Oligomycin
| Oligomycin A | |
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(1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione |
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Other names
Oligomycin |
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| Identifiers | |
| CAS number | 1404-19-9 |
| PubChem | 6450197 |
| ChemSpider | 21106358  |
| EC number | 215-767-9 |
| MeSH | Oligomycins |
| RTECS number | RK3325000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molar mass | 791.062 g/mol |
| Hazards | |
| MSDS | MSDS at Fermentek |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Oligomycins are macrolides created by Streptomyces that can be poisonous to other organisms.
[edit] Function
They have use as antibiotics.
In addition, oligomycin inhibits ATP synthase by blocking its proton channel (Fo subunit), which is necessary for oxidative phosphorylation of ADP to ATP (energy production). The inhibition of ATP synthesis would also stop electron transport chain. Because the high proton concentration build up is not dissipated, the free energy released by biological oxidation of substrates is not enough to pump any more protons against the steep gradient.
Administering oligomycin to an individual can result in very high levels of lactate accumulating in the blood and urine.[citation needed]
Oligomycin is an inhibitor of ATP synthase. In oxidative phosphorylation research, it is used to prevent state 3 (phosphorylating) respiration.
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| R1 | R2 | R3 | R4 | R5 | |
| Oligomycin A | CH3 | H | OH | H,H | CH3 |
| Oligomycin B | CH3 | H | OH | O | CH3 |
| Oligomycin C | CH3 | H | H | H,H | CH3 |
| Oligomycin D (Rutamycin A) |
H | H | OH | H,H | CH3 |
| Oligomycin E | CH3 | OH | OH | O | CH3 |
| Oligomycin F | CH3 | H | OH | H,H | CH2CH3 |
| Rutamycin B | H | H | H | H,H | CH3 |
| 44-Homooligomycin A | CH2CH3 | H | OH | H,H | CH3 |
| 44-Homooligomycin B | CH2CH3 | H | OH | O | CH3 |
[edit] References
- ^ Nakata, Masaya; Ishiyama, Takashi; Akamatsu, Shinichi; Hirose, Youichi; Maruoka, Hiroshi; Suzuki, Rika; Tatsuta, Kuniaki (1995). "Synthetic studies on oligomycins. Synthesis of the oligomycin B spiroketal and polypropionate portions". Bulletin of the Chemical Society of Japan 68 (3): 967–89. doi:10.1246/bcsj.68.967.
