Oligomycin
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Oligomycin"
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Oligomycin A
Other names Oligomycin
Molecular formula C45H74O11
Identifiers
CAS number [1404-19-9]
PubChem 6450197
EINECS number 215-767-9
MeSH Oligomycins
RTECS number RK3325000
Properties
Molar mass 791.062 g/mol
Hazards
MSDS MSDS at Fermentek
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox references

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, which is necessary for oxidative phosphorylation of ADP to ATP (energy production). Electron transport stops but there is an increase in the proton gradient, and electron transport soon stops because of the difficulty of pumping 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.


Oligomycins[1]
  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


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. 
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