PEPTIDES: Chemistry, Structure and Biology

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1 PEPTIDES: Chemistry, Structure and Biology Proceedings of the Fourth American Peptide Symposium Edited by r Roderich Walter Professor and Head Department of Physiology, University of Illinois at the Medical Center, Chicago, Illinois and Johannes Meienhofer Section Chief Chemical Research Department, Hoffmann-La Roche, Inc. Nutley, New Jersey ANN ARBOR SCIENCE PUBLISHERS INC P.O. BOX 1425 ANN ARBOR, MICH

2 TABLE OF CONTENTS SECTION I SCIENTIFIC PROGRAM IN TRIBUTE TO LYMAN C. CRAIG Lyman C. Craig, in Memoriam. 5. Moore 5 Structure and Function of Snake Venom Toxins. D. Eaker 17 Subtilin and Nisin: The Chemistry and Biology of Peptides with a,3-unsaturated Amino Acids. E. Gross. 31 Chemical Investigations of the Function of Hemoglobin from a Structural View. R. J. Hill, R. M. Macleod.. 43 Protein-Nucleic Acid Interactions. W. Konigsberg, E. Anderson, Y. Nahxshima 49 ; SECTION II CONFORMATIONAL STUDIES The State of the Art of X-Ray Crystallography of Peptides. I. L. Karle 61 A Crystallographic Study of Cyclo(Triprolyl): Flexibility of Prolyl Residues. M. E. Druyan, C. L. Coulter Conformational Flexibility of Cyclo(Triprolyl) in Solution - A Carbon-13 NMR Investigation. R. Deslauriers, I. C. P. Smith, M. Rothe 91 Conformational Mobility of Peptides as Evaluated from Spin-Lattice Relaxation Times of 13 C and 2 H. I. C. P. Smith, K. Sahaumburg, R. Deslauriers Utilization of Proton and Carbon-13 Magnetic Resonance in the Evaluation of Polypeptide Secondary Structure in Solution. D. W. Urry, M. M. Long, L. W. Mitchell, K. Ohmoto 113 vii

3 The Study of Peptides by INDOR, Difference NMR and Time-Resolved Double Resonance Techniques. W. A. Gibbons, D. Crepaux, J. Delayre, J. Dunand, H. Wyssbrod 127 Folded Conformations of Tetrapeptides in Hydrogen Bonding Solvents. D. K. Kopple, A. Go 139 The Relative Stabilities of the 3-Structures of Monodisperse Synthetic Linear Homo-Oligopeptides with Aliphatic Side Chains. C. Toniolo, G. M. Bonora The Solution Conformation of Bradykinin. V. T. Ivanov, M. P. Filatova, Z. Reissman, T. 0..Reutova, E. S. Efremov, V. S. Pashkov, S. G. Galakitbnov, G. L. Grigoryan, Yu. A. Ovahinnikov 151 Solvation of Angiotensin II and Gramicidin S Determined by NMR Solvent Saturation Method. T. P. Pitner, J. D. Gliakson, R. Rowan, J. Dadok, A. A. Bothner-By Conformational Studies on the Luteinizing Hormone Releasing Factor (LRF) and Related Compounds. B. Donzel, C. Gilon, D. Blagdon, M. Erisman, J. Burnier, M. Goodman, J. Rivier, M. Monahan 165 Physicochemical Characteristics and a Proposed Conformation of Somatostatin. L. A. Holladay, D. Puett NMR Conformational Studies of Actinomycins Containing Sarcosine in Place of Proline. A. B. Mauger Analyses of Cyclic Peptide Conformation by Lanthanide- Assisted NMR. P. E. Young, V. Madison, C.-H. Niu, E. R. Blout 187 Sandwich Complexing of Metal Binding Cyclopeptides and Its Biological Implications. V. T. Ivanov', L. A. Fonina, N. N. Uvarova, S. A. Koz 'min, T. B. Karapatnitskaya, N. M. Chekhlayeva, T. A. Balashova, Yu. A. Ovahinnikov C NMR Studies of Complexes Between Amino Acids and Cyclic Peptides. C. M. Deber, B. Bartman, E. R. Blout 203 Molecular Design of a Cyclic Octapeptide Mimicking the Zinc(II) Binding Site of Carboxypeptidase A. Theoretical Studies on the Conformation of the Designed Cyclic viii

