CHEMICAL MODIFICATION OF SOME GENTAMICINS AND SISOMICIN AT THE 3"-POSITION

Chemical and photochemical oxidative methods of de-N-methylation of some gentamicins and sisomicins at the 3"-position are described. Selective acetylation of gentamicins and sisomicins at the 1, 3, 2' and 6' and of gentamicin B at the 1, 3, and 6' positions are achieved by treat...

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Bibliographic Details
Published inJournal of antibiotics Vol. 31; no. 1; pp. 43 - 54
Main Authors NAGABHUSHAN, T. L., WRIGHT, J. J., COOPER, A. B., TURNER, W. N., MILLER, G. H.
Format Journal Article
LanguageEnglish
Published Japan JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1978
Subjects
Acetylation
Alkylation
Bacteria - drug effects
Drug Resistance, Microbial
Gentamicins - analogs & derivatives
Gentamicins - pharmacology
Methods
Methylation
Sisomicin - analogs & derivatives
Sisomicin - pharmacology
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Summary:Chemical and photochemical oxidative methods of de-N-methylation of some gentamicins and sisomicins at the 3"-position are described. Selective acetylation of gentamicins and sisomicins at the 1, 3, 2' and 6' and of gentamicin B at the 1, 3, and 6' positions are achieved by treatment of the free bases with carbon dioxide prior to acetylation. De-N-methylation of the above selectively blocked gentamicins and sisomicins followed by re-alkylation at the 3"-position and de-N-protection gives a series of 3"-N-alkyl analogues. The in vitro antibacterialproperties of the new derivatives of gentamicins and sisomicins are given.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.31.43