Polyether Antibiotics Naturally Occurring Acid Ionophores, Volume 2: Chemistry

Description

This collection of essays will stimulate the use of ionophores in different research areas. It includes information on potential breakthroughs in the halogenated derivatives of lasalocid and ethers of antibiotic A204A, polyethers and analytical techniques used to unravel their complex structures. Cover Half Title Title Page Copyright Page Table of Contents Foreword Preface List of Contributors Contents of Volume 1—Biology 1. Chemical Synthesis I. Introduction II. Synthetic Methods A. β-Hydroxy Ketone B. Spiroketal C. Tetrahydrofurans D. Tetrahydropyrans E. 1,2-Stereochemistry F. Chiral Starting Materials III. Total Syntheses A. A23187 (Calcimycin) B. Evans Synthesis C. Grieco Synthesis D. Ogawa Synthesis E. Lasalocid A (X-537A) F. Kishi Synthesis G. Ireland Synthesis H. Monesin I. Kishi Synthesis J. Still Synthesis References Bibliography 2. Chemical Transformations of Polyether Antibiotics I. Introduction II. Lasalocid A. Chemical Modifications B. Biological Activity III. Monensin and Dianemycin IV. Nigericin and X-206 V. Antiobiotic A204 A. Chemical Modifications B. Biological Activity VI. Grisorixin and Alborixin VII. Lysocellin A. Chemical Modifications B. Biological Activity VIII. Lonomycin A. Chemical Modifications B. Biological Activity IX. Salinomycin X. Conclusions References 3. X-Ray Structures of the Polyether Antibiotics I. Introduction II. Polyether Antibiotics III. Conclusion References 4. Mass Spectrometry of Polyether Antibiotics I. Introduction II. General Considerations III. Alborixin Group IV. Dianemycin Group V. Lasalocid Group VI. Lysocellin Group VII. Miscellaneous Group VIII. Monensin Group IX. Nigericin Group X. Noboritomycin Group XI. Salinoraycin Group XII. Summary References 5. Structure, Conformation, and Mechanism of Action as Revealed by Proton NMR I. Introduction Scope and Limitations of [sup(1)]H NMR Spectroscopy II. Stereo Notation and Coding A. Symbols B. Structural Representations of Some Carboxylic Acid Lonophores C. Stereoviews D. Spectral Representations III. Applied Methodology and Criteria A. General Considerations B. Operational Strategies C. [sup(1)]H Chemical Shifts and Their Predictability D. Coupling Constants and Conformation E. Hydroxy Groups F. ASIS Effects and Lipophilicity Index IV. Primary Structure and Predestination to Conformational Bias A. General Considerations: Definition of Hinges B. Conformational Rules C. Practical Applications of Conformational Rules: Static and Dynamic Features V. Conclusion References 6. [sup(13)]C NMR Spectra of Polyether Antibiotics I. Introduction II. Techniques Used for [sup(13)]C Assignments of Polyether Antibiotics A. Differentiation of Methyl, Methylene, Methine, and Quaternary Carbon Signals B. Selective Proton Decoupling C. Biosynthetic Labeling Method III. Classification of Polyether Antibiotics IV. [sup(13)]C NMR Spectra of Polyether Antibiotics A. Group 1 B. Group 2 C. Group 3 D. Group 4 E. Group 5 V. [sup(13)]C Chemical Shift Trends of Polyether Antibiotics A. Some Empirical Rules for the Structural Elucidation of Polyether Antibiotics by [sup(13)]C NMR Spectroscopy B. Application of the "Empirical Rules" for the Structural Elucidation of Antibiotic 6016 VI. Conclusion References Author Index Subject Index