The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
CHEMISTRY OF MADURAMICIN
II. DECARBOXYLATION, ABNORMAL KETALIZATION AND DEHYDRATION
W. J. MCGAHRENG. O. MORTONM. M. SIEGELD. B. BORDERSJ. C. JAMESG. A. ELLESTAD
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1986 Volume 39 Issue 11 Pages 1541-1550

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Abstract

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.

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© Japan Antibiotics Research Association
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