Coloradocin, an antibiotic from a new Actinoplanes. II. Identity with luminamicin and elucidation of structure.
Coloradocin was isolated from a fermentation broth by adsorption onto Amberlite XAD-2. The activity was eluted in MeOH and purified by gel filtration on Shephadex LH-20, followed by liquid-liquid chromatography on diol-bonded silica gel. The last two steps in the purification of this antibiotic included reverse-phase chromatography on C18-bonded silica gel and countercurrent chromatography on an Ito Coil Planet Centrifuge to give material of 90% purity. Analytically pure material was obtained by preparative HPLC. As a result of extensive homo and heteronuclear two-dimensional NMR studies, a structure was proposed for coloradocin. The structure consists of a decalin ring system fused to a 10-membered macrolactone which in turn is fused to a 14-membered macrolactone possessing an enol ether in conjugation with an unsaturated cyclic anhydride functionality. Coloradocin is related to a small class of antibiotics which include nodusmicin and nargenicin and was shown to be identical to luminamicin for which no structure has been reported.
Rasmussen
R R
RR
Pharmaceutical Products Division, Abbott Laboratories, Abbott Park, Illinois 60064.
Scherr
M H
MH
Whittern
D N
DN
Buko
A M
AM
McAlpine
J B
JB
D000900:Anti-Bacterial Agents / Q000302:isolation & purification; D000903:Antibiotics, Antineoplastic / Q000145:classification* / Q000302:isolation & purification; D055598:Chemical Phenomena; D002621:Chemistry; D007783:Lactones; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation
D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D007783:Lactones; C047328:luminamicin