6833. Oligomycins
Description and references
Macrolide antibiotic complex produced by an actinomycete similar to Streptomyces diastatochromogenes: Smith et al., Antibiot. Chemother. 4, 962 (1954); McCoy, Peterson, US 2927057 (1960 to Wisconsin Alumni Res. Foundation). Complex of several closely related compounds: Masamune et al., J. Am. Chem. Soc. 80, 6092 (1958). Separation of oligomycins A, B and C: Marty, McCoy, Antibiot. Chemother. 9, 286 (1959). Isoln and activity of D from Streptomyces rutgersensis: R. Q. Thompson et al., Antimicrob. Agents Chemother. 1961, 474. Partial structure of B: Prouty et al., Biochem. Biophys. Res. Commun. 44, 619 (1971); total structure of B: Glehn et al., FEBS Lett. 20, 267 (1972). Structures of A and C: G. T. Carter, Diss. Abstr. Int. B 37, 766 (1976); of D: C. Merienne, T. Staron, Chem. Commun. 1978, 318. Review: P. D. Shaw in Antibiotics vol. l, D. Gottlieb, P. D. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 585-610.
Derivative
Oligomycin A.Nomenclature
Properties
Two crystalline modifications, mp 140-141° and mp 150-151° (hexagonal crystals, melting with rapid decompn). uv max (abs ethanol): 225 nm (ε about 20,000). Solys at 25° (g/100 ml solvent): water 0.002; ether 28; benzene 6; Skellysolve B 0.02; abs ethanol 25; glacial acetic acid 37.5; acetone 85.Derivative
Oligomycin B.Nomenclature
Description and references
Potent inhibitor of oxidative phosphorylation: Lardy et al., Arch. Biochem. Biophys. 78, 587 (1958).
Derivative
Oligomycin C.Nomenclature
Derivative
Oligomycin D.Nomenclature
Properties
mp 116-119°. [α]D20 -62° (c = 1.36 in CHCl3).Therapeutic Category
Oligomycin D as antifungal.
Keywords
Antifungal (Antibiotics)