CHEMISTRY OF MADURAMICIN: II. DECARBOXYLATION, ABNORMAL KETALIZATION AND DEHYDRATION

The behavior of the free acid and ammonium salt of maduramicin towards heat and alcohols is examined. In refluxing lower alcohols the free acid material is decarboxylated. In addition a bisketal decarboxylated compound as well as an A-ring monoketal decarboxylated derivative are formed. Heating the...

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Bibliographic Details
Published in:Journal of antibiotics 1986, Vol.39(11), pp.1541-1550
Main Authors: MCGAHREN, W. J., MORTON, G. O., SIEGEL, M. M., BORDERS, D. B., JAMES, J. C., ELLESTAD, G. A.
Format: Article
Language:English
Subjects:
Chemical Phenomena
Chemistry
Coccidiostats
Decarboxylation
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lactones
Magnetic Resonance Spectroscopy
Organic chemistry
Preparations and properties
Pyrans
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Summary:The behavior of the free acid and ammonium salt of maduramicin towards heat and alcohols is examined. In refluxing lower alcohols the free acid material is decarboxylated. In addition a bisketal decarboxylated compound as well as an A-ring monoketal decarboxylated derivative are formed. Heating the ammonium salt of the ionophores in suspension in water, or dissolved in inert solvents such as heptane or xylene can cause decarboxylation as well as concomitant dehydration of the F-ring. Reaction of dansyl chloride with the free acid of maduramicin can cause dehydration of the B-ring under very mild conditions.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.39.1541