Biochemical and Pharmacological Investigations of Peripheral and Brain δ-Opiate Receptors Using Tyr-D-Thr-Gly- Phe-Leu-Thr, a New Fully Specific 6-Ligand

Chapters in this book

1. Frontmatter I
2. Preface V
3. Contents VII
4. European Peptide Committee and Programme Committee XXVII
5. Honorary Committee and Organizing Committee XXVIII
6. Previous European Peptide Symposia XXIX
7. List of Participants XXXI
8. In Memoriam, Emil Taschner XLIII
9. In Memoriam, Dieter Marquarding XLVII
10. In Memoriam, Erhard Gross XLIX
11. Plenary Lectures
12. Recent Developments in the Chemistry and Biology of Cyclic Peptides 1
13. Conformational Considerations in the Design of Highly Potent and Long-Acting Peptide Hormone Agonists and Antagonists 19
14. Semisynthesis of Proteins and Peptides 31
15. Further Application of the Aqueous-Organic Two-Phase Approach to Enzyme-Catalyzed Peptide-Synthesis 43
16. Interactions of Lipid Bilayers with Corticotropin, Dynorphin, and Enkephalin Peptides 55
17. Gramicidin A: From Structure Towards the Molecular Mechanism of Action 73
18. Structural Comparisons of Retroenantiomeric Cyclic Hexapeptides 91
19. Circular Dichroism and Conformation of Peptides Related to Oxytocin 103
20. Synthesis of Peptides
21. Methods of Protection
22. Adaptation of Side Reactions for Peptide Synthesis 117
23. A New Type of Reagents for the Liberation of free Amino Components 121
24. The Application of Recently Developed Amino Protecting Groups in Peptide Synthesis 125
25. Preparation of 4-Sulfobenzyl Esters and their Use in Peptide Synthesis 129
26. The 2-Chloroethyl Group for Carboxyl Protection in Peptide Synthesis 133
27. Some Properties of Amino Acid and Peptide Phenacyl Esters 137
28. Temporary Substitution of Asparagine by Aspartic Acid in the Synthesis of Peptide Segments of Vasoactive Intestinal Peptide (VIP) 141
29. Methods of Coupling
30. Recycling of Excess Peptides from Fragment Condensations with Carbonyldiimidazole/1-Hydroxybenzotriazole Activation 145
31. Fatty Acids as Additives Suppressing Racemization of Amino Acid Residues in Peptide Synthesis by the DCC Method 149
32. HPLC as a Tool for the Investigation of Peptide Bond Formation 153
33. Application of Phosphinic Acids to Peptide Synthesis 157
34. A Reinvestigation of the Mixed Anhydride Method 163
35. Do Acylamino Acid and Peptide Anhydrides Exist? 167
36. First Results with New Reagents for Peptide Coupling 171
37. Peptide Syntheses without Isolation of Intermediates Using Biphasic Solvent System 175
38. Some Applications of the Curtius Rearrangement 179
39. Heterodetic Bonds
40. A New Method for the Selective Synthesis of Unsymmetrical Cystine Peptides 183
41. A Controlled Synthesis of Cyclic Unsymmetrical Cystine Peptides Bearing Two S-S Bridges in the Ring 189
42. Synthesis of Cysteine and Cystine Containing Peptides through 3-0-[N-Benzyloxycarbony 1-S-Acetamidomethyl- Cysteinyl] -Hydroxy-2-Phenylindenone 195
43. Method of Cyclization of Carba Analogues of Oxytocin 199
44. Synthesis of Isopeptides of Lysine as Fundamental Structural Units of Clavicepamines 203
45. Synthesis of Leucine Enkephalin- and Aspartame Analogs Containing Thioamide Linkages at Specific Positions 207
46. Synthesis on Polymeric Supports
47. Synthetic Studies on the Cecropins 211
48. Improved Syntheses of Substance P and Analogues on a Phenolic Resin Support 215
49. Peptide Ionophores. Synthesis and Characterization of Cyclic Octa- and Decapeptides Containing Leucine and Proline 219
50. Histone Model Peptide Synthetized by Solid Phase Fragment Condensation 223
51. The Biomimetic Gel Phase Synthesis of the RNA-Polymerase II Inhibitor Peptide 6'-Deshydroxy-Amanullin 227
