Fortschritte Der Chemie Organischer Naturstoffe Progress in the Chemistry of Organic Natural Products 69

ISBN-13: 9783709173541 / Angielski / Miękka / 2012 / 273 str.

D. Deepak; J. F. Grove; E. Haslam

Opis

The volumes of this classic series, now referred to simply as "Zechmeister after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline."

Spis treści

Non-Macrocyclic Trichothecenes, Part 2.- 1. Introduction and Nomenclature.- 2. Naturally Occurring Compounds.- 3. Unnatural Trichothecenes.- 4. Chemistry.- 4.1. Ethylenic Double Bonds.- 4.1.1. Isomerization.- 4.1.2. Catalytic Reduction.- 4.1.3. Electrophilic Addition Reactions.- 4.1.3.1. Epoxidation of 9-Enes.- 4.1.3.2. Epoxidation of 12-Enes.- 4.1.3.3. Epoxidation of 7-Enes.- 4.1.3.4. Hydroxylation.- 4.1.3.5. Bromination.- 4.1.3.6. Carbene Addition.- 4.1.4. Reactions at the ?-Carbon Atom.- 4.1.5. Ozonolysis.- 4.2. Hydroxyl Groups.- 4.2.1. Regioselective Esterification and Etherification, and Regeneration of the Hydroxyl Function.- 4.2.1.1. Verrucarol.- 4.2.1.2. Scirpenetriol.- 4.2.1.3. T-2 Tetraol.- 4.2.1.4. Vomitoxin and Nivalenol.- 4.2.1.5. 12-Ols.- 4.2.2. Regioselective Oxidation.- 4.2.2.1. 8-Ols.- 4.2.2.2. 15-Ols.- 4.2.2.3. 3-Ols.- 4.2.2.4. 4-Ols.- 4.2.2.5. 12-Ols.- 4.2.3. Deoxygenation.- 4.2.4. Nucleophilic Substitution.- 4.3. Keto Groups.- 4.3.1. Derivative Formation.- 4.3.2. Regio- and Stereo-Selective Reduction.- 4.3.3. Nucleophilic Addition Reactions.- 4.3.3.1. Phosphorus Ylides.- 4.3.3.2. Sulphur Ylides.- 4.3.4. Enolization, and Reactions at the ?-Carbon Atom.- 4.3.5. Isomerization.- 4.4. Epoxide Function.- 4.4.1. 12,13-Epoxide.- 4.4.1.1. The Trichothecene ? 10,13-Cyclotrichothecane Rearrangement.- 4.4.1.2. The Trichothecene ? Apotrichothecene Rearrangement.- 4.4.1.3. Deoxygenation.- 4.4.2. 7,8-Epoxide.- 4.4.3. 9,10-Epoxide.- 5. Biosynthesis.- 5.1. Mevalonate to Trichodiene.- 5.2. Trichodiene (and Its Relatives) to 12,13-Epoxytrichothecene and Isotrichodermin.- 5.3. Further Oxygenation and Esterification of the Trichothecene Nucleus.- 5.4. Inhibitors of Trichothecene Biosynthesis.- 6. Metabolism.- 6.1. Cleavage of Ester Groups.- 6.2. Hydroxylation.- 6.3. 12,13-Deoxygenation.- 6.4. Glucuronide Formation.- 7. Spectroscopy.- 7.1. Nuclear Magnetic Resonance Spectra.- 7.1.1. 1H-Spectra.- 7.1.2. 13C-Spectra.- 7.2. Mass Spectra.- References.- Cardiac Glycosides.- 1. Introduction.- 2. Isolation and Identification.- 2.1. Structural Features of Cardiac Genins.- 2.2. Sugars of Cardiac Glycosides.- 2.3. Sequence, Number and Identification of Monosaccharides.- 2.4. I.R. Spectroscopy of Cardiac Glycosides.- 2.5. Mass Spectrometry of Cardiac Glycosides.- 2.6. NMR Spectrometry of Cardiac Glycosides.- 3. Biological Activity.- Acknowledgements.- Table 1. Cardenolide Glycosides Isolated from Plants.- Table 2. Bufadienolide Glycosides Isolated from Plants.- Table 3. Formulas of Cardiac Glycosides.- References.- Aspects of the Enzymology of the Shikim Pathway.- 1. Introduction.- 2. The Shikimate Metabolic Pathway.- 2.1. Common Pathway — Enzymes and Intermediates.- 2.2. Common Pathway — Enzymology.- 2.2.1. 3-Deoxy-D-arabino-heptulosonate 7-phosphate (DAHP) Synthase.- 2.2.2. 3-Dehydroquinate Synthase.- 2.2.3. 3-Dehydroquinate Dehydratase (3-Dehydroquinase).- 2.2.4. Shikimate Dehydrogenase (Shikimate Oxido-Reductase).- 2.2.5. Shikimate Kinase.- 2.2.6. 5-Enolpyruvylshikimate-3-phosphate Synthase (5-EPSP Synthase).- 2.2.7. Chorismate Synthase.- 2.3. Pathways Beyond Chorismate — Enzymes and Intermediates.- 2.3.1. Pathways to L-Phenylalanine and L-Tyrosine.- 2.3.1.1. Chorismate Mutase — Monofunctional.- 2.3.1.2. Chorismate Mutase — Bifunctional.- 2.3.1.3. Monofunctional Prephenate Dehydratase and Prephenate Dehydrogenase.- 2.3.1.4. Aminotransferases.- 2.3.1.5. L-Arogenate ( “Pretyrosine”) Metabolism.- 2.3.2. Pathway to L-Tryptophan.- 2.3.2.1. Anthranilate Synthase.- 2.3.2.2. Anthranilate-5?-phosphoribose-l-pyrophosphate Phosphoribosyl Transferase, iV-(5?-Phosphoribosyl)-anthranilate Isomerase and Indole-3-glycerolphosphate Synthase.- 2.3.2.3. Tryptophan Synthase.- 2.3.3. Folate Coenzymes, Isoprenoid Quinones and Enterochelin.- 2.3.3.1. p-Aminobenzoate Synthase.- 2.3.3.2. Isochorismate Synthase and Enterochelin (Enterobactin).- 2.3.4. Phenylpropanoid Metabolism in Plants.- 2.3.4.1. L-Phenylalanine Ammonia Lyase (PAL).- 2.4. Metabolic “Costs” of Aromatic Amino Acid Biosynthesis.- 3. Enzyme Mechanisms.- 3.1. 3-Deoxy-D-arabino-heptulosonate-7-phosphate (DAHP) Synthase.- 3.2. 3-Dehydroquinate Synthase (7-Phospho-3-deoxy-D-arabimo-heptulosonate Phosphate Lyase).- 3.3. 5-Enolpyruvylshikimate-3-phosphate (5-EPS-3-P) Synthase.- 3.3.1. Glyphosate.- 3.4. Chorismate Synthase.- 3.5. Chorismate Mutase.- 4. Multifunctional Enzymes.- 5. Genetic Engineering.- 5.1. Biocatalytic Syntheses of Aromatics from D-Glucose.- 5.2. Anthocyanin Biosynthesis — Genetic Manipulation of Flower Colour.- Notes Added in Proof.- References.- Author Index.