Structure revision of the antibiotic pulvomycin

The hitherto accepted structure of the antibiotic pulvomycin (also known as labilomycin) has been shown to be incorrect. Fast atom bombardment mass spectrometry has shown pulvamycin to have a molecular weight of 838, and high field NMR experiments have allowed the structure to be deduced. Pulvomycin...

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Veröffentlicht in:Journal of the American Chemical Society 1985-05, Vol.107 (10), p.2849-2857
Hauptverfasser: Smith, Richard J, Williams, Dudley H, Barna, Jennifer C. J, McDermott, Ian R, Haegele, Klaus, Piriou, Francois, Wagner, Joseph, Higgins, William
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Sprache:eng
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Zusammenfassung:The hitherto accepted structure of the antibiotic pulvomycin (also known as labilomycin) has been shown to be incorrect. Fast atom bombardment mass spectrometry has shown pulvamycin to have a molecular weight of 838, and high field NMR experiments have allowed the structure to be deduced. Pulvomycin, which inhibits prokaryotic protein biosynthesis by binding to prokaryotic elongation factor Tu, has been shown by this tudy to possess a triene system, two trienone systems, and an unusual 22-membered lactone ring. It also contains one sugar unit, labilose, the previously deduced stereochemistry of which has been confirmed.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00296a004