52. Methodological Studies on Gel Phase Synthesis of the Arginine-Rich Propeptide Extension of Proalbumin 233
53. Use of the Nbb-Resin and 4-Hydroxymethylphenoxymethyl- Resin in Solid Phase Peptide Synthesis 237
54. Comparative Syntheses of an Octapeptide Using Continuous Flow (Column) and Conventional Polyamide Solid Phase Methods 241
55. The Solid Phase Synthesis of Neurotensin and Related Peptides on Polydimethylacrylamide Resins 247
56. Liquid-Phase Synthesis of Biologically Active Peptides on Easily Detachable Poly(Ethylene Glycol) Supports 251
57. Synthesis of Individual Peptides
58. Synthesis of Tuftsin under HPLC Control 257
59. Synthesis of Tuftsin Analogs with Elongated Peptide Chain and a Possible Anticancer Activity 261
60. Synthesis of an IgG Fragment Decapeptide and Preliminary Evaluation of its Role on Phagocytosis Stimulation of Human Polymorphonuclear Leukocytes 265
61. Synthesis and Pharmacologic Characterization of Glucagon (1-21)-Peptide 269
62. The Synthesis of Peptides Related to Prothrombin 273
63. Total Synthesis of Neurotoxin II from the Central Asian Cobra (Naja naja oxiana) venom 277
64. Synthesis of Labelled Peptides
65. Catalytic Exchange Labelling of Peptides 285
66. Solid Phase Synthesis of Neurotensin Analogues Susceptible to Radiolabelling 289
67. Tritium Incorporation into Histidine by Direct Catalytic Exchange: Labelling of Gonadotropin Releasing Hormone and Analogs 293
68. The ³H-Labelling of Peptides by Reduction of Dehydroleucine 297
69. Analogues of [8-ArginineJ Vasopressin for Hormone Receptor Research 301
70. Synthesis of Peptides Containing Non-Coded Amino Acids
71. Synthetic Fragments of Bacterial Cell Walls. Physicochemical and Biological Properties 305
72. Synthesis of Analogues of Precursors of Bacterial Peptidoglycan 311
73. Synthesis of Peptides with α, β-Dehydroaminoacid Residue 315
74. Synthesis of Dehydro Amino Acids and Peptides 319
75. α-Hydroxymethylation of Peptides: A Synthetic Route to Peptides Containing α-Hydroxymethy1-Amino Acids 323
76. L- α-Aminoadipic Acid δ-N-Benzyloxycarbonylamide and its Use in Peptide Synthesis 327
77. Synthesis of ß-Homo-L-Proline Analogues of Peptide Hormones 331
78. Optically Active Neopentylglycine and its Applications in Peptide Chemistry 333
79. Monodisperse Conjugates of Catecholamines 337
80. Total Synthesis of Althiomycin 341
81. Peptide Tricyclic Thia-Cyclols from Linear Precursors 345
82. Semi-Synthesis
83. Synthesis of Cytochrome C-(66-104) Nonatriacontapeptide and Analogues 349
84. Cytochrome c̱ Semisynthesis Using Enzymic Resynthesis Techniques 353
85. Semisynthetic Analogs of Globomycin 357
86. Semisynthetic Studies on the Bovine Trypsin-Kallikrein Inhibitor 361
87. Synthesis of a Hybrid Chicken/Human Insulin 367
88. Semisyntheses of Insulin Analogues by Replacement of the Sequence Al-4 371
89. Synthesis of Peptides Using Enzymes
90. Enzymatic Peptide Synthesis 375
91. Amidation of Synthetic Peptides by Pituitary Enzyme: Specificity and Mechanism of the Reaction 381
92. Reaction Mechanism in Trypsin Catalyzed Synthesis of Human Insulin Studied by ¹⁷O-NMR Spectroscopy 387
93. Trypsin-Catalyzed Oligomerization of the Ala-Ala-Arg Tripeptide 395
94. Thermitase-Catalyzed Hydrolysis of the C-Terminal Ester Group of Protected Peptide Ester Derivatives 399
95. Reversibility of Tryptic Hydrolysis in a Model Nonapeptide Sequence 403
96. Synthesis and Characterization of α- and/or ε-Substituted Lysine Peptides 407
97. Purification, Characterization and Analytics
98. Isolation by Preparative HPLC and Characterization of Major Components after Cyclization of a Decapeptide 411
99. Separation of Basic, Hydrophilic Peptides by Reversed- Phase Ion-Pair Chromatography. III. A Progress Report 415