4 Peptide-Zinc(II) Complex. V. Renugopalakrishnan, B. Sarkar.* Synthesis of a Cyclic Octapeptide Designed to Mimic the Zinc-Binding Site of a Carboxypeptidase A. K. S. N. Iyer, B. Sarkar 215 Conformational Studies on L,D-Alternating Polypeptides. F. Asaoli, P. De Santis, A. Pallesohi, R. Rizzo Resonance and Non-Resonance Raman Spectroscopy: A Probe of Peptide and Protein Conformation. H. E. Stanley, I. M. Asher, K. J. Rothschild, G. D. J. Phillies, E. B- Carew, R. Bansil, I. A. Michaels 227 A Novel Method for Conformational Analysis of Peptides in Oriented Polyoxyethylene by Infrared Dichroism. R. T. Ingwall, C. Gilon, M. Goodman 247 Conformational Properties of Oligopeptides Containing Two Aromatic Amino Acid Residues Separated by a Variable Distance. P. L. Luisi, R. Guarnaacia, V. Rizzo, G. P. Lorenzi, P. Wiget, P. Skrabal 255 The Influence of Short-Range Interactions in Peptides and Proteins. S. S. Zimmerman, H. A. Scheraga Dielectric Constant or Dielectric Function? E. Ralston, R. L. Somorajai 271 Conformational Calculations of Peptide Conformation: Synthesis of Quantum Mechanical and Empirical Approaches for Deriving Energy Functions. A. T. Eagler, A. Lapiccirella 279 Relationship Between Secondary Structure of Poly-a- Amino Acids and Planarity of the Peptide Group'. F. Fillaux, C. de Loz& 287 SECTION III SYNTHETIC STUDIES New Approaches to Peptide Synthesis. D. S. Kemp, D. Roberts, C. Hoyng, J. Grattan, F. Vellaccio, J. Reczek 295 ix

5 Peptide Synthesis from the Practitioner's Point of View. D. F. Veber 307 Application of the Additivity Principle for Prediction of Rate Constants in Peptide Chemistry. Further Studies on the Problem of ^.acemization of Peptide Active Esters. J. Kovaas, Rf Cover, G. Jham, Y. Hsieh, T. Kolas 317 Enzymes as Reagents in Peptide Synthesis. C. Meyers, J. D. Glass 325 New Urethane Protecting Groups: The Optically Active -1-Arylethoxycarbonyl Group. G. R. Matsueda, J. M. Stewart 333 TJie Use of Boron Tristrifluoro Acetate (BTFA) in the Synthesis of Biologically Active Peptides. W. Bauer, J. Pless 341 Comparison of p-nitrobenzyl and p-nitrophenyl Residues as Carboxyl Protecting Groups in the Synthesis of Oligopeptides. A. Raschig, E. Schaiah, F. Schneider a,3-unsaturated and Thioether Amino Acids in Peptide Synthesis. E. Gross, S. Matsuura 351 An Approach to the Synthesis of Dehydropeptides. C. H. Stammer, E. G. Breitholle 359 Application of a New Repetitive Method to the Synthesis of a Pentapeptide Sequence from Angiotensin II. J. Burton 365 The Mechanism of the Carbodiimide Reaction. IV. New Probes for the Study of Acylation Reactions. J. Rebek, D. Brown, S. Zimmerman 371 Preferential Acylation of 'Non-Hindered' Peptide Bonds. Acylation and Methanolysis as a Possible Means of Producing Fragment Peptides. 7. B. Angadi, J. S. Davies, K. H. Hopkins, R. K. Merrit 375 Synthesis of Serine-Containing Glycotripeptides. H.-G. Garg, R. W. Jeanloz 379

