Overview

This volume is part of a series, inaugurated in 1938, now referred to simply as ""Zechmeister"" after its founder, L. Zechmeister. It contains 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 reconized authority in his field, and provides a comprehensive and up-to-date review of the topic in question. This title looks at the chemistry of organic natural products. It is 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.

Full Product Details

Author:   W. Herz ,  H. Inouye ,  Lothar Jaenicke ,  M. Lounasmaa
Publisher:   Springer Verlag GmbH
Imprint:   Springer Verlag GmbH
Volume:   v.50
Weight:   0.590kg
ISBN:  

9783211819692

ISBN 10:   321181969
Pages:   270
Publication Date:   December 1986
Audience:   College/higher education ,  Professional and scholarly ,  Postgraduate, Research & Scholarly ,  Professional & Vocational
Format:   Hardback
Publisher's Status:   Active
Availability:   Out of stock  
The supplier is temporarily out of stock of this item. It will be ordered for you on backorder and shipped when it becomes available.
Language:   English & German

Table of Contents

The Irones and Their Precursors.- I. Introduction.- II. Isolation and Structure Determination.- III. Structure of the Irone Precursors.- IV. Stereochemistry of the Iridals and the Irones Derived from Them.- V. Minor Triterpenoids in Iris Extracts.- VI. Biogenesis of the Iridals.- VII. Mechanism of Irone Ring Formation.- VIII. Biological Significance of the Compounds.- References.- The Condylocarpine Group of Indole Alkaloids.- 1. Introduction.- 2. Structures.- 2.1. Precondylocarpine.- 2.2. Condylocarpines.- 2.3. Dihydrocondylocarpines.- 2.4. Tubotaiwinal.- 2.5. Aspidospermatidines.- 2.6. 19,20-Dihydroaspidospermatine.- 2.7. Geissovelline.- 2.8. Dichotines.- 3. Isolation and Occurrence.- 3.1. Isolation.- 3.2. Occurrence.- 4. Biogenesis.- 5. Chemistry.- 5.1. Correlation of Alkaloid Structures.- 5.1.1. Precondylocarpine and Condylocarpine.- 5.1.2. Tubotaiwine.- 5.1.3. N-oxides.- 5.1.4. Aspidospermatidines.- 5.1.5. Geissovelline and Dichotine.- 5.1.6. Further Alkaloids from Precondylocarpine.- 5.2. Total Syntheses.- 5.2.1. Condyfoline.- 5.2.2. Tubotaiwine.- 5.2.3. Condylocarpine.- 6. Physical Properties.- 6.1. X-ray Crystallography.- 6.2. 13C NMR Spectroscopy.- 6.3. 1H NMR Spectroscopy.- 6.4. Mass Spectrometry.- 6.5. Other Spectra.- 7. Pharmacology.- References.- The Antibiotics of the Pluramycin Group (4H-Anthra[1,2-b]pyran Antibiotics).- 1. Introduction.- 2. General Structural Characteristics and Nomenclature.- 3. The Families of Pluramycin Antibiotics.- 3.1. Pluramycin A and Neopluramycin.- 3.2. Kidamycin and Isokidamycin.- 3.3. Hedamycin.- 3.4. The Rubiflavins and Rubiflavinones.- 3.5. Largomycin FII Chromophore Constituents.- 3.6. PD 121,222.- 3.7. Chromoxymycin.- 3.8. The Griseorubins.- 3.9. The Indomycins and Indomycinones.- 4. Chemical Properties.- 4.1. Separation Techniques.- 4.1.1. Preparative Separations.- 4.1.2. Analytical Separations.- 4.2. Spectroscopy.- 4.2.1. UV/VIS Spectra.- 4.2.2. IR Spectra.- 4.2.3. 1H-NMR Spectra.- 4.2.4. 13C-NMR Spectra.- 4.2.5. Mass Spectra.- 4.3. Chemical Reactivity.- 4.3.1. General Chemical Characterization.- 4.3.2. Degradation, Decomposition.- 4.3.3. Derivatization.- 4.4. Stereochemistry.- 4.4.1. Configuration.- 4.4.2. Conformations.- 5. Total Synthesis.- 5.1. Pluramycinones.- 5.2. Sugar Moieties.- 5.3. Pluramycin Antibiotics.- 6. Biosynthesis.- 7. Biological and Biochemical Behaviour.- 7.1. General Remarks.- 7.2. Toxicity.- 7.3. Activity Against Bacteria, Yeasts and Other Microorganisms.- 7.4. Interaction with Phages and Lysogenic Bacteria.- 7.5. Cytotoxicity.- 7.6. Interaction with Nucleic Acids and Mode of Action.- Acknowledgement.- Note added in proof.- References.- Cyclosporine and Analogues - Isolation and Synthesis - Mechanism of Action and Structural Requirements for Pharmacological Activity.- 1. Introduction.- 1.1. History and Summary.- 1.2. Nomenclature.- 1.3. Production of Cyclosporine.- 1.4. Elucidation of the Structure of Cyclosporine - Conformation of Cyclosporine in the Crystal.- 1.5. Some Chemical Modifications of Cyclosporine.- 1.6. Natural Cyclosporine Analogues.- 1.7. Pharmacokinetics and Metabolism of Cyclosporine (1).- 1.8. Elucidation of the Conformation of Cyclosporine (1) in Aprotic Solvents.- 1.8.1. Backbone Conformation.- 1.8.2. Carbon Chains Conformations of Amino Acid Residues of Cyclosporine (1).- 1.8.3. Cyclosporine Conformation in Biological Fluids.- 2. Monoclonal Antibodies to Cyclosporine (1).- 2.1. The Antibody Response Induced by Cyclosporine.- 2.2. Fine Specificity of Monoclonal Antibodies.- 2.3. The Conformation of Cyclosporine Seen by Antibodies in Biological Fluids Seems to Be Similar to that Observed in Crystal.- 3. The Biosynthesis of Cyclosporine.- 4. Synthesis of Cyclosporine.- 4.1. Introduction.- 4.2. Synthesis of the Enantiomerically Pure Amino Acid MeBmt (83).- 4.2.1. Synthesis of (2R,3R)-3-methyl-1,2,4-butanetriol (65).- 4.2.2. Synthesis of (2R,3R,5E)-3-methyl-5-heptene-1,2-diol (71).- 4.2.3. Synthesis of (2R,3R,5E)-2-hydroxy-3-methyl-5-heptenal (76).- 4.2.4. Synthesis of (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoic acid (MeBmt) (83).- 4.3. Strategy Used for the Synthesis of Cyclosporine (1).- 4.4. Cyclosporine Analogues.- 4.4.1. Synthetic Analogues.- 4.4.2. Semi-synthetic Analogues.- 4.4.3. Conformation of Cyclosporine Analogues.- 5. Biological Activity and Structure-activity Relationships of Cyclosporine Analogues.- 5.1. Conclusions.- 6. Mechanism of Action of Cyclosporin A.- 6.1. Introduction.- 6.2. Lymphokines and the Immune System.- 6.3. Importance of Interleukin-2 for Lymphocytes.- 6.4. Cyclosporine and Transcriptional Control.- 6.5. Membrane and Cellular Receptors.- 6.6. Conclusions.- References.- Biosynthesis of Iridoids and Secoiridoids.- I. Introduction.- II. Classification of Iridoids and Secoiridoids.- III. Mevalonoid Origin of Iridoids and Secoiridoids and Mechanism of Formation of Iridane Skeleton from Acyclic Monoterpenes.- 1. Mevalonoid Origin of Iridoids and Secoiridoids.- 2. Mechanism of Formation of Iridane Skeleton from Acyclic Monoterpenes.- IV. Biosynthetic Processes After Cyclopentane Ring Formation.- 1. Intermediacy of Deoxyloganic Acid, 8-Epideoxyloganic Acid and Loganic Acid in Biosynthesis of Iridoids.- 2. Approach to Elucidation of the Mechanism of Cyclopentane Ring Cleavage of Loganin to Secologanin.- V. Biosynthetic Relationships Between Groups of Secoiridoid Glycosides.- 1. Sweroside-Morroniside Type Glycosides.- 2. Oeloside-10-Hydroxyoleoside Type Glycosides.- VI. Biosynthetic Pathways of Alkaloidal Glycosides and Hydrangenosides.- 1. Biosynthesis of Alkaloidal Glycosides and the Role of Strictosidine and Deacetylisoipecoside in the Biosynthesis of Alkaloids.- 2. Biogenesis of Hydrangenosides.- VII. Epilogue.- List of Compounds.- References.- Author Index.

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