The Biosynthesis of Secondary Metabolites

ISBN-13: 9780412277207 / Angielski / Miękka / 1989 / 232 str.

R. B. Herbert; Richard B. Herbert

Opis

The chief purpose of such new editions is to bring the text up to date. This I have tried to do. The danger with such endeavours is that the book becomes corpulent. This I have tried to avoid. In so doing I am evermore conscious of how much material has had to be omitted. As before the references (ca. 770 of them) which are cited are intended in part to provide the reader with access to material that has been omitted. I am deeply grateful to Mrs Marjorie Romanowicz for preparing the typed manuscript for this edition with customary accuracy and efficiency, to my wife Margaret for checking the references, and to research students Karl Cable, Lucy Hyatt, Mashupye Kgaphola and Andrew Knaggs for helping with the checking of the manuscript. Richard Herbert April 1988 Preface to the first edition This is a book about experiments and results of experiments. The results described are the fruit of thirty years' labour in the field of secondary metabolism. Secondary metabolism, more than any other part of the chemistry of life, has been the special preserve of organic chemists. Investigation of secondary metabolism began with curiosity about the structures of compounds isolated from natural sources, i.e. secondary metabolites. Coeval with structure determination there has been a curiosity about the origins and mechanism of formation of secondary metabolites (or natural products as they have been called). It is the experimental outcome of this curiosity that is described here.

Spis treści

1 Introduction.- 1.1 Primary and secondary metabolism.- 1.1.1 Introduction.- 1.1.2 Fatty acid biosynthesis.- 1.1.3 The biosynthesis of polyacetylenes and prostaglandins.- 1.2 Stereochemistry and biosynthesis.- 1.2.1 Chirality and prochirality.- 1.2.2 Chiral methyl groups.- 1.2.3 Hydroxylation at saturated carbon atoms.- 1.3 Some reactions of general importance in secondary metabolism.- 1.3.1 Oxidative coupling of phenols.- 1.3.2 Hydroxylation of aromatic substrates.- 1.3.3 Methylation.- References.- 2 Techniques for biosynthesis.- 2.1 Introduction.- 2.2 Isotopic labelling.- 2.2.1 Radioactive isotopes.- 2.2.2 Stable isotopes.- 2.3 Enzymes and mutants.- References.- 3 Polyketides.- 3.1 Introduction.- 3.2 Formation of poly-?-keto-acyl-CoA’s.- 3.2.1 Acetate and malonate.- 3.2.2 Assembly of poly-?-keto-acyl-CoA’s.- 3.3 Tetraketides.- 3.4 Pentaketides.- 3.5 Hexaketides.- 3.6 Heptaketides.- 3.7 Octaketides.- 3.8 Nona-and deca-ketides.- 3.9 Polyketides with mixed origins and large ring polyketides.- References.- 4 Terpenes and steroids.- 4.1 Introduction.- 4.2 Steroids.- 4.3 Pentacyclic triterpenes.- 4.4 Squalene.- 4.5 Monoterpenes.- 4.6 Sesquiterpenes.- 4.7 Diterpenes.- 4.8 Sesterpenes.- 4.9 Carotenoids and vitamin A.- References.- 5 The shikimic acid pathway.- 5.1 Introduction.- 5.2 Quinones.- 5.3 Coumarins.- 5.4 Flavonoids.- References.- 6 Alkaloids.- 6.1 Introduction.- 6.2 Piperidine and pyrrolidine alkaloids.- 6.2.1 Piperidine alkaloids.- 6.2.2 Pyrrolidine alkaloids.- 6.3 Isoquinoline and related alkaloids.- 6.3.1 Phenethylamines and simple isoquinolines.- 6.3.2 Aporphines.- 6.3.3 Erythrina alkaloids.- 6.3.4 Morphine and related alkaloids.- 6.3.5 Hasubanonine and protostephanine.- 6.3.6 Protoberberine and related alkaloids.- 6.3.7 Phenethylisoquinoline alkaloids.- 6.4 Amaryllidaceae and mesembrine alkaloids.- 6.4.1 Amaryllidaceae alkaloids.- 6.4.2 Mesembrine alkaloids.- 6.5 Quinoline and related alkaloids.- 6.6 Indole alkaloids.- 6.6.1 Simple indole derivatives.- 6.6.2 Terpenoid indole and related alkaloids.- 6.7 Ipecac alkaloids.- 6.8 Miscellaneous alkaloids.- References.- 7 Microbial metabolites containing nitrogen.- 7.1 Introduction.- 7.2 Piperidine and pyridine metabolites.- 7.3 Diketopiperazines.- 7.4 Benzodiazepines.- 7.5 Metabolites derived from the tryptophan pathway.- 7.5.1 Ergot alkaloids.- 7.5.2 Cyclopiazonic acids and carbazomycin B.- 7.5.3 Indolmycin.- 7.5.4 Streptonigrin and pyrrolnitrin.- 7.6 Metabolites derived from the shikimate pathway.- 7.6.1 Pseudans, phenoxazinones, phenazines, and chloramphenicol.- 7.6.2 Ansamycins, mitomycins and antibiotic A23187.- 7.6.3 Cytochalasins and pseurotin A.- 7.6.4 Nybomycin.- 7.6.5 Naphthyridinomycin, saframycin A and CC-1065.- 7.6.6 Isocyanides and tuberin.- 7.6.7 Sarubicin A.- 7.6.8 Arphamenines.- 7.7 ?-Lactams.- 7.7.1 Penicillins and cephalosporins.- 7.7.2 Clavulanic acid.- 7.7.3 Nocardicins.- 7.7.4 Thienamycin and tabtoxin.- 7.8 Miscellaneous metabolites.- 7.8.1 Prodiginines.- 7.8.2 Elaiomycin and valinimycin.- 7.8.3 Streptothricin, acivicin, reductiomycin and asukamycin.- 7.8.4 Myxopyronin A, myxothiazol, angiolam A, rhizoxin and malonimycin.- 7.8.5 Virginiamycin antibiotics.- 7.8.6 Cyclizidine.- References.