Oligomycin

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.^{[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

^ 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.

Categories:
Macrolide antibiotics

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**^[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

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Look at other dictionaries:

oligomycin sensitivity conferral protein — (= OSCP) The d subunit of the ATP synthase, believed to link the F 1 catalytic segment to the F f573 sfo proton conduction segment. Binds the toxin oligomycin … Dictionary of molecular biology
oligomycin — A bacterial toxin inhibitor of oxidative phosphorylation that acts on a small subunit of the F1 ATPase … Dictionary of molecular biology
oligomycin — oli·go·my·cin .äl i gō mīs ən, .ō li n any of several antibiotic substances produced by an actinomycete of the genus Streptomyces (S. diastatochromogenes or a closely related species) and used esp. in biochemical research to inhibit oxidative… … Medical dictionary
oligomycin — oli·go·my·cin … English syllables
oligomycin — n. antibiotic used against plant fungi … Dictionary of difficult words
oligomycin — ˌäligōˈmīsən, ˌōli noun ( s) Etymology: olig + mycin : any of several antibiotic substances produced by a streptomyces (of a species similar to Streptomyces diastatochromogenes) and used especially in biochemical research to inhibit oxidative… … Useful english dictionary
Oligomicina — Oligomycin A Nombre (IUPAC) sistemático n/d … Wikipedia Español
OMR — oligomycin resistant; online medical record … Medical dictionary
OMR — • oligomycin resistant; • online medical record … Dictionary of medical acronyms & abbreviations
Oxidative phosphorylation — The electron transport chain in the mitochondrion is the site of oxidative phosphorylation in eukaryotes. The NADH and succinate generated in the citric acid cycle are oxidized, releasing energy to power the ATP synthase. Oxidative… … Wikipedia

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Oligomycin

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