Characterization of the oligomycins and related antibiotics

Chamberlin, James W.; Gorman, Marvin; A, Agtarap

doi:10.1016/0006-291x(69)90402-1

Cited by 22 publications

(3 citation statements)

References 4 publications

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“…The methylated fraction was chromatographed by preparative TLC developed with benzene/EtOAc (5/3). The zone between R¡ 0.06-0.12 contained 8: TLC R¡ 0.37 in 5% MeOH in CHC13; IR (CHC13) Vma 3510; 2968, 2921, 2873,1727,1715,1455, 1380,1353,1170,1012, 998 cm"1; EIMS, m/z (relative intensity) 297 (M -H20 -CH3CO, 62), 217 (26), 211 (100), 199 (29), 187 (56), 155 (19), 137 (81), 125 (19), 124 (28), 115 (20); NMR 4.54 (1 H, d, 2.9 Hz), 3.70 (3 H, s), 3.47 (2 H, bs), 2.92 (1 H, dd, 15.4, 2.9 Hz), 2.46 (1 H, dd, 15.4, 5.1 Hz), 2.31 (3 H, s), 1.13 (3 H, d, 6.4 Hz), 1.05 (3 H, d, 6.6 Hz), 1.01 (3 H, d, 6.10 Hz), 0.851 (3 H, d, 6.8 Hz); NaBH4 Reduction of 12. Compound 13.…”

Section: Methodsmentioning

confidence: 99%

“…The extract was washed with 5% NaHCOg and dried over MgS04 and subjected to preparative TLC with 10% MeOH/CHClg. The zone R¡ 0.35-0.47 yielded 17, Rf 0.275 in 7% MeOH/CHCl3: EIMS, m/z (relative intensity) 398 (M+, 3), 380 (6), 310 (24), 268 (11), 253 (24), 235 (9), 213 (20), 185 (22), 184 (100), 179 (20), 173 (58), 155 (53), 138 (21), 137 (19). Approximately 50 Mg of 17 was dissolved in CH2C12 (0.1 mL) containing pyridine (5 mL).…”

Section: T H I S C O N T E N T Imentioning

confidence: 99%

“…226 nm; EIMS, m/z, (relative intensity) 536 (M+, 7), 518 (8), 448 (22), 409 (48), 388 (22), 350 (13), 307 (19), 295 (16), 185 (24), 184 (100), 173 (30), 155 (30), 137 (20), 125 (18).…”

Section: T H I S C O N T E N T Imentioning

confidence: 99%

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Structure determination of oligomycins A and C

Carter¹

1986

J. Org. Chem.

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Section: Methodsmentioning

confidence: 99%

Section: T H I S C O N T E N T Imentioning

confidence: 99%

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Structure determination of oligomycins A and C

Carter¹

1986

J. Org. Chem.

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The structural elucidation of polyene macrolide antibiotics by mass spectrometry. Nystatin, amphotericin B and pimaricin

Haegele

Desiderio

1974

Biol. Mass Spectrom.

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Complete mass spectra of the pertrimethylsilylated derivatives of three high molecular weight polyene macrolide antibiotics are reported for the first time. The fragmentation pathways which are proposed have been corroborated by the stable isotope derivatives d,-TMS and d,-acetyl. Accurate mass measurements and metastable transitions confirm the proposed fragmentation mechanisms in the low mass range. Nystatin-the macrolide of highest molecular weight in this study --expels several TMSOH molecules and a TMS radical. Amphotericin B underwent extensive rearrangements preliminary to eliminating a series of TMSOH molecules. An apparent equilibrium between the keto and ketal forms of amphotericin B facilitated the rearrangements. Pimaricin fragmented in a manner parallel to that of the other two macrolides. The sugar portion of the molecules dominated the fragmentation in the low mass region in the spectra of all compounds. The transfer of a TMS group from the sugar amine to the glycosidic oxygen was observed when the amino sugar was eliminated from the intact molecule. The resulting sugar ion then expelled ammonia.

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Stoffwechselprodukte von Mikroorganismen 227. Mitteilung. Isolierung und Strukturaufklärung von Rutamycin B

Wuthier

Keller‐Schierlein

Wahl

1984

Helvetica Chimica Acta

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SummaryBotrycidin was found to be identical with rutamycin. From the cultures of the actinomycete producing botrycidin and the venturicidines A and B, a fourth antifungal antibiotic, rutamycin B, was isolated. Through a series of degradation products its structure could be correlated to that of rutamycin, which had been determined before by an X-ray structural analysis. Rutamycin B has been identified as 12-deoxyrut am ycin .

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Characterization of the oligomycins and related antibiotics

Cited by 22 publications

References 4 publications

Structure determination of oligomycins A and C

Structure determination of oligomycins A and C

The structural elucidation of polyene macrolide antibiotics by mass spectrometry. Nystatin, amphotericin B and pimaricin

Stoffwechselprodukte von Mikroorganismen 227. Mitteilung. Isolierung und Strukturaufklärung von Rutamycin B

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