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Peptides for the New Millennium Co-Chairs of the 16Th American Peptide Symposium, Gregg B Peptides for the New Millennium Co-Chairs of the 16th American Peptide Symposium, Gregg B. Fields (left) and George Barany (right). Peptides for the New Millennium Proceedings of the 16th American Peptide Symposium June 26-July 1, 1999, Minneapolis, Minnesota, U.S.A. Edited by Gregg B. Fields Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, Florida, U.S.A. James P. Tam Department of Microbiology and Immunology, Vanderbilt University Medical School, Nashville, Tennessee, U.S.A. and George Barany Departments of Chemistry and Laboratory Medicine & Pathology, University of Minnesota, Minneapolis, Minnesota, U.S.A. KLUWER ACADEMIC PUBLISHERS NEW YORK, BOSTON, DORDRECHT, LONDON, MOSCOW H%RRN ,6%1 0-306-46881-6 3ULQW,6%1 0-792-36445-7 .OXZHU$FDGHPLF3XEOLVKHUV 1HZ <RUN%RVWRQ'RUGUHFKW/RQGRQ0RVFRZ 3ULQW 2000 Kluwer Academic Publishers $OOULJKWVUHVHUYHG 1RSDUWRIWKLVH%RRNPD\ EHUHSURGXFHG RUWUDQVPLWWHGLQ DQ\ IRUPRUE\ DQ\ PHDQV HOHFWURQLF PHFKDQLFDOUHFRUGLQJRURWKHUZLVHZLWKRXWZULWWHQFRQVHQWIURPWKH3XEOLVKHU &UHDWHGLQWKH8QLWHG6WDWHVRI$PHULFD 9LVLW.OXZHU2QOLQHDW KWWSNOXZHURQOLQHFRP DQG.OXZHU VH%RRNVWRUHDW KWWSHERRNVNOXZHURQOLQHFRP Contents Preface XXXV 16th American Peptide Symposium and American Peptide Society xliii Symposium Co-Chairs xliii Symposium Program Committee xliii Society Officers xliii Society Councilors xliii Society Honorary Members xliv Local Planning Committee xliv Focus Group Leaders xliv Local Staff xlv Local Volunteers xlvi Symposium Sponsors xlvii American Peptide Symposia li The Merrifield Award liii Vincent du Vigneaud Award lvii Ralph F. Hirschmann Award in Peptide Chemistry lviii American Peptide Society Travel Grants lix The Bruce W. Erickson Young Investigators’ Awards lxi The ESCOM Awards lxi Abbreviations lxiii The 1999 Merrifield Award / Rao Makineni Lecture 1 Mimetic peptides, demanding enzymes, and drug discovery 3 Daniel H. Rich Young Investigators’ MiniSymposium 17 Bruce W. Erickson: In memoriam 19 Arthur M. Felix Engineering of a cysteine-containing variant of quadrin, a protein containing the oligomerization site of the hepatitis delta antigen 20 Matthew J. Saderholm, Paul Saconn, Nimish Shah, and Bruce W. Erickson vi Characterization of betabellins 15D and 16D, designed beta-sandwich proteins that have amyloidogenic properties 22 Amareth Lim, Alexander M. Makhov, Lawreen H. Connors, Jeremy Bond, Hideyo Inouye, Jack D. Griffith, Daniel A. Kirschner, Catherine E. Costello, and Bruce W. Erickson Design and synthesis of inhibitors of botulinum neurotoxin A and B metalloproteases 24 Thorsten K. Oost, Chanokporn Sukonpan, and Daniel H. Rich Dimerization inhibitors of HIV-1 protease: Effective inhibition requires the cross-linking of non-identical peptides 26 Michael D. Shultz and Jean A. Chmielewski Backbone cyclic proteinomimetics derived from the arginine-rich domain of HIV-1 Tat and Rev proteins: One sequence, two conformations, two biological functions 28 Assaf Friedler, Nathan Luedtke, Dorit Friedler, Abraham Loyter, Yitzhak Tor, and Chaim Gilon Synthesis of several O-glycopeptide analogs of enkephalin 30 Scott A. Mitchell, Matthew