DEOXY DERIVATIVES OF BUTIROSIN A AND 5"-AMINO-5"-DEOXYBUTIROSIN A, AMINOGLYCOSIDE ANTIBIOTICS RESISTANT TO BACTERIAL 3'-PHOSPHORYLATIVE ENZYMATIC INACTIVATION SYNTHESIS AND NMR STUDIES

3'-Deoxybutirosin A (4), 5"-amino-3', 5"-dideoxybutirosin A (6), and 5"-amino-4', 5"-dideoxybutirosin A (7) were prepared by deoxygenation of the appropriate hydroxyl in suitably protected derivatives of butirosin A, using sequentially trifluoromethylsulfonylation,...

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Bibliographic Details
Published in:Journal of antibiotics 1982, Vol.35(6), pp.692-702
Main Author: WOO, PETER W. K.
Format: Article
Language:English
Subjects:
Aminoglycosides - chemical synthesis
Animals
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - metabolism
Anti-Bacterial Agents - pharmacology
Butirosin Sulfate - chemical synthesis
Butirosin Sulfate - pharmacology
Drug Resistance, Microbial
Magnetic Resonance Spectroscopy
Male
Mice
Phosphorylation
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Summary:3'-Deoxybutirosin A (4), 5"-amino-3', 5"-dideoxybutirosin A (6), and 5"-amino-4', 5"-dideoxybutirosin A (7) were prepared by deoxygenation of the appropriate hydroxyl in suitably protected derivatives of butirosin A, using sequentially trifluoromethylsulfonylation, displacement with benzenethiolate, and hydrogenolysis. The structures of the compounds were confirmed by NMR spectroscopy, using 13C NMR and 1H NMR at up to 600 MHz. The compounds are broad-spectrum antibiotics active against resistant microorganisms which i n activate butirosin and related aminoglycosides by 3'-phosphorylation.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.35.692