Preparation of Homogeneous Insulin Tracers with Monoand Di-Iodo-Desaminotyrosines in Position B1

Chapters in this book

1. Frontmatter I
2. ACKNOWLEDGEMENTS VIII
3. Preface IX
4. CONTENTS XI
5. INTRODUCTION 1
6. SECTION I. STRUCTURE OF INSULIN
7. A Comparison Between the Insulin Molecules in 2-Zinc and 4-Zinc Insulin Crystals 9
8. Crystal Structure, Aggregation and Biological Potency of Beef Insulin Cross-Linked at A1 and B29 by Diaminosuberic Acid 17
9. Correlation of Structural Details of Insulin in the Crystal and in Solution 27
10. SECTION II. PEPTIDE SYNTHESIS
11. An Assessment of Protecting Group Strategies in Synthesis of Large Peptides 39
12. Fully Active Semisynthetic Insulin by Selective Formation of the Disulfide Bridges as an Intermediate Result of the Total Synthesis by Fragment Condensation on Polymer Phase 51
13. [A14-Phenylalanine-Insulin]: A Synthetic Analogue 59
14. [B25-Tyrosine]B-Chain-S-Sulfonate of Porcine Insulin 67
15. The Synthesis of [B25-4-Nitrophenylalanine]-Octapeptide B(23-30) of Porcine Insulin 73
16. A Novel Route for the Preparation of Mono-Iodotyrosine and Mono-Iodotyrosine-Containing Peptides by Electrochemical Reduction of Di-Iodo Derivatives 77
17. Alternative Approach for Human Proinsulin Synthesis 81
18. An Alternative Synthesis of Glucagon by the Method of Solid Phase Condensation of Peptide Fragments 91
19. SECTION III. SEMISYNTHESIS AND CHEMICAL MODIFICATION
20. Progress Towards the Semisynthesis of Preproinsulin 99
21. Specific Activation of the Arginine Carboxyl Group of the B-Chain of Bovine Des-Octapeptide-(B23-30)-Insulin 107
22. Enzyme-Catalyzed Semisynthesis with Insulin Derivatives 117
23. The Relative Reactivity of Insulin Amino Groups as an Indicator of Structural Accessibility and its Use for Synthetic Approaches for Structure-Function Studies 125
24. A14-(N-Methylpyridinium) and A14-(2-Nitro-4-Trimethylammoniophenyl) Derivatives of Bovine Insulin 135
25. Preparation of Covalent Insulin Dimers 143
26. Reactions of Insulin Derivatives with ETAC Reagents 151
27. SECTION IV. RADIOACTIVE LABELLING AND SEPARATION TECHNIQUES
28. The Application of HPLC to the Analysis of Radio- Iodinated Tracers of Glucagon and Insulin 161
29. Monoiodoinsulin Specifically Substituted in A14-Tyr or A19-Tyr 169
30. Preparation of Homogeneous Insulin Tracers with Monoand Di-Iodo-Desaminotyrosines in Position B1 177
31. Insulin and Proteins Labeled by Microwave Discharge Activation of Tritium 185
32. Radioactive Labelling (¹⁴ C, ³ H) of Insulin and Insulin Derivatives by Reductive Methylation; Isolation of Homogeneous N, N-Di-Methylated Derivatives 191
33. Quantitative Determination of Insulin by Gradient Elution HPLC 201
34. Some Preliminary Findings in Isotachophoretic Analyses of Insulin 207
35. Studies on the Denaturation of Dissolved Insulin 215
36. SECTION V. RECEPTORS AND HORMONE-RECEPTOR INTERACTION
37. ¹²⁵ I-SpHPP-Avidin: A Tool for Hormone Receptor Studies 225
38. Chromatographic Properties of the Adipocyte Transport System in Detergent Solution and its Resolution from the Insulin Receptor 233
39. Hydrophobic Interaction Chromatography as a Tool in Insulin Receptor Purification 243
40. Localization of Insulin-Receptor Complexes on the Surface of Whole Cells by Autoradiography 251
41. Insulin Receptors in the Heart Muscle: Evidence for the Negative Cooperativity Binding Model 259
42. Insulin Receptors, Insulin Degradation, and Biological Activity 263
43. Regulation of Insulin Receptors in Isolated Hepatocytes from Normal and Streptozotocin-Diabetic Rats in the Fed and 48 H Fasted State 271
44. Insulin-Receptor Turnover and Down Regulation 277
45. Receptor-Mediated Internalisation of Insulin, Glucagon and Growth Hormone in Intact Rat Liver. A Biochemical Study 285
46. Kinetics of Insulin Binding to Its Receptors in vivo. Effects of Fasting 293
47. Hystricomorph Insulins and Insulin Receptors 301
48. SECTION VI. PHOTO-INDUCED HORMONE-RECEPTOR COUPLING
49. Photoreactive Insulin Derivatives: Preparation and Characterization 309
50. Photoreactive Insulin Derivatives: Chemical and Physical Properties 317
51. The Preparation and Application of an A1-Substituted Photo-Reactive Insulin Analogue 327
52. Photoaffinity Labeling of Insulin Receptor Proteins of Liver Plasma Membranes 337
53. Characterisation of Insulin Binding Sites in Rat Liver Plasma Membranes Using Photoreactive Insulin Analogues 345