R. Pratt, Victor J. Hruby, and Robin Polt Investigating the role of turns in the folding of a predominantly protein 32 Kenneth S. Rotondi, Kannan Gunasekaran, and Lila M. Gierasch Receptor-bound conformations of integrin antagonists by NMR spectroscopy 34 Elsa Locardi, Ralph-Heiko Mattern, Timothy I. Malaney, Daniel G. Mullen, Robert Minasyan, Michael D. Pierschbacher, and Murray Goodman Design, synthesis, and characterization of two core modules of bovine pancreatic trypsin inhibitor 36 Natalia Carulla, Clare Woodward, and George Barany The fine tuning of high affinity and selective non-peptide agonists of the receptor via solution and solid-phase 38 Josue Alfaro-Lopez, Toru Okayama, Keiko Hosohata, Peg Davis, Frank Porreca, Henry I. Yamamura, and Victor J. Hruby Cyclic dodecapeptides form ion channels in lipid bilayers 40 Dongxia Wang, Lili Guo, Patrick J. Edwards, Larry R. Jones, and Roger W. Roeske Synthesis and evaluation of potential affinity labels for opioid receptors 42 Heekyung Choi, Thomas F. Murray, and Jane V. Aldrich Synthetic Methodologies (including Large-Scale Synthesis) 45 Polyethyleneglycol-based chains of precise length for chemobodies 47 Keith Rose and Jean Vizzavona vii (Nsc) as an amino-protecting group and its application for peptide synthesis 50 Hack-Joo Kim and Vladmir V. Samukov Nsc- and Fmoc-amino acids for automated solid-phase peptide synthesis: Comparative study of the stability in various conditions 53 Yeon Sun Lee, Hyun Jin Lee, Doyoung Lee, and Hack-Joo Kim In situ generation of Fmoc amino acid chlorides for extremely difficult couplings to sterically hindered secondary amines in solid-phase peptide synthesis 55 Eliezer Falb, Tamar Yechezkel, Yosphe Salitra, Gary Gellerman, Dan Muller, and Chaim Gilon Evaluation of ivDde as a quasi-orthogonal protecting group for Fmoc solid-phase peptide synthesis 58 R. Randy Wilhelm, Ananth Srinivasan, and Michelle A. Schmidt (Nbs): A new protective group for the indole moiety of tryptophan 60 Aydar N. Sabirov, Vladimir V. Samukov, Pavel I. Pozdnyakov, and Hack-Joo Kim Practical asymmetric synthesis of glutamic acids 62 Vadim A. Soloshonok, Chaozhong Cai, and Victor J. Hruby Formation of substituted aromatic rings in amino acid systems via ruthenium activated reactions 64 Chris W. West, Jim W. Janetka, and Daniel H. Rich O-Acetyl-L-homoserine: A versatile synthon for the synthesis of L-homoserine peptides and 3-amino-2-pyrrolidinones 66 Guenter Knaup, Karlheinz Drauz, and Michael Schwarm Asymmetric synthesis of free unusual acid esters via C-C bond formation and simultaneous deprotection/purification 68 Guigen Li, Sun Hee Kim, Han-Xun Wei, Jason D. Hook, and Keith A. Fitzgerald High yield synthesis of heterocyclic alanine derivatives 70 Paula M.T. Ferreira, Hernâni LS. Maia, and Luís S. Monteiro Synthesis of (2S,4R) 4-aminoethyl-L-Pro and (2S,4R)-4-carboxymethyl-L-Pro from (2S,4R)- ester 72 Dewey G. McCafferty, Stephen L. Schneider, and Bruce W. Erickson A highly effective method for synthesis of arginines 74 Sotir Zakhariev, Zoltán Székely, Corrado Guarnaccia, Nikolinka Antcheva, and Sándor Pongor Diffusion phenomena and reactivity using polymer supports: A principal investigation 76 Wolfgang E. Rapp viii Solid-phase peptide