100. Pre-Column Derivatization in HPLC of Peptides 419
101. Fast Atom Bombardment Mass Spectrometry - a New Tool for Peptide Sequence Analysis 423
102. Progress Towards a Post-Synthetic Chiral Analysis of Peptides 431
103. Direct Peptide Sequencing after TLC on Silica Gel without Substance Elution 437
104. Structure-Activity Relations
105. Neurohypophyseal Hormones
106. Two Analogues of Oxytocin with Modified Proline Cyclic Structure 441
107. Synthesis of new Active and Highly Selective Analogues of Oxytocin and Arginine-Vasopressin 445
108. CNS - Active Vasopressin Analogues 449
109. Investigation of Position 2 and 3 of Vasopressins 453
110. Analogues of Neurohypophysial Hormones Containing a D-Amino Acid in Position 2 457
111. Penicillamine-Containing Analogues of Neurohypophysial Hormones 461
112. 9-Substituted Vasopressin Analogs with Substantial Antidiuretic Activity 465
113. Interactions of Deamino-6-Carba-0xytocin Analogues in Rat Kidney and Liver Membrane Systems 467
114. Opioid Peptides
115. Synthesis and Biological Activity of New Enkephalin Analogues 471
116. Biochemical and Pharmacological Investigations of Peripheral and Brain δ-Opiate Receptors Using Tyr-D-Thr-Gly- Phe-Leu-Thr, a New Fully Specific 6-Ligand 475
117. Double Opiate Peptides. A Hypothesis of Two Different Mechanisms of Opiate Actions 481
118. Synthesis and Activity of Kyotorphin and its Analogs 487
119. Opioid Activity of Synthetic "Small Demorphins" 495
120. Structure-Activity Relationship of Dermorphin 501
121. Structural Modifications of β-Casomorphin-5: Synthesis and Pharmacology 505
122. Substance P
123. Substance P: The "Yin-Yang" of Behavior? 511
124. Hydrophilic Analogs of Substance P: Introduction of Sugar Acids and Sulfonium Groups 517
125. Influence of the Methionine Sidechain on the Biological Activity of Substance P 521
126. Substance P Analogues Containing Para-Substituted Phenylalanine: Synthesis and Pharmacological Properties 527
127. Synthesis of Potent and Specific Antagonists of Substance P 531
128. Substance P: Inactivation in CNS, Enzymatically Resistant Analogue and Development of "Brain Selective" Agonist 535
129. Other Biologically Active Peptides
130. Some Pharmaceutical Aspects of Peptide Research 543
131. The Synthesis and Gonadotropic Activity of [D-Tle⁶, Pro-NH-Et⁹]LRF 551
132. The Role of N-Acyl Groups in the Inhibitory Activity of LH-RH Analogues 555
133. Gonadotropin Releasing Hormone and its Analogs Desensitize Pituitary GnRH Action 559
134. DSIP: Novel Developments in Structure-Functional Studies 563
135. The Active Centres of Gastrin and Cholecystokynin: Syntheses, Conformational Problems, Correlation between Chemical Structure and Biological Activity 569
136. What is the Minimum Active Centre of Gastrin? 577
137. Structure-Activity Relationships of Highly Potent and Specific Gctapeptide Analogues of Somatostatin 583
138. Photoreactive [Leu⁹]-a-MSH Derivatives for Receptor Labelling 589
139. Degradation of α-Melanotropin by the Enzymes of the Soluble Fraction of Rat Brain Homogenate 593
140. Solid Phase Synthesis of Amunine (CRF), Sauvagine and Two Urotensin I 597
141. Proctolin: Synthesis, Enzymatic Degradation and Effect on the Cyclic Nucleotide System 603
142. Phosphonopeptides, Novel Inhibitors of Bacterial Cell Wall Biosynthesis 607
143. Urinary Excretion of Biologically Active Peptides and/or Peptide-Like Material in Various Disorders 613
144. Inhibitors and Binding Studies
145. Synthesis and Properties of Peptide Ketones 617
146. Enkephalin Diazomethyl and Chloromethyl Ketones: Synthesis and Biological Activity 623