54. Permanent Activation of Lipogenesis by Insulin Covalently Bound to Adipocyte Receptors 353
55. SECTION VII. STRUCTURE, BINDING, ACTIVITY
56. The Activation of Adenylate Cyclase by Chemically Modified Forms of Glucagon and its Relationship to Receptor Binding 363
57. Structure-Activity Relationships of Insulin-Induced Negative Cooperativity Among Receptor Sites 371
58. Properties of a Mutant Insulin Species Causing Human Diabetes 393
59. A1-Modified Insulins: Receptor Binding and Biological Activity 403
60. Biological Activity of Insulin Analogues Substituted at the Amino Group of B1-Phenylalanine 409
61. Functional Role of the N-Terminal Region of the B-Chain of Insulin 417
62. Biological Properties of Covalent Insulin Dimers 425
63. Biological Activity and Receptor Binding of Six Different Covalent Dimers of Insulin 433
64. In vitro and in vivo Effects of Poly-N-Vinylpyrrolidone- Insulin 439
65. Study of Insulin Action by Use of Insulin-Dextran Complex: Uptake of Insulin into Subcellular Fractions and Stimulation of Pyruvate Dehydrogenase in Mouse Adipocytes 447
66. Studies on the Mechanism of Insulin Action VI: The Interaction of Insulin Fragments with Insulin Receptor 455
67. Stimulation of Intracellular H₂ 0₂ Production in Rat Epididymal Adipocytes by Insulin, Insulin Fragments, and Other Hormones and Growth Factors with Insulin-Like Activities 461
68. Early Events in Insulin Binding and Insulin Action in Fat Cells and Hepatocytes 469
69. Role of the Biodegradation Process in the Action of Insulin. A Proposal for a Model Consisting of Sulfhydryl- Disulfide Interchange Reaction and Proteolysis 475
70. Insulin Receptors, Receptor Antibodies and the Mechanism of Insulin Action 483
71. SECTION VIII. DEGRADATION
72. Studies on Uptake of [³ H]-Insulin by Erythrocytes 495
73. An Insulin-Degrading Enzyme from Human Erythrocytes: Isolation and Characterization 501
74. Comparison of ¹²⁵ I-Insulin and [B1- 3 H-Phenylalanine]- Insulin Degradation by Insulin Protease 509
75. The Chemical Characterization of the Products of the Processing of Subcutaneously Injected Insulin 517
76. Some Inhibitors of Insulin Degradation 525
77. Excretion of Endogenous and Exogenous Insulin by Kidney in Diabetic Ketoacidosis 531
78. Incubation of Insulin in Hyperglycemic Blood Generates Insulin Dimers 539
79. SECTION IX. IMMUNOLOGY
80. Genetic Regulation of the Immune Response of Mice to Insulins of Different Species 551
81. Genetic Control of the Immune Response to Insulin 559
82. Analysis of the Immunogenicity of Three Insulin- Preparations 569
83. Studies on the Immunological Properties of Natural and Modified Insulins 575
84. Genetic Control of the Immune Response to Insulin: A Clinical Study of Adverse Immunologic Reactions to Insulin 585
85. The Induction of Hyperglycemia with Insulin Antibodies to B-Chain Determinants 593
86. The Pattern of B-Lymphocyte Specificities for Modified and Unmodified Insulins in the Mouse 603
87. Specificity of Rabbit Anti-Insulin Antibody 611
88. Radioimmunoassay of Chemically-Modified Insulins - Use and Misuse 619
89. Purity of Chromatographycally Purified Insulins Measured by Skin-Reactivity and Insulin-Specific IGE 627
90. SECTION X. BIOSYNTHESIS, STORAGE, EVOLUTION
91. Human Preproinsulin: Primary Structure of the Messenger RNA 637
92. Quantification of Proinsulin Biosynthesis by Determination of Specific Radioactivity of [³ H]-Leucine in Pancreatic Islets 643
93. Immunoreactive Rat C-Peptides I and II in Glucose Perfusate of Isolated Pancreas 651
94. Biosynthesis of Somatostatin in Pancreatic Islets of Wistar Rats 659
95. Crystallography of Intracellular Insulin and Glucagon as Revealed by Investigations of Tissues and Models 665
96. Pancreatic Hormone Storage Granules: The Role of Metal Ions and Polypeptide Oligomers 673
97. On the Molecular Biology of Hagfish Insulin 683
98. SECTION XI. INSULIN-RELATED HORMONES
99. Possible Relationships in the Processing, Storage and Secretion of Some Insulin-Related Peptides 695
100. Insulin-Like Growth Factors 703
101. Relaxin and Relaxin-Like Peptides in Ovaries of Pregnant Sows and Sharks 709
102. Structural Studies on Porcine Relaxins and their Biosynthetic Precursors 719
103. PRESENTATIONS NOT INCLUDED IN THIS VOLUME 727
104. LIST OF PARTICIPANTS 729
105. ABBREVIATIONS 735
106. SUBJECT INDEX 739
107. AUTHOR INDEX 749