synthesis in the direction 78 Nathalie Thieriet, Jordi Alsina, Francois Guibé, and Fernando Albericio Diisopropylethylamine salts for protected amino acids: Direct synthesis of peptides on solid-phase 80 Preeti Balse, Guoxia Han, Victor J. Hruby, and Lele Sun Synthesis of phosphorylated CRE BP1(19-106) amide using a phosphopeptide thioester prepared directly by an Fmoc solid-phase method 82 Saburo Aimoto, Koki Hasegawa, Xiangqun Li, and Toru Kawakami Preparation of phosphohistidyl peptides via oxidative coupling of H-phosphonates 84 Bennet J. Harding, W. Scott Dodson, Brian D. Bennett, William S. Marshall, and Mark A. Jarosinski Preparation and incorporation into small peptides and combinatorial libraries of phosphohistidine analogs for study of prokaryotic two-component signal transduction systems 86 Michael C. Pirrung, Sandra J. Drabik, Kurt V. Gothelf, Kenneth D. James, and Tao Pei Synthesis of phosphonamides and thiophosphonamides by a one-pot activation-coupling-oxidation protocol 89 Sheila D. Rushing and Robert P. Hammer Synthesis of phosphonopeptide and thiophosphonopeptide analogs as inhibitors of carboxypeptidase A 91 Hong Fan, Yuhong Zhao, Larry Byers, and Robert P. Hammer Application of solid-phase Ellman's reagent for preparation of disulfide-paired isomers of SI 94 Balazs Hargittai, Ioana Annis, and George Barany Alternative solid-phase reagents for formation of intramolecular sulfur-sulfur bridges in peptides under mild conditions 96 Ioana Annis and George Barany An evaluation of a novel safety catch linker for development of cyclic peptide libraries 98 G.T. Bourne, R.P. McGeary, S.W. Golding, W.D.F. Meutermans, P.F. Alewood, and M.L. Smythe Solid-phase synthesis of peptide aldehydes by a Backbone Amide Linker (BAL) strategy 100 Fanny Guillaumie, Nicholas M. Kelly, Joseph C. Kappel, George Barany, and Knud J. Jensen Backbone Amide Linker (BAL) methodology to accommodate C-terminal hindered, unreactive, and/or sensitive modifications 102 Jordi Alsina, T. Scott Yokum, Fernando Albericio, and George Barany ix A new tartaric acid-based linker for the synthesis of C-terminal peptide 104 Jean-Sébastien Fruchart, Cyrille Grandjean, Dominique Bonnet, Corinne Rommens, Hélène Gras-Masse, and Oleg Melnyk A new approach to the guanidinylation of peptides and peptidomimetics including aminoglycosides and related drugs 107 Tracy J. Baker and Murray Goodman Photoaffinity-labeled probes for the study of isoprenoid recognition sites 109 Tamara A. Kale and Mark D. Distefano Orthogonal methods for the synthesis of multiply labeled peptide probes and substrates 111 Michael F. Songster, Sara Biancalana, Ronald M. Cook, Daren J. Dick, and Derek Hudson Strategies for the synthesis of labeled peptides 113 Lisa Bibbs, Nicholas P. Ambulos, Steven A. Kates, Ashok Khatri, Katalin F. Medzihradszky, George Ösapay, and Susan T. Weintraub Orthogonal segment ligation 115 Zhenwei Miao, Qitao Yu, Yi-An Lu, Jin-Long Yang, Kalle Kaljuste, Chengwei Wu, Li Huang, and James P. Tam Use of orthogonal ligation methods for the synthesis of hetero peptide dendrimer 118 Chuan-Fa Liu, Chang Rao, and James P. Tam Minimization of side reactions during removal of the formyl protecting
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