Oligomycin




































































Oligomycin A

Oligomycin.png
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

CAS Number

  • 1404-19-9 ☑