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How to Use This Book | |
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The Subject | |
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The Aim | |
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The Approach | |
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The Topics | |
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Be Selective | |
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To Learn, or to Understand? | |
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Conventions Regarding Acids, Bases, and Ions | |
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Some Common Abbreviations | |
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Further Reading | |
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Secondary Metabolism: the Building Blocks and Construction Mechanisms | |
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Primary and Secondary Metabolism | |
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The Building Blocks | |
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The Construction Mechanisms | |
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Alkylation Reactions: Nucleophilic Substitution | |
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Alkylation Reactions: Electrophilic Addition | |
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Wagner-Meerwein Rearrangements | |
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Aldol and Claisen Reactions | |
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Schiff Base Formation and the Mannich Reaction | |
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Transamination | |
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Decarboxylation Reactions | |
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Oxidation and Reduction Reactions | |
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Dehydrogenases | |
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Oxidases | |
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Mono-oxygenases | |
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Dioxygenases | |
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Amine Oxidases | |
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Baeyer-Villiger Oxidations | |
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Phenolic Oxidative Coupling | |
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Glycosylation Reactions | |
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Some Vitamins Associated with the Construction Mechanisms | |
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Vitamin B[subscript 1], Vitamin B[subscript 2], Vitamin B[subscript 5], Vitamin B[subscript 6], Vitamin B[subscript 12], Vitamin H | |
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Further Reading | |
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The Acetate Pathway: Fatty Acids and Polyketides | |
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Saturated Fatty Acids | |
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Unsaturated Fatty Acids | |
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Evening Primrose Oil | |
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Acetylenic Fatty Acids | |
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Branched-Chain Fatty Acids | |
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Prostaglandins | |
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Prostaglandins | |
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Thromboxanes | |
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Thromboxanes | |
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Leukotrienes | |
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Leukotrienes | |
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Aromatic Polyketides | |
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Cyclization: Simple Phenols | |
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Structural Modifications: Anthraquinones | |
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Senna, Cascara, Frangula, Allied Drugs | |
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C-Alkylation Reactions | |
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Mycophenolic Acid, Khellin and Cromoglycate | |
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Phenolic Oxidative Coupling | |
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Griseofulvin | |
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Oxidative Cleavage of Aromatic Rings | |
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Starter Groups other than Acetate | |
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Poison Ivy and Poison Oak, Aflatoxins, Cannabis, Tetracyclines, Anthracycline Antibiotics | |
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Extender Groups other than Malonate: Macrolides and Polyethers | |
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Macrolide Antibiotics, Avermectins, Polyene Antifungals, Tacrolimus and Sirolimus, Ansa Macrolides | |
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Cyclization through Diels-Alder Reactions | |
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Mevastatin and other Statins | |
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Further Reading | |
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The Shikimate Pathway: Aromatic Amino Acids and Phenylpropanoids | |
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Aromatic Amino Acids and Simple Benzoic Acids | |
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Folic Acid (Vitamin B[subscript 9]), Chloramphenicol | |
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Cinnamic Acids | |
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Lignans and Lignin | |
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Podophyllum | |
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Phenylpropenes | |
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Benzoic Acids from C[subscript 6]C[subscript 3] Compounds | |
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Coumarins | |
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Dicoumarol and Warfarin, Psoralens | |
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Flavonoids | |
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Flavonolignans | |
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Silybum marianum | |
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Isoflavonoids | |
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Derris and Lonchocarpus | |
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Terpenoid Quinones | |
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Vitamin E, Vitamin K | |
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Further Reading | |
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The Mevalonate Pathway: Terpenoids and Steroids | |
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Hemiterpenes (C[subscript 5]) | |
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Monoterpenes (C[subscript 10]) | |
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Irregular Monoterpenes | |
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Pyrethrins | |
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Iridoids (C[subscript 10]) | |
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Valerian | |
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Sesquiterpenes (C[subscript 15]) | |
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Feverfew, Camomile and Matricaria, Artemisia annua and Artemisinin, Gossypol, Trichothecenes | |
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Diterpenes (C[subscript 20]) | |
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Taxus brevifolia and Taxol (Paclitaxel), Ginkgo biloba, Forskolin | |
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Sesterterpenes (C[subscript 25]) | |
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Triterpenes (C[subscript 30]) | |
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Triterpenoid Saponins | |
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Liquorice, Quillaia, Ginseng | |
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Modified Triterpenoids | |
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Tetraterpenes (C[subscript 40]) | |
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Vitamin A | |
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Higher Terpenoids | |
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Steroids | |
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Stereochemistry | |
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Cholesterol | |
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Cholesterol | |
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Steroidal Saponins | |
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Dioscorea, Fenugreek, Sisal, Sarsaparilla, Yucca | |
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Cardioactive Glycosides | |
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Digitalis purpurea, Digitalis lanata, Strophanthus, Convallaria, Squill, Toxic Plants | |
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Phytosterols | |
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Soya Bean Sterols, Fusidic Acid | |
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Vitamin D | |
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Vitamin D | |
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Ecdysones and Brassinosteroids | |
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Bile Acids | |
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Bile Acids | |
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Adrenocortical Hormones/Corticosteroids | |
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Semi-synthesis of Corticosteroids | |
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Corticosteroid Drugs | |
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Progestogens | |
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Progestogen Drugs | |
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Oestrogens | |
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Oestrogen Drugs, Aromatase Inhibitors | |
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Androgens | |
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Androgen Drugs | |
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Further Reading | |
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Alkaloids | |
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Alkaloids Derived from Ornithine | |
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Pyrrolidine and Tropane Alkaloids | |
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Belladonna, Stramonium, Hyoscyamus, Duboisia, Allied Drugs, Hyoscyamine, Hyoscine, and Atropine, Coca | |
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Pyrrolizidine Alkaloids | |
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Alkaloids Derived from Lysine | |
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Piperidine Alkaloids | |
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Lobelia | |
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Quinolizidine Alkaloids | |
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Indolizidine Alkaloids | |
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Alkaloids Derived from Nicotinic Acid | |
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Pyridine Alkaloids | |
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Vitamin B[subscript 3], Tobacco, Areca | |
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Alkaloids Derived from Tyrosine | |
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Phenylethylamines and Simple Tetrahydroisoquinoline Alkaloids | |
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Catecholamines, Lophophora, Curare | |
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Modified Benzyltetrahydroisoquinoline Alkaloids | |
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Opium | |
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Phenethylisoquinoline Alkaloids | |
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Colchicum | |
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Terpenoid Tetrahydroisoquinoline Alkaloids | |
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Ipecacuanha | |
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Alkaloids Derived from Tryptophan | |
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Simple Indole Alkaloids | |
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Psilocybe | |
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Simple [beta]-Carboline Alkaloids | |
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Terpenoid Indole Alkaloids | |
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Rauwolfia, Catharanthus, Nux-vomica, Ellipticine | |
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Quinoline Alkaloids | |
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Cinchona, Camptothecin | |
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Pyrroloindole Alkaloids | |
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Physostigma | |
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Ergot Alkaloids | |
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Ergot, Morning Glories | |
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Alkaloids Derived from Anthranilic Acid | |
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Quinazoline Alkaloids | |
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Quinoline and Acridine Alkaloids | |
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Alkaloids Derived from Histidine | |
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Imidazole Alkaloids | |
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Pilocarpus | |
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Alkaloids Derived by Amination Reactions | |
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Acetate-derived Alkaloids | |
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Conium maculatum | |
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Phenylalanine-derived Alkaloids | |
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Ephedra, Khat | |
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Terpenoid Alkaloids | |
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Aconite | |
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Steroidal Alkaloids | |
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Solanum alkaloids | |
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Purine Alkaloids | |
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Caffeine, Theobromine, and Theophylline, Coffee, Tea, Cola, Cocoa, Mate tea, Guarana | |
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Saxitoxin and Tetrodotoxin | |
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Saxitoxin, Tetrodotoxin | |
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Further Reading | |
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Peptides, Proteins, and Other Amino Acid Derivatives | |
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Peptides and Proteins | |
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Ribosomal Peptide Biosynthesis | |
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Peptide Hormones | |
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Thyroid Hormones | |
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Thyroxine, Calcitonin | |
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Hypothalamic Hormones | |
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Thyrotrophin-releasing Hormone, Luteinizing-hormone-releasing Hormone, Growth-hormone-releasing Hormone/Factor, Somatostatin | |
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Anterior Pituitary Hormones | |
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Corticotrophin, Growth Hormone, Gonadotrophins | |
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Posterior Pituitary Hormones | |
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Oxytocin, Vasopressin | |
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Pancreatic Hormones | |
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Insulin, Glucagon | |
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Interferons | |
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Interferons | |
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Opioid Peptides | |
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Enzymes | |
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Multi-enzyme Peptide Biosynthesis | |
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Peptide Antibiotics | |
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Cycloserine, Polymyxins, Bacitracins, Tyrothricin and gramicidins, Capreomycin, Vancomycin and Teicoplanin, Bleomycin, Cyclosporins, Dactinomycin | |
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Peptide Toxins | |
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Death Cap (Amanita phalloides), Ricin, Botulinum toxin, Microcystins, Snake Venoms | |
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Modified Peptides: Penicillins, Cephalosporins and Other [beta]-Lactams | |
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Penicillins | |
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Penicillins | |
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Cephalosporins | |
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Cephalosporins, Cephamycins | |
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Other [beta]-Lactams | |
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Clavulanic Acid, Carbapenems, Monobactams | |
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Cyanogenic Glycosides | |
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Glucosinolates | |
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Cysteine Sulphoxides | |
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Garlic | |
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Further Reading | |
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Carbohydrates | |
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Monosaccharides | |
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Oligosaccharides | |
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Monosaccharides and Disaccharides | |
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Polysaccharides | |
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Polysaccharides | |
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Amino Sugars | |
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Aminoglycosides | |
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Aminoglycoside Antibiotics, Streptamine-containing Antibiotics, 2-Deoxystreptamine-containing Antibiotics, Lincomycin and Clindamycin | |
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Further Reading | |
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Index | |