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
EC number	215-767-9
MeSH	Oligomycins
RTECS number	RK3325000
SMILES	C[C@@H](O)C[C@@H]1O[C@]3(CC[C@@H]1C)O[C@H]2CC[C@@H](CC)C=CC=CC[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=CC(=O)O[C@H]([C@@H]2C)[C@@H]3C
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 continues 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