Dactylocyclines, novel tetracycline derivatives produced by a Dactylosporangium sp. II. Structure elucidation.
Fermentation of Dactylosporangium sp. (ATCC 53693) produces a mixture of tetracycline derivatives from which several related tetracycline glycosides, the dactylocyclines, were isolated and their structures determined. The most abundant glycoside in initial fermentations was found to be dactylocycline A. Each glycoside proved to be acid sensitive and readily hydrolyzed to a common aglycone, dactylocyclinone. While the aglycone was cross resistant with tetracycline, the dactylocyclines proved active against certain tetracycline-resistant organisms.
Tymiak
A A
AA
Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, NJ 08543-4000.
Ax
H A
HA
Bolgar
M S
MS
Kahle
A D
AD
Porubcan
M A
MA
Andersen
N H
NH
D000192:Actinomycetales / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002751:Chlortetracycline / Q000031:analogs & derivatives* / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D000095702:Polyether Toxins
D000900:Anti-Bacterial Agents; D002751:Chlortetracycline; C054353:dactylocyclinone; C079468:dactylocycline D; D000095702:Polyether Toxins; C079469:dactylocycline E