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:   Bertram O. Fraser-Reid ,  H. Jones ,  T. Kasai ,  P. O. Larsen
Publisher:   Springer Verlag GmbH
Imprint:   Springer Verlag GmbH
Volume:   39
Weight:   0.820kg
ISBN:  

9783211815304

ISBN 10:   3211815309
Pages:   330
Publication Date:   April 1980
Audience:   College/higher education ,  Professional and scholarly ,  Postgraduate, Research & Scholarly ,  Professional & Vocational
Format:   Hardback
Publisher's Status:   Active
Availability:   Out of stock  
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Table of Contents

Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products.- I. Introduction.- II. Some Background Information.- III. Some Attributes of Carbohydrate Synthons.- 1. Enantiomeric Purity.- 2. Conformational Bias.- 3. Ready Proof of Structure.- 4. Latent Functionalities.- IV. Syntheses.- 1. Acyclic Transfer.- a) L-erythro-Biopterin.- b) Pyridomycin.- c) (+)- and (-)-Frontalin.- d) (+)- and (-)-exo-Brevicomin.- e) Erythronolide.- 2. Cyclic Transfer of Pyranoids.- a) Thromboxane.- b) Asperlin.- c) ?-Multistriatin.- 3. Cyclic Transfer of Furanoids.- a) (-)-Avenaciolide.- b) (+)-Avenaciolide.- c) (-)-Isoavenaciolide.- d) (-)-Canadensolide.- e) 11-Oxaprostaglandin.- f) d-Oxybiotin.- g) (+)-Biotin.- 4. Transcription.- a) Prostaglandins.- b) An Approach to Tetrodotoxin.- c) Chiral Cycloalkanes from Annulated Pyranosides.- d) Cyclopropano Pyranosides.- e) Cyclobutano Pyranosides.- f) Cyclohexano Pyranosides.- g) Cyclopentano Furanosides.- References.- Recent Advances in the Biology and Chemistry of Vitamin D.- I. Biology and Biochemistry of Vitamin D.- 1. Introduction.- 2. 25-Hydroxyvitamin D3 and l?,25-Dihydroxyvitamin D3.- 3. Calcium.- 4. 24(R) 25-Dihydroxyvitamin D3.- 5. 25,26-Dihydroxyvitamin D3.- 6. Clinical Aspects.- II. Partial and Total Synthesis.- 1. Introduction.- 2. Side Chain Modification.- a) 25-Hydroxycholesterols.- b) 24,25-Dihydroxycholesterol and 25,26-Dihydroxycholesterol.- c) Side Chain Analogs of Vitamin D.- 3. Ring Modified Sterols.- a) l?-Hydroxycholesterols.- b) Other A-Ring Modifications.- c) Reactions in the B-Ring of Sterols.- 4. Analogs Prepared by Modification of Vitamin D and Related Compounds.- 5. Total Synthesis.- a) A-Ring Precursors.- b) C-D Ring and Side Chain Fragments.- c) Other Approaches.- III. Photolytic and Thermal Conversions of the Vitamin D Isomers.- 1. Photolysis of the Provitamin.- 2. Photolysis of the Previtamin.- 3. Photolysis of Vitamin D.- 4. Thermolysis of Previtamin D.- References.- Stereochemistry of Naturally Occurring Carotenoids.- I. General Introduction.- II. Historical.- III. Methods and Application.- 1. X-Ray Crystallography.- 2. Electronic Spectra.- 3. Vibrational Spectra.- 4. Proton Nuclear Magnetic Resonance Spectroscopy.- 5. 13C Nuclear Magnetic Resonance Spectroscopy.- a) Authentic Carotenoids.- b) Use in Structural Elucidation.- 6. Optical Rotatory Dispersion and Circular Dichroism.- 7. Linear Dichroism.- 8. High Pressure Liquid Chromatography.- 9. Horeau Method.- 10. Oxidative Degradation.- 11. Partial Synthesis.- 12. Total Synthesis.- a) Racemic Carotenoids.- b) Optically Active Model Carotenoids.- c) Optically Active Carotenoids.- d) Z-Isomers.- IV. Geometrical Isomerism.- V. Established Chirality.- VI. Chirality and Biogenetic Relationships.- 1. De novo Synthesis.- 2. Metabolic Transformations.- 3. Carotenoproteins.- References.- Chemistry and Biochemistry of ?-Glutamyl Derivatives from Plants Including Mushrooms (Basidiomycetes).- I. Introduction.- II. Nomenclature.- III. Structures and Distribution of ?-Glutamyl Derivatives from Plants.- 1. ?-Glutamyl Derivatives of Protein Amino Acids.- 2. ?-Glutamyl Derivatives of Non-Protein Amino Acids Which Do not Contain Sulphur or Selenium.- 3. ?-Glutamyl Derivatives of Non-Protein Amino Acids Containing Sulphur or Selenium.- 4. ?-Glutamyl Derivatives of Amines.