The Biosynthesis of Secondary Metabolites

ISBN-13: 9789400958357 / Angielski / Miękka / 2011 / 178 str.

R. B. Herbert; R. B. Herbert

Opis

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. Investiga- tion of secondary metabolism began with curiosity about the struc- tures 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. This account is primarily intended to be an introduction to the biosynthesis of secondary metabolites. I have also endeavoured, however, to make the book as comprehensive as possIble. This has meant that some of the material has had to be presented in abbrevi- ated form. The abbreviated material is largely confined to particular sections of the book. The paragraphs marked with a dagger (t) can be omitted by the reader wishing to acquire a general introduction to the subject. A blend of the most significant and the most recent references is cited to provide the reader with ready access to the primary litera- ture. This is clearly most necessary for the material presented in abbreviated form. Relevant reviews are also cited.

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.- 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.- 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.- 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.- 5 The shikimic acid pathway.- 5.1 Introduction.- 5.2 Quinones.- 5.3 Coumarins.- 5.4 Flavonoids.- 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 Phenylethylisoquinoline 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.- 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 acid.- 7.5.3 Indolmycin.- 7.5.4 Streptonigrin and pyrrolnitrin.- 7.5.5 Pseudans, phenoxazinones, phenazines, and chloramphenicol.- 7.6 Miscellaneous metabolites.- 7.6.1 Mitomycins and ansamycins.- 7.6.2 Cytochalasins.- 7.6.3 Nybomycin.- 7.6.4 Prodiginines.- 7.6.5 ?-Lactams.