I Introduction.- II Protecting Groups.- 1 Introduction of Amine Protecting Groups.- 2 Blocking of the ?-Carboxyl Group.- 3 Protection of Side Chain Functions.- III Activation and Coupling.- 1 The Acid Chloride Procedure.- 2 The Azide Process.- 3 Symmetrical Anhydrides.- 4 Mixed Anhydrides.- 5 Preparation of Active Esters.- 6 Coupling with Active Esters.- 7 Peptide Bond Formation with the Aid of Coupling Reagents.- IV Removal of Protecting Groups.- 1 Hydrogenation.- 2 Reduction with Sodium in Liquid Ammonia.- 3 Removal of the Phthalyl (Phthaloyl) Group by Hydrazinolysis.- 4 Acidolysis.- 5 Hydrolysis.- 6 Base Catalyzed Elimination.- 7 Nucleophilic Displacement.- 8 Iodolysis.- 9 Reduction of Methionine Sulfoxide Containing Peptides.- V Special Procedures.- 1 Ammonolysis of Esters.- 2 Transesterification.- 3 Cyclization.- 4 Polycondensation.- 5 Partial Synthesis.- VI Models for the Study of Racemization.- 1 Benzoyl-leucyl-glycine Ethyl Ester.- 2 The Anderson-Callahan Test.- 3 Acylation with Acetyl-l-isoleucine.- 4 The Izumiya-Muraoka Model.- 5 Synthesis and Enantioselective Enzymic Hydrolysis of Tetraalanine.- VII Reagents for Peptide Synthesis.- 1 tert-Butyl Azidoformate.- 2 1-Adamantyl Chlorocarbonate.- 3 1-Isobutyloxycarbonyl-2-isobutyloxy-1,2-dihydroquinoline (IIDQ).- 4 Diphenyl Phosphorazidate (Diphenylphosphoryl Azide, DPPA).- 5 3-Hydroxy-3,4-dihydroquinazoline-4-one (4-Hydroxyquinazoline 3-oxide).- 6 1-Hydroxybenzotriazole.- 7 Ethyl 2-hydroximino-2-cyanoacetate.- 8 1-Guanyl-3,5-dimethyl-pyrazole Nitrate.- VIII Appendix.- 1 Conversion of Dicyclohexylammonium Salts of Protected Amino Acids to the Free Acids.- 2 Preparation pf Analytical Samples.
