EPIMERIZATION OF ERYTHROMYCIN DERIVATIVES

Dirithromycin (3) isomerizes upon dissolution in different solvents. From X-ray analysis of V-T 108, an analogue of dirithromycin, and comparative 1H and 13C NMR, and MS data, the isomer of dirithromycin was confirmed to be the C-16-(S)-epimer. The ratio of the two epimers at equilibrium conditions...

Full description

Saved in:
Bibliographic Details
Published inJournal of antibiotics Vol. 43; no. 10; pp. 1271 - 1277
Main Authors FIRL, JOACHIM, PROX, AXEL, LUGER, PETER, MAIER, ROLAND, WOITUN, EBERHARD, DANECK, KLAUS
Format Journal Article
LanguageEnglish
Published Tokyo JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1990
Japan Antibiotics Research Association
Subjects
Anti-Bacterial Agents
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Chromatography, Thin Layer
Crystallization
Erythromycin - analogs & derivatives
Erythromycin - chemistry
Macrolides
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medical sciences
Molecular Conformation
Pharmacology. Drug treatments
Stereoisomerism
Antibiotic
Chemical modification
Epimerization
Structure activity relation
Molecular structure
Macrolide
Online AccessGet full text

Cover

More Information
Summary:Dirithromycin (3) isomerizes upon dissolution in different solvents. From X-ray analysis of V-T 108, an analogue of dirithromycin, and comparative 1H and 13C NMR, and MS data, the isomer of dirithromycin was confirmed to be the C-16-(S)-epimer. The ratio of the two epimers at equilibrium conditions was approximately 8:2 (R/S) in methanol at room temperature.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.43.1271