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Oligomycin

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Oligomycin A
Names
IUPAC name (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'--5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3H,9H,13H-spirononacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione
Other names Oligomycin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.334 Edit this at Wikidata
EC Number
  • 215-767-9
MeSH Oligomycins
PubChem CID
RTECS number
  • RK3325000
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C46H76O11/c1-13-34-18-16-14-15-17-28(4)42(51)45(12,54)43(52)32(8)40(50)31(7)39(49)30(6)38(48)27(3)19-22-37(47)55-41-29(5)35(21-20-34)56-46(33(41)9)24-23-26(2)36(57-46)25-44(10,11)53/h14-16,18-19,22,26-36,38,40-42,48,50-51,53-54H,13,17,20-21,23-25H2,1-12H3/b15-14+,18-16-,22-19+/t26-,27-,28+,29+,30+,31-,32-,33-,34+,35?,36-,38-,40+,41+,42+,45+,46-/m1/s1Key: QBAMBSAJEFIQBK-GJHUHQBXSA-N
  • Key: QBAMBSAJEFIQBK-GJHUHQBXBC
  • Key: QBAMBSAJEFIQBK-GJHUHQBXSA-N
SMILES
  • C(C)(O)C1O2(CC1C)O3CC(CC)/C=C\C=C\C(C)(O)(C)(O)C(=O)(C)(O)(C)C(=O)(C)(O)(C)/C=C/C(=O)O(2C)3C
Properties
Molar mass 791.062 g/mol
Supplementary data page
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Oligomycins are macrolides created by Streptomyces that can be poisonous to other organisms.

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.

Oligomycin is an inhibitor of ATP synthase. In oxidative phosphorylation research, it is used to prevent state 3 (phosphorylating) respiration.

Oligomycins
  R R R R R
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

References

  1. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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