Oligomycin

Oligomycin A

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
CAS number	1404-19-9
PubChem	6450197
ChemSpider	21106358^Y
EC number	215-767-9
MeSH	Oligomycins
RTECS number	RK3325000
Jmol-3D images	Image 1
SMILES 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
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/s1^Y Key: QBAMBSAJEFIQBK-GJHUHQBXSA-N^Y
Properties
Molar mass	791.062 g/mol
Hazards
MSDS	MSDS at Fermentek
Y (verify) (what is: Y/N?) 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 (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**^[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

^ 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.