The Chemistry of Polypeptides

1 The Scientific Work of Leonidas Zervas.- 2 Active Esters and the Strategy of Peptide Synthesis.- I. Introduction.- II. The Development of Active Esters.- III. Active Esters in Stepwise Syntheses.- IV. Active Esters in Solid-Phase Peptide Synthesis.- V. Conclusions.- References.- 3 The Facilitation of Peptide Synthesis by the Use of Picolyl Esters.- I. Introduction : The “Functional Handle”.- II. 4-Picolyl Esters of ?-Amino Acids.- III. Use of 4-Picolyl Esters for the Facilitation of Peptide Synthesis.- IV. Conclusions from Recent Experience.- References.- 4 On Cysteine and Cystine Peptides.- I. Introduction.- II. S-Protection of Cysteine During Peptide Synthesis: Transformation of S-Protected Cysteine Peptides to Cystine Peptides.- III. Unsymmetrical Cystine Peptides.- References.- 5 The Tosyl and Related Protecting Groups in Amino Acid and Peptide Chemistry.- I. Introduction.- II. Introduction of Tosyl Groups.- III. General Properties of Tosylamino Acids.- IV. Removal of Tosyl and Related Protecting Groups.- V. Tosylamino Groups in Carboxyl Protection and Carboxyl Activation.- VI. Tosyl Derivatives in Amino Acid Chemistry.- VII. Tosyl Protecting Groups in Peptide Synthesis.- VIII. Analytical Uses of Arenesulfonyl Derivatives.- IX. Sulfonyl Derivatives Other Than Tosyl.- X. Conclusion.- References.- 6 Tactics for Minimal Protection in Peptide Synthesis.- I. The Concept of the Minimal Use of Protecting Groups.- II. Indispensable Protection.- III. Conclusion.- References.- 7 Peptide Synthesis and the Specificity of Proteinases.- 8 Structural Studies of Naturally Occurring Cyclic Polypeptides at Rockefeller University.- 9 The Conformations of Cyclopeptides in Solution.- I. Introduction.- II. General Principles of Composite Physicochemical Study of the Solution Conformation of Cyclopeptides.- III. Cyclohexapeptides.- IV. Valinomycin.- V. Enniatins.- VI. Gramicidin S.- VII. Antamanide.- VIII. Conclusion.- References.- 10 Survey of the Synthetic Work in the Field of the Bacterial Cell Wall Peptides.- I. Introduction.- II. Stereospecific Preparation of Meso-diaminopimelic Acid Derivatives.- III. Synthesis of Meso-diaminopimelic Acid-Containing Peptide Subunits of the Escherichia coli Cell Wall Peptidoglycan.- IV. Synthesis of ?-Branched Isoglutaminyl and Lysyl Peptides of the Staphylococcus aureus Cell Wall Peptidoglycan.- V. Synthesis of Linear and ?-Branched Glutamyl and Lysyl Peptides of the Micrococcus lysodeikticus Cell Wall Peptidoglycan.- VI. Conclusions.- References.- 11 Intracellular Proteolysis and Its Demonstration with Synthetic and Natural Peptides and Proteins as Substrates.- I. Introduction.- II. The Concept of Proteolysis.- III. Synthetic Substrates for Protease Determinations.- IV. Autoproteolysis of Organs.- V. Qualitative and Quantitative Differentiation of Autoproteolysis by Use of Synthetic Substrates.- VI. Autoproteolysis of the Cell Components and Proteolytic Interactions Between Them.- VII. Proteolytic Enzyme Activity of Lysosomes Toward the Cell’s Own Cytosol Proteins in Comparison to Foreign Proteins and Synthetic Peptides.- VIII. Significance of Enzymatic Reductive Cleavage of Disulfide Bridges for Intracellular Proteolysis.- IX. Conclusions.- References.- 12 Synthesis of Human ACTH and Its Biologically Active Fragments.- I. Introduction.- II. Synthesis of Human ACTH.- III. Synthesis of Sequence Homologs of Corticotropins.- IV. Biological Activity of the Synthetic Peptide Fragments.- V. Conclusions.- References.- 13 Synthesis of Pure Polypeptide Hormones with Full Biological Activity.- I. Introduction.- II. Glucagon.- III. [15-Leucine]-Human Gastrin I.- IV. Secretin.- V. Concluding Remarks.- References.- 14 Neurohypophyseal Hormones : Old and New Slants on the Relationship of Chemical Structure to Biological Activity.- 15 Use of Polymeric Reagents in the Synthesis of Linear and Cyclic Peptides.- I. Introduction.- II. Polymeric Reagents and Their Potential Use in Organic Synthesis.- III. Polymeric Reagents in Peptide Synthesis.- IV. Use of Polymeric Active Esters of Blocked Amino Acids in Peptide Synthesis.- V. Polymer Condensing Agents.- VI. Cyclic Peptides.- VII. Concluding Remarks.- References.- 16 Solid-Phase Peptide Synthesis.- I. Introduction.- II. The Solid-Phase Idea.- III. Summary and Conclusions.- References.- 17 Monitoring in Solid-Phase Peptide Synthesis.- I. Introduction.- II. Monitoring of the Coupling Reaction.- III. Monitoring of the Deprotection Step.- IV. Discussion.- References.- 18 Need for Solid-Phase Thinking in Solid-Phase Synthesis.- I. Introduction.- II. The Nonsolid State of the Solid Phase.- III. The Solid-Phase Peptide.- IV. Solid-Phase Analysis.- V. Conclusions.- References.