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.
Author(s): John W. Westley
Publisher: CRC Press
Year: 2023
Language: English
Pages: 431
City: Boca Raton
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