147. Use of Quantitative Lipophilicity Relationships for the Design of Renin Inhibitors 629
148. Specific Inhibitors of Renin 635
149. Anionic Inhibitors of Elastase 639
150. Inhibition of Thrombin with H- and Boc-D-Phe-Pro-Agm 643
151. Analogues of Chymostatin 649
152. Binding Studies of Glucagon Antagonists 653
153. Determination of the Toxic and Antigenic Sites of Peptide Snake Venom Short Neurotoxins 657
154. Design and Synthesis of Two Peptides as Models for the Antigenic Sites of the Toxin II of the Scorpion Androctonus australis Hector 663
155. Immunology Related Peptides
156. Chemical Approaches to Improve Immunoassays of Peptide Hormones 667
157. Antineoplastic and Immunogenic Effects of Tuftsin (Thr-Lys-Pro-Arg) and its Analogs 673
158. Synthesis and Biological Assays of Peptides from a Tuberculin-Active Protein 679
159. Synthesis and Immunoreactivity of Escherichia Coli Heat Stable Enterotoxins Analogs 683
160. Preparation and Antigenicity of the C-Terminal Fragments of Human Leukocyte Interferons α2 and α1 687
161. Immunological Properties of Hapten-Peptide Conjugates: The Effect of Size, Lipophilic Substituents and Haptenic Distance on Tolerogenicity and Anaphylactogenicity 693
162. Conformational Studies
163. Conformation: Model Peptides
164. Conformational Features of Alternating L, D Peptides 699
165. Conformation of Cyclic Hexapeptides Studied by the Modified Factor Analysis of Circular Dichroism Spectra 705
166. Conformational Energy Calculations of Heterodetic Cyclic Hexapeptides Related to Oxytocin Ring Moiety 709
167. Conformational Energy Analysis of Oxytocin Molecule 713
168. Conformational Analysis of Peptides Substrate of N-Glycosylation 717
169. Serine and ß-Folding 721
170. X-Ray Structure and Conformation in Solution of Peptides Containing α-Aminoisobutyric Acid Residues 725
171. Preferred Conformations of Host-Guest Peptides 729
172. Conformation: Biologically Active Peptides
173. Conformation Calculations and Biologically Active Conformations of Cyclopeptides 735
174. Peptaibol Antibiotics: A Study on the Helical Structure of Emerimicins 741
175. Conformational and Ionophoric Properties of Prolyl Containing Analogs of Valinomycin 745
176. Synthesis of the Postulated Calcium Binding Site I of Calmodulin and Binding Studies 751
177. X-Ray Structural Study of Ionophores of a Valinomycin Group 755
178. Conformational Studies on Gaba-Enkephalinamides 759
179. Conformational Studies of the "in vitro" Potent Opiate [D-Met², Trp⁴, Pro⁵] Enkephalinamide by Fluorescence and Theoretical Calculations 763
180. Configuration of the Azo Bridge in Azo-Enkephalin 767
181. Self-Association of Substance P and its C-Terminal Sequences 771
182. Spatial Structure of Bradykinin Potentiating Peptide BPP_9α 775
183. Guest-Host Relationship in Bradykinin Peptides 781
184. Importance of Residue 5 in Antiotensin II 785
185. Circular Dichroism Aids Interpretation of Structure- Activity Relationship of Somatostatin Analogs 789
186. The Conformational Equilibrium of the Peptide Hormone Somatostatin and some Analogues in Aqueous Solution 793
187. Application of Homonuclear and Heteronuclear Two-Dimensional NMR Spectroscopy to Cyclolinopeptide A (1) 797
188. Role of the N-Terminal Fragment on the Stability of the Porcine Pancreatic Secretory Tryps in Inhibitors (KAZAL) 801
189. Relationship between the Steric Structure of Insulin Derivatives and their Biological Activity 805
190. Studies of Hydrogen Bonding in Relation to Oxytocin Activity 809
191. Synthesis, Conformation and Interaction with a Decanucleotide of the Fragment (26-39) of the "Cro" Protein from Bacteriophage λ 815
192. Abbreviations 819
193. Subject Index 829
194. Authors' Index 841
195. Backmatter 847