Title: Oligomycins
Literature 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 Type: Oligomycin A
CAS Registry Number: 579-13-5
Molecular Formula: C45H74O11
Molecular Weight: 791.06
Percent Composition: C 68.32%, H 9.43%, O 22.25%
Properties: Two crystalline modifications, mp 140-141° and mp 150-151° (hexagonal crystals, melting with rapid decompn). uv max (abs ethanol): 225 nm (e 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.
Melting point: mp 140-141° and mp 150-151° (hexagonal crystals, melting with rapid decompn)
Absorption maximum: uv max (abs ethanol): 225 nm (e about 20,000)
Derivative Type: Oligomycin B
CAS Registry Number: 11050-94-5
CAS Name: 28-Oxooligomycin A
Molecular Formula: C45H72O12
Molecular Weight: 805.05
Percent Composition: C 67.14%, H 9.01%, O 23.85%
Literature References: Potent inhibitor of oxidative phosphorylation: Lardy et al., Arch. Biochem. Biophys. 78, 587 (1958).
Derivative Type: Oligomycin C
CAS Registry Number: 11052-72-5
CAS Name: 12-Deoxyoligomycin A
Molecular Formula: C45H74O10
Molecular Weight: 775.06
Percent Composition: C 69.73%, H 9.62%, O 20.64%
Derivative Type: Oligomycin D
CAS Registry Number: 1404-59-7
CAS Name: 26-Demethyloligomycin A
Additional Names: rutamycin
Manufacturers' Codes: A-272; RR-32705
Molecular Formula: C44H72O11
Molecular Weight: 777.04
Percent Composition: C 68.01%, H 9.34%, O 22.65%
Properties: mp 116-119°. [a]D20 -62° (c = 1.36 in CHCl3).
Melting point: mp 116-119°
Optical Rotation: [a]D20 -62° (c = 1.36 in CHCl3)
Therap-Cat: Oligomycin D as antifungal.
Keywords: Antifungal (Antibiotics). |