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| About This Book, and How to Use It | |
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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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| Nomenclature | |
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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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| Fixed Oils and Fats, Evening Primrose Oil | |
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| Acetylenic Fatty Acids | |
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| Branched-Chain Fatty Acids | |
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| Echinacea | |
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| Prostaglandins | |
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| Prostaglandins, Isoprostanes | |
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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, Hypericum/St John's Wort | |
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| C-Alkylation Reactions | |
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| Mycophenolic Acid, Khellin and Cromoglicate | |
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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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| Macrolides and Polyethers | |
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| Extender Groups other than Malonate | |
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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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| Genetic Manipulation of the Acetate Pathway | |
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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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| Volatile Oils Containing Principally Aromatic Compounds | |
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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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| Styrylpyrones | |
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| Kava | |
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| Flavonoids and Stilbenes | |
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| Flavonolignans | |
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| Silybum marianum | |
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| Isoflavonoids | |
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| Phyto-oestrogens, 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 and Deoxyxylulose Phosphate Pathways: Terpenoids and Steroids | |
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| Hemiterpenes (C[subscript 5]) | |
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| Monoterpenes (C[subscript 10]) | |
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| Volatile Oils Containing Principally Terpenoid Compounds | |
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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, Chamomile 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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| 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, Oestrogen Receptor Antagonists | |
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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, Hyosycamus, 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, Areca, 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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| Amaryllidaceae Alkaloids | |
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| Galanthamine | |
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| Alkaloids Derived from Tryptophan | |
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| Simple Indole Alkaloids | |
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| 5-Hydroxytryptamine (Serotonin), Psilocybe | |
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| Simple [beta]-Carboline Alkaloids | |
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| Terpenoid Indole Alkaloids | |
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| Rauwolfia, Catharanthus, Iboga, 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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| Corticotropin, Growth Hormone, Prolactin, 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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| Nonribosomal Peptide Biosynthesis | |
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| Peptide Antibiotics | |
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| Cycloserine, Polymyxins, Bacitracins, Tyrothricin and Gramicidins, Capreomycin, Vancomycin and Teicoplanin, Bleomycin, Cyclosporins, Streptogramins, 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, Carbacephems | |
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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, Vitamin C | |
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| Polysaccharides | |
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| Polysaccharides | |
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| Aminosugars | |
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| Aminoglycosides | |
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| Aminoglycoside Antibiotics, Streptamine-containing Antibiotics, 2-Deoxystreptamine-containing Antibiotics, Acarbose, Lincomycin and Clindamycin | |
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| Further Reading | |
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| Index | |