6 Linear and Cross-Linked Polymers as Chemical Reagents. H. Morawetz 385 Polymeric Reagents in Peptide Synthesis: Recent Developments. M. Fridkin, R. Kalir, A. Warshawsky, A. Patchornik 395 Solid Phase Peptide Synthesis by Oxidation- Reduction Condensation. R. Matsueda, H. Maruyama, E. Kitazawa, H. Takahagi, T. Mukaiyama 403 Quantitative Monitoring of the Redox Condensation of Ddz-Amino Acids in the Merrifield Synthesis of Secretin Sequences. C. Birr, M. Ueki, R. Frank 409 An Improved Polystyrene Support for Solid Phase Peptide Synthesis. J. T. Sparrow 419 Automatically Programmed Synthesizer for the Liquid Phase Synthesis. E. Bayer, M. Mutter, G. Holzer Combined Use of Soluble Supports and Solid Polymer Reagents for Peptide Synthesis. G. Jung, G. Bovermann, W. GOhring, G. Heusel 433 Investigation of Solid Supports and Carboxyl- Protecting Groups in Alternating Liquid-Solid Phase Peptide Synthesis. H. Frank, H. Meyer, H. Hagenmaier 439 B-Phenacyl Esters of Aspartyl Peptides to Minimize Succinimide Formation during HF Treatment. C. C. Yang, R. B. Merrifield 447 Side-Reactions of Glutamyl Peptides in Liquid Hydrogen Fluoride-Anisole Mixtures. R. S. Feinberg, R. B. Merrifield, with discussion by R. Hirschmann Large Scale Solid Phase Synthesis of ACTH. R. L. Colesaott, C. D. Bossinger, P. I. Cook, J. P. Dailey, T. Enkoji, E. Flanigan, J. E. Geever, C. M. Grogineky, E. Kaiser, B. Laken, W. A. Mason, D. B. Olson, H. C. Reynolds, M. 0. Skibbe 463 Large Scale Solid Phase Peptide Syntheses of Thyrotropin- Releasing Hormone and Luteinizing Hormone-Releasing Hormone. J. K. Chang, R. C. Meyers, D. Winkler, R. C. Orlowski 469 xi

7 SECTION IV BIOLOGICALLY ACTIVE PEPTIDES A New Route Towards the Synthesis of Human Insulin. B. Kamber, A. Hartmann, A. J'dhl, F. Mdrki, B. Riniker, W. Rittel, P. Sieber 477 Studies on the Synthesis of Ovine Insulin. R. G. Hiskey, A. Wittinghofer, A. N. Goud, R. R. Vunnam Ai-Bi-Crosslinked Insulins for Structure-Function and Reduction-Reoxidation Studies. D. Brandenburg, W. Schermutzki, A. Wollmer, H.-P. Vogt, J. Gliemann 497 Synthesis of the Docosapeptide Corresponding to the Entire Amino Acid Sequence of Porcine Motilin. H.- v Yajima, Y. Kai, H. Kawatani 503 Progress in the Synthesis of the Porcine Pancreatic Secretory Trypsin Inhibitor II (Kazal). R. Rocchi, C. A. Benassi, A. Guggi, R. Tomatis 509 Partial Synthesis of Proteins. Experiments Using Pancreatic Trypsin Inhibitor. D. F. Dyckes, R. C. Sheppard 515 Conformational Analysis of Growth Hormones and Synthesis of a Fragment of Human Growth Hormone. C. PSna, J. M. Stewart, A. C. Paladini, J. M. Dellacha, J. A. Santomt 523 Synthesis of Litorin. R. de Castiglione, F. Angelucchi 529 Molecular Pharmacology of Angiotensin II Receptors. K. J. Catt, S. Saltman, J. Douglas, A. Baukal, P. Fredlund i On the Selective Antagonism of Myotropic and Steroidogenic Activity of Angiotensin II. M. C. Khosla, R. R. Smeby, F. M. Bumpus 547 Cyclic Angiotensin. J. L. De Coen, E. Ralston, J. P. Duvieux, A. Loffet 553 Angiotensin as a Tool to Study Excitation-Contraction Coupling in Smooth Muscle. R. J. Freer 559 xii

8 Approaches to Mechanism of Smooth Muscle Action of Substance P, Eledoisin and Physalaemin, Using Their COOH-Terminal Sequences and Acyl Derivatives. H. Niedrich, J. Bergmann, M. Bienert, E. Albrecht, P. Oehme 565 Studies of Bio-Active Analogs of Parathyroid Hormone. D. Goltzman, E. N. Callahan, G. W. Tregear, J. T. Potts, Jr 571 N,N'-Diprotected a,<jj-aminoalkanoyl-lysine Dipeptide Bronchodilators. L. C. Dorman, R. H. Reitz, J. A. Krauss, R. C. Cheng, J. E. Lewis 579 Ovine Placental Lactogen: Structural and Functional Relationship with Primate Placental Lactogen, Growth Hormone, and Prolactin. T. Hurley, R. E. Fellows, W. Maurer, S. Handwerger 583 Pharmacological and Chemical Properties of Urotensin I and II Peptides from the Caudal Neurosecretory System of Bony Fish. G. Moore, A. Letter, K. Lederis The Mechanism of Lipid Binding by the Plasma Lipoproteins: Synthesis of Model Peptides. J. T. Sparrow, J. D. Morrisett, H. J. Pownall, R. L. Jackson, A. M. Gotto, Jr 597 Peptide Aldehyde Inhibitors of the Fibrinogen- Thrombin Reaction. S. Bajusz, E. Barabds, E. Szill, D. Bagdy 603 Biosynthesis of a-msh and ACTH. A. F. Bradbury, D. G. Smyth, C. R. Snell 609 Metabolism of Angiotensin in Vascular Smooth Muscle. D. Regoli, W. K. Park, F. Rioux, J. Magnan Hydrolysis and Cyclization of L-Aspartyl-L-Phenylalanine Methyl Ester in Blood Plasma in vitro. P. L. Fletcher, Jr., S. Moore 625 SECTION V BRAIN SPECIFIC PEPTIDES Pituitary Peptides and Memory. D. de Vied, B. Bohus, I. Urban, Tj. B. van Wimersma Greidanus, W. H. Gispen 635 xiii

9 GH-RIF, LH-RH, TRH, MIF-I, Substance P, and Angiotensin: Central Nervous System Studies. N. P. Plotnikoff, A. J. Kastin 645 Neuropeptides and Proteins. A. A. Galoyan 651 Sexual Arousal in Male Animals: A Central Effect of ACTH-Like Peptides in Mammals. A. Bertolini, W. Fratta, G. L. Gessa, G. P. Mereu, A. Tagliamonte, W. Ferrari 659 Purification of the Sleep-Promoting Substances from Sleep-Deprived Rat Brain. K. Uchizono, S. Inoue, M. Iriki, M. Ishikawa, Y. Komoda, H. Nagasaki 667 Learning-Induced Brain Peptides. G. Ungar, S. R. Burzynski, D. F. Tate 673 Structural Requirements for the Biological Activity of Neurotensin, A New Vasoactive Peptide. R. Carraway, S. Leeman 679 SECTION VI NEUROHYPOPHYSEAL HORMONES AND NEUROPHYSIN PROTEINS Dedicated to Dr. Josef Rudinger Remembering Josef Rudinger. J. S. Fruton 689 Membrane Effects of Neurohypophyseal Hormones and Related Studies with Parathyroid Hormone. I. L. Schwartz, W. N. Scott, R. Kinne, H. R. Wyssbrod, L. B. Roth, R. Walter 691 Interactions of Neurohypophyseal Hormonal Peptides with Isolated Rat Fat Cells. D. Bonne, P. Cohen Magnesium-Neurohypophyseal Hormone Interactions in Contraction of Arterial Smooth Muscle. B. M. Altura, B. T. Altura 719 A Simple Rapid and Quantitative in vitro Milk- Ejecting Assay for Neurohypophyseal Hormones and Analogs. V. J. Hruby, M. E. Hadley.729 The Design of Neurohypophyseal Peptides Possessing Selectively Enhanced and Inhibitory Properties. M. Manning, J. Lowbridge, W. H. Sawyer 737 xiv

10 Iodo and Tritio Derivatives of Neurohypophyseal Hormones. G. Flouret, S. Terada, T. Nakahara, S. H. Nakagawa, 0. Hechter 751 The Retention of Antioxytocic Activity by the Ring Moieties of [l-3-mercapto-0,3-diethylpropionic Acid] Oxytocin and [l-s-mercapto-3,3-pentamethylenepropionic Acid]Oxytocin. J. J. Nestor, Jr., M. F. Ferger, V. du Vigneaud 755 Degradation by Human Placental Tissue Extracts of Oxytocin Radioactively Labelled in Positions 2 or 9. W. B. Watkins, C. W. Small 761 Release of Melanocyte-Stimulating Hormone by Neurohypophyseal Hormone Fragments. M. E. Celis, S. H. Nakagawa, R. Walter 771 Effect of Pro-Leu-Gly-NH 2 and Tocinoic Acid on the Secretion of Melanocyte-Stimulating Hormone from Rat Pituitaries Incubated in vitro. A. Vivas, M. E. Celis 111 Free Solution Conformation of Neurohypophyseal Hormones. J. D. Gliakson 787 Conformational Studies of Neurohypophyseal Hormones and Inhibitors Using High Resolution NMR Spectroscopy. J.-P. Meraldi, D. Yamamoto, V. J. Hruby, A. I. R. Brewster 803 The g-turn in the Cyclic Moiety of Oxytocin: PMR Studies of [Pro^Gly 1 *] Oxytocin in Dimethylsulfoxide. H. R. Wyssbrod, A. Ballardin, W. A. Gibbons, J. Roy, I. L. Schwartz, R. Walter 815 Carbon-13 Nuclear Magnetic Resonance Studies of the Binding of Selectively 13 C-Enriched Oxytocin to its Neurohypophyseal Carrier Protein, Bovine Neurophysin II. J. H. Griffin, C. Di Bello, R. Alazard, E. Sala, P. Cohen..< ' Kinetics of Oxytocin Binding to Neurophysin Measured by Temperature-Jump Relaxation. A. F. Pearlmutter xv

11 SECTION VII HYPOTHALAMIC PEPTIDES Hypothalamic Hormones: A Fluid Story. W. F. White 841 Possibilities for the Dual Control Role of the Hypothalamic Peptides. J. G. Vassileva-Popova, V. Z. Sparrow 853 Synthesis of Somatostatin. P. Giori, M. Guarneri, C. A. Benassi 859 Luteinizing Hormone Releasing Factor and Somatostatin Analogs. J. Rivier, N. Ling, M. Monahan, C. Rivier, M. Brown, W. Vale 863 Structure-Activity Relationships in Luteinizing Hormone-Releasing Hormone. K. U. Prasad, R. W. Roeske, F. L. Weitl, J. A. Vilchez-Martinez, A. V. Sahally Structure-Activity Studies on Somatostatin. D. Sarantakis, W. A. McKinley, N. H. Grant 877 Structure-Function Relationships of LH-RH/FSH-RH. W. Kdnig, J. Sandow, R. Geiger 883 SECTION VIII ANTIBIOTICS, ENZYME INHIBITORS, AND TOXINS Structural and Mechanistic Studies of Antibiotics. C. H. Hassall 891 Interaction of Pepsin with Pepstatin. A. C. M. Paiva, A. Grandino 909 Conformation-Directed Proteolysis of Kunitz Bovine Trypsin Inhibitor. J. Chauvet, R. Acher 915 The Design of Effective Renin Inhibitors. J. Burton, E. Haber, K. Poulsen 921 Conformation and Biological Activities of the Toxic Cyclopeptides of Aminita Phalloides. H. Faulstich, Th. Wieland " 927 Synthesis and Conformational Studies of the Neurotoxins and Cytotoxins of Snake Venom. V. I. Tsetlin, I. I. Mikhaleva, M. A. Myagkova, L. B. Senyavina, A. S. Arseniev, V. T. Ivanov, Yu. A. Ovchinnikov 935 xvi

12 Synthesis of Cyclic Tetrapeptides Related to Tentoxin. D. H. Rich, P. Mathiaparanam, J. A. Grant, P. Bhatnagar 943 Solid Phase Synthesis of an Octadecapeptide with Full Apamin Activity. J. Van Rietschoten, C. Granier, H. Rochat, S. Lissitzky, F. Miranda 949 SECTION IX ANALYTICAL AND ISOLATION PROCEDURES High Performance Liquid Chromatography and Droplet J Countercurrent Chromatography in the Peptide Labora- ' tory. H. Yoshida, C. L. Zimmerman, J. J. Pisano ^ Colorimetric Amino Acid Analysis Using Fluorescamine. fy A. M. Felix, V. Toome, S. De Bernardo, M. Weigele (/\ Advances in Ultrasensitive Sequence Analysis of Peptides. H. D. Niall 975 The Use of Dipeptidyl Aminopeptidase (DAP) and Gas Chromatography-Mass Spectroscopy (GC-MS) in Polypeptide Sequencing. H. C. Krutzsch, J. J. Pisano Characterization of Putative Cyclotetra L-Alanine. W. L. Anderson, D. Balasubramanian, D. B. Wetlaufer Methodology and Application of Biospecific Affinity Chromatography. D. Cowburn, A. Fischman 997 Quantitative Affinity Chromatography and Its Application to Studies of Ligand Binding by Semisynthetic Ribonuclease-S' Analogues. J. M. Chaiken, H. C. Taylor 1013 LIST OF PARTICIPANTS 1021 ABBREVIATIONS 1029 CONTRIBUTORS 1032 SUBJECT INDEX 1033 AUTHOR INDEX 1049 xvii

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