kowalska, Song Li, Zhaowen Luo, Simei Shan, Zhixian Lu, Stefan Niewiarowski, and Ziwei Huang Engineering of a Cationic Coiled-Coil Protein Bearing RGD-Like Ligands on Proline-II Helical Spacers 140 Harold D. Graham Jr., Deborah M. John, and Bruce W. Erickson Conformational Comparison of Peptide Templates and Their Folding Enhancements on TASP 142 Zhenwei Miao, Guangzhong Tu, Xiaojie Xu, Riqing Zhang, and Youqi Tang Use of a Potent and Selective Highly Constrained Peptide Agonist to Design De Novo an Equally Potent and Selective Non-Peptide Mimetic for the Opioid Receptor 144 Victor J. Hruby, Subo Liao, Mark D. Shenderovich, Josue Alfaro-Lopez, Keiko Hosohata, Peg Davis, Frank Porreca, and Henry I. Yamamura Engineering of the Deltoid Protein: A Model for the Four Corners of Quadrin, a Square Octamer from the Hepatitis delta Antigen 146 Matthew J. Saderholm, Gopal K. Balachandran, Stanley M. Lemon, and Bruce W. Erickson Engineering of Helical Oligoproline Redox Assemblies That Undergo Photoinduced Electron Transfer 148 Cheryl A. Slate, Durwin R. Striplin, Robert A. Binstead, Thomas J. Meyer, and Bruce W. Erickson The Use of 5-tert-Butylproline to Study Nucleation of Polyproline Type I Conformation 150 Eric Beausoleil, and William D. Lubell Structure-Activity Relationships in Cyclic -Sheet Antibacterial Peptides 152 LeslieH. Kondejewski, MasoodJelokhani-Niaraki, RobertE.W. Hancock, and Robert S. Hodges

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