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Informationen zum Autor Patrizia Diana is full Professor of Medicinal Chemistry at the University of Palermo. She is currently coordinator of the Medicinal and Biological Section of the Department of Science and Technology: Chemical, Biological, and Pharmaceutical (STEBICEF); and is a member of the Italian Chemical Society and International Society of Heterocyclic Chemistry. Girolamo Cirrincione is full Professor of Medicinal Chemistry at the University of Palermo. He is a member of the Drug Discovery Committee of the Pharmacology and Molecular Mechanisms (PAMM)Group of the European Organization for Research and Treatment of Cancer; the Italian Chemical Society, where he is currently serving as President of the Medicinal Chemistry Division; and the International Society of Heterocyclic Chemistry, where he served as vice president for 2004-05 Klappentext This book describes biosynthetic methods to synthesize heterocyclic compounds, offering a guide for the development of new drugs based on natural products. The authors explain the role of natural products in chemistry and their formation along with important analytical methods and techniques for working with heterocycles.* Covers methods and techniques: isotopic labelling, enzymes and mutants, and pathway identification* Provides a thorough resource of information specifically on heterocyclic natural products and their practical biosynthetic relevance* Explains the role of natural products in chemistry and their formation* Discusses gene cluster identification and the use of biogenetic engineering in pharmaceutical application Zusammenfassung This book describes biosynthetic methods to synthesize heterocyclic compounds, offering a guide for the development of new drugs based on natural products. The authors explain the role of natural products in chemistry and their formation along with important analytical methods and techniques for working with heterocycles.* Covers methods and techniques: isotopic labelling, enzymes and mutants, and pathway identification* Provides a thorough resource of information specifically on heterocyclic natural products and their practical biosynthetic relevance* Explains the role of natural products in chemistry and their formation* Discusses gene cluster identification and the use of biogenetic engineering in pharmaceutical application Inhaltsverzeichnis PREFACE xiii ACKNOWLEDGMENTS xv 1 Introduction 1 1.1 Natural Products: Primary and Secondary Metabolites 4 1.2 Common Reactions in Secondary Metabolites 6 1.2.1 Alkylations 6 1.2.2 Wagner-Meerwein Rearrangements 16 1.2.3 Aldol and Claisen Reactions 17 1.2.4 Schiff Base Formation and Mannich Reactions 23 1.2.5 Transaminations 25 1.2.6 Decarboxylations 26 1.2.7 Oxidation and Reduction Reactions 31 1.2.8 Dehalogenation/Halogenation Reactions 39 1.2.9 Glycosylation Reactions 46 References 48 2 Techniques for Biosynthesis 51 2.1 Isotopic Labeling 52 2.1.1 Stable Isotopes 52 2.1.2 Radioactive Isotopes 61 2.2 Gene Coding for Enzymes 62 2.3 Combinatorial Biosynthesis 63 References 70 3 Three-Membered Heterocyclic Rings and Their Fused Derivatives 73 3.1 Aziridines and Azirines 73 3.1.1 Azicemicins 73 3.1.2 Miraziridine 74 3.1.3 Maduropeptin 75 3.1.4 Azinomycins 79 3.1.5 Ficellomycin 87 3.1.6 Mitomycins 89 3.1.7 Azirinomycin and Related Azirines 101 3.2 Oxiranes and Oxirenes 104 3.2.1 Fosfomycin 104 3.2.2 AK HC and AF toxins 111 3.2.3 Cerulenin 117 3.2.4 Polyhydroxyalkanoates 118 3.2.5 Epoxyrollins 118 3.2.6 Asperlactone Aspyrone Asperline 121 3.2.7 Tajixanthone 129 3.2.8 Cyclomarin 133 3.2.9 Cyclopenin 139 3.2.10 Ovalicin...
