Oligomycin

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Oligomycin A
200px
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'-[(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
Other names
Oligomycin
Identifiers
1404-19-9 YesY
ChemSpider 21106358 YesY
EC Number 215-767-9
Jmol 3D model Interactive image
MeSH Oligomycins
PubChem 6450197
RTECS number RK3325000
  • 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/s1 YesY
    Key: QBAMBSAJEFIQBK-GJHUHQBXSA-N YesY
  • 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/s1
    Key: QBAMBSAJEFIQBK-GJHUHQBXBC
  • Key: QBAMBSAJEFIQBK-GJHUHQBXSA-N
  • C[C@](C)(O)C[C@H]1O[C@@]2(CC[C@H]1C)O[C@H]3CC[C@@H](CC)/C=C\C=C\C[C@H](C)[C@H](O)[C@](C)(O)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@@H](C)[C@H](O)[C@H](C)/C=C/C(=O)O[C@H]([C@H]2C)[C@H]3C
Properties
C45H74O11
Molar mass 791.062 g/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

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

Function

They have use as antibiotics.

Oligomycin A is an inhibitor of ATP synthase. In oxidative phosphorylation research, it is used to prevent state 3 (phosphorylating) respiration. Oligomycin A 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 by oligomycin A will significantly reduce electron flow through the electron transport chain; however, electron flow is not stopped completely due to a process known as proton leak or mitochondrial uncoupling.[1] This process is due to the facilitated diffusion of protons into the mitochondrial matrix through an uncoupling protein such as thermogenin, or UCP1.

Administering oligomycin to an individual can result in very high levels of lactate accumulating in the blood and urine.[citation needed]

Oligomycins[2]
200px
  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

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it:Fosforilazione ossidativa#Inibitori

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  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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