- 5. Distribution Patterns for the ?-Glutamyl Derivatives.- VI. Chemical, Spectroscopic, and Analytical Properties of ?-Glutamyl Derivatives.- 1. pK-Values.- 2. Optical Activity.- 3. Infrared Spectra.- 4. NMR-Spectra.- 5. Gas Chromatography, Mass Spectroscopy, and Combined Gas Chromatography-Mass Spectroscopy.- 6. Paper Chromatography.- 7. Paper Electrophoresis.- 8. Ion-Exchange Chromatography.- 9. Degradation and General Chemical Properties of ?-Glutamyl Derivatives.- 10. Isolation Procedures and Stability of ?-Glutamyl Derivatives.- 11. Establishment of the ?-Linkage.- V. Isolation and Structure Determination of Individual Compounds.- 1. ?-L-Glutamyl-?-cyano-l-alanine.- 2. Linatine (l-[(N-?-l-Glutamyl)amino]-D-proline).- 3. ?-Glutamylvalylglutamic Acid.- 4. ?-L-Glutamyl-l-phenylalanyl-l-willardiine.- 5. ?-L-Glutamyl-?-l-glutamyl-l-phenylalanine.- 6. ?-Glutamylmarasmine (?-l-Glutamyl-3-(methylthiomethylsulphinyl)-l-alanine).- 7. Lentinic Acid (2- ?-l-Glutamylamino-4,6,8,10,10-pentaoxo-4,6,8,10-tetrathiaundecanoic Acid).- 8. N,N-bis-(?-Glutamyl)-3,3?-(1-methylethylene-1,2-dithio)-dialanine.- 9. ?-l-Glutamyl-L-cysteinyl-?-alanine.- 10. ?-l-Glutamyl-S-(prop-1-enyl)-cysteinyl-S-(prop-1-enyl)-l-cysteine sulphoxide.- 11. ?-l-Glutamyl-S-(2-carboxypropyl)-l-cysteinylglycinfe.- 12. ?-Glutamyl-?-glutamylmethionine.- 13. N5-(1-Methyl-2-oxopentyl)-l-glutamine.- 14. N5-(2-Cyanoethyl)-l-glutamine.- 15. Coprine (N5-(l-Hydroxycyclopropyl)-l-glutamine).- 16. N5-(3,4-Dioxocyclohexa-l,5-dien-l-yl)-l-glutamine.- 17. Agaritine (N5-[(4-Hydroxymethylphenyl)amino]-l-glutamine).- VI. Synthesis.- 1. General Discussion.- 2. Linatine (l-[(N- ?-l-Glutamyl)amino]-d-proline).- 3. Hypoglycine B (?-L-Glutamyl-(2S,1?R)-3-methylene-cyclopropyl)-alanine.- 4. Coprine (N5-(l-hydroxycyclopropyl)-l-glutamine).- 5. Agaridoxin (N5-(3,4-Dihydroxyphenyl)-l-glutamine).- 6. Agaritine (N5-[(4-Hydroxymethylphenyl)amino]-l-glutamine).- VII. Biosynthesis and Transformations of ?-Glutamyl Derivatives in Plants.- 1. Glutathione in Plants and Its Relationship to Other Plant ?-Glutamyl Derivatives.- 1.1. Occurrence and Isolation of Glutathione.- 1.2. Biosynthesis of ?-Glutamylcysteine and Glutathione.- 1.3. The Function of Glutathione in Plants.- 1.4. Degradation of Glutathione in Plants.- 2. Biosynthesis of Glutamine in Plants.- 3. ?-Glutamyl Transferases in Plants.- 4. Degradation Systems for ?-Glutamyl Derivatives in Plants.- 5. Occurrence of ?-Glutamyl Derivatives in Different Parts of Plants and During the Life Cycles of Plants.- 6. Specific Systems for Biosynthesis and Degradation of Individual ?-Glutamyl Derivatives.- 6.1. ?-l-Glutamyl-?-cyano-l-alanine.- 6.2. ?-Glutamyl Derivatives of Sulphur-Containing Amino Acids in Allium Species.- 6.3. Lentinic Acid and ?-Glutamylmarasmine.- 6.4. Theanine (N5-Ethyl-l-glutamine) and N5-Methyl-l-glutamine.- 6.5. N5-(4-Hydroxyphenyl)-l-glutamine, Agaridoxin (N5-(3,4-Dihydroxyphenyl)-l-glutamine), and N5-(3,4-Dioxocyclohexa-l,5-dien-l-yl)-l-glutamine.- 7. The ?-Glutamyl Cycle and ?-Glutamyl Derivatives in Plants.- 7.1. The Cycle in Animals and Microorganisms.- 7.2. Evidence for the Presence in Plants of the Enzymes Involved in the ?-Glutamyl Cycle.- 7.3. Transport of Amino Acids Across Cell Membranes in Plants.- 8. Conclusions.- VIII. ?-Glutamyl Derivatives with Toxic or Other Specific Biological Properties.- 1. ?-l-Glutamyl-?-cyano-l-alanine and N5-(2-Cyanoethyl)-l-glutamine.- 2. Linatine (l-[(N- ?-l-Glutamyl)amino]-d-proline).- 3. HypoglycineB(?-L-Glutamyl-(2S,1?R)-3-(methylenecyclopropyl)-alanine).- 4. ?-l-Glutamyl-Se-methylseleno-l-cysteine.- 5. Coprine (N5-(l-Hydroxycyclopropyl)-l-glutamine).- 6. N5-(3,4-Dioxocyclohexa-l,5-dien-l-yl)-l-glutamine.- IX. Compounds Structurally Related to ?-Glutamyl Derivatives from Plants.- X. Summary.- Acknowledgements.- Addendum.- References.- Author Index.

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