Contents 23 CARBOHYDRATES AND NUCLEIC ACIDS 1097 23-1 Introduction 1097 23- Classification of Carbohydrates 1098 Monosaccharides 109 Epime 23. s:Side Re Base 1110 ides 112 23-10 Oxidation of mo 23-11 Nonreducing Sugars:Formation of Glyce 23-12 Ether and Ester Formation I117 23-13 Reactions with Phenylhydrazine:Osazone Formation 1119 23-14 Chain Shortening:The Rutf Degradation I120 23-15 Chain Lengthening:The Kiliani-Fischer Synthesis 1121 Summary:Reactions of Sugars 1122 23-16 Fischer's Proof of the Configuration of Glucose 1124 Determination of Ring Size:Periodic Acid Cleavage of Sugars 1127 Acids. ction 1137 e tides 1139 leic Acid 1141 23.23 and the Structur ckeic Acid 1141 23-24 Chapter 23 Glossary 1147 Study Problems 1140 24 AMINO ACIDS,PEPTIDES,AND PROTEINS 1153 24-1 Introduction 1153 d Su eochemisrry of the amino acids I54 24-3 Acid-Base Pronerties of Amino Acids 1158 24-4 Isoelectric Points and Electrophoresis 1160 24-5 Synthesis of Amino Acids 1161 Summary:Syntheses of Amino Acids 1166 Resolution of Amino Acids 116 24-7 Reactions of Amino Acids 1167 Summary:Reactions of Amino Acids 1170 248 Peptidesand Peptide Structure D Solid- de Synth 1188 2413 vels of otein 18 24-14 Protein Denaturation 1191 Chapter 24 Glossary 119 Study Problems 119623 CARBOHYDRATES AND NUCLEIC ACIDS 1097 23-1 Introduction 1097 23-2 Classification of Carbohydrates 1098 23-3 Monosaccharides 1099 23-4 Erythro and Threo Diastereomers 1102 23-5 Epimers 1103 23-6 Cyclic Structures of Monosaccharides 1104 23-7 Anomers of Monosaccharides; Mutarotation 1108 23-8 Reactions of Monosaccharides: Side Reactions in Base 1110 23-9 Reduction of Monosaccharides 1112 23-10 Oxidation of Monosaccharides; Reducing Sugars 1113 23-11 Nonreducing Sugars: Formation of Glycosides 1115 23-12 Ether and Ester Formation 1117 23-13 Reactions with Phenylhydrazine: Osazone Formation 1119 23-14 Chain Shortening: The Ruff Degradation 1120 23-15 Chain Lengthening: The Kiliani-Fischer Synthesis 1121 Summary: Reactions of Sugars 1122 23-16 Fischer's Proof of the Configuration of Glucose 1124 23-17 Determination of Ring Size; Periodic Acid Cleavage of Sugars 1127 23-18 Disaccharides 1129 23-19 Polysaccharides 1134 23-20 Nucleic Acids: Introduction 1137 23-21 Ribonucleosides and Ribonucleotides 1139 23-22 The Structure of Ribonucleic Acid 1141 23-23 Deoxyribose and the Structure of Deoxyribonucleic Acid 1141 23-24 Additional Functions of Nucleotides 1145 Chapter 23 Glossary 1147 Study Problems 1149 24 AMINO ACIDS, PEPTIDES, AND PROTEINS 1153 24-1 Introduction 1153 24-2 Structure and Stereochemistry of the a-Amino Acids 1154 24-3 Acid-Base Properties of Amino Acids 1158 24-4 Isoelectric Points and Electrophoresis 1160 24-5 Synthesis of Amino Acids 1161 Summary: Syntheses of Amino Acids 1166 24-6 Resolution of Amino Acids 1167 24-7 Reactions of Amino Acids 1167 Summary: Reactions of Amino Acids 1170 24-8 Structure and Nomenclature of Peptides and Proteins 1170 24-9 Peptide Structure Determination 1174 24-10 Solution-Phase Peptide Synthesis 1180 24-11 Solid-Phase Peptide Synthesis 1183 24-12 Classification of Proteins 1188 24-13 Levels of Protein Structure 1188 24-14 Protein Denaturation 1191 Chapter 24 Glossary 1193 Study Problems 1196 Contents xvii