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US 4,375,462 AGranted
A-32724 Antibiotics and process for production thereof
AssigneeEli Lilly and Company
InventorsDavid H. Berg, Marvin M. Hoehn
Life of this patent
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Abstract
Antibiotic A-32724 complex, comprising microbiologically-active, related factors A, B and C, is produced by submerged, aerobic fermentation of a strain of Chaetomella raphigera Swift NRRL 12331. The A-32724 antibiotics are closely related antibiotics. The individual A-32724 factors are separated by chromatography. In addition to their antibacterial activity, the A-32724 factors inhibit certain enzymes and exhibit antihypertensive properties.
Claims2
Antibiotic A-32724 Factor A having the following physical and chemical properties:
- (1) Melting point of about 175.degree.-176.degree. C. (dec.);
- (2) Molecular weight 738 (determined by nuclear magnetic resonance spectrum, sulfate determination, and field-desorption and electron-impact mass spectrometry);
- (3) Ultraviolet absorption spectrum in aqueous solution having absorption maxima at 265 nm (.epsilon.=333), and 271 nm (sh) (.epsilon.=252);
- (4) Infrared absorption spectrum shown in FIG. 1 as measured by KBr pellet method and having the following distinguishable absorption maxima:
- 3426 (strong), 2923 (strong), 2852 (strong), 1736 (medium), 1720 (medium), 1616 (medium), 1590 (medium), 1458 (medium), 1383 (shoulder), 1375 (medium weak), 1241 (very strong), 1123 (weak), 1068 (strong), 981 (strong), 884 (weak), 865 (weak), 625 (weak), and 581 cm..sup.-1 (weak);
- (5) Proton magnetic resonance spectrum in DMSO-d.sub.6, at 100 MHz, using internal TMS as reference, as follows:
- ______________________________________ Resonance Chemical No. of Description Shift .delta., ppm Protons ______________________________________ Triplet 6.80 1 Doublet 6.74 2 Multiplet 4.67 1 Doublet 4.60 1 (exchangeable) Multiplet 3.40 1 Triplet .about.2.5 Overlapped with solvent Singlet 1.97 3 Multiplet .about.1.5 42 Broad singlet 1.23 Triplet 0.84 3 ______________________________________
- (6) .sup.13 C Nuclear magnetic resonance spectrum, in DMSO-d.sub.6, using internal TMS as reference, showing chemical shifts, expressed in parts per million, as follows:
- ______________________________________ No. PPM ______________________________________ 1 170.0 2 153.4 3 142.7 4 115.1 5 110.4 6 75.8 7 70.8 8 35.2 9 32.2 10 31.2 11 30.9 12 29.3 13 29.0 14 28.7 15 28.5 16 25.1 17 25.0 18 22.1 19 20.8 20 13.9 ______________________________________
- (7) Solubility to solvent:
- Soluble in water and methanol;
- (8) Color and form of substance:
- Amorphous white powder;
- and
- (9) An empirical formula of C.sub.33 H.sub.56 O.sub.11 S.sub.2 Na.sub.2.
12 more elements
Antibiotic A-32724 Factor B having the following physical and chemical properties:
- (1) Melting point of about 160.degree.-162.degree. C. (dec.);
- (2) Molecular weight 738 (determined by nuclear magnetic resonance spectrum, sulfate determination, and field-desorption and electron-impact mass spectrometry);
- (3) Ultraviolet absorption spectrum in water solution having absorption maxima at 265 nm (.epsilon.=321), and 271 nm (sh) (.epsilon.=249);
- (4) Infrared absorption spectrum shown in FIG. 2 as measured by KBr pellet method and having the following distinguishable absorption maxima:
- 3468 (strong), 3452 (strong), 2923 (strong), 2853 (strong), 1733 (medium), 1616 (medium), 1591 (medium weak), 1455 (medium), 1376 (weak), 1242 (very strong), 1124 (weak), 1068 (strong), 1032 (shoulder), 980 (strong), 905 (weak), 795 (medium), 767 (medium weak), 721 (weak), 684 (weak), 670 (shoulder), 662 (shoulder), 617 (medium weak), and 579 cm..sup.-1 (medium);
- (5) Proton magnetic resonance spectrum in DMSO-d.sub.6, at 100 MHz, using internal TMS as reference, as follows:
- ______________________________________ Resonance Chemical No. of Description Shift .delta., ppm Protons ______________________________________ Triplet 6.78 1 Doublet 6.73 2 Multiplet 4.95 1 Multiplet 4.08 1 Triplet .about.2.5 Overlapped with solvent Singlet 1.98 3 Multiplet .about.1.5 .about.40 Broad singlet 1.23 Triplet 0.85 3 ______________________________________
- (6) .sup.13 C Nuclear magnetic resonance spectrum, in DMSO-d.sub.6, using internal TMS as reference, showing chemical shifts, expressed in parts per million, as follows:
- ______________________________________ No. PPM ______________________________________ 1 169.8 2 153.4 3 142.7 4 115.1 5 110.3 6 75.9 7 72.8 8 62.9 9 41.1 10 40.2 11 39.4 12 33.5 13 37.7 14 35.2 15 31.2 16 30.8 17 29.9 18 29.0 19 25.0 20 24.5 21 22.0 22 20.7 23 13.9 24 0.0 ______________________________________
- (7) Solubility to solvent:
- Soluble in water and methanol;
- (8) Color and form of substance:
- Amorphous white powder;
- and
- (9) An empirical formula of C.sub.33 H.sub.56 O.sub.11 S.sub.2 Na.sub.2.
12 more elements
Dependencies are inferred from the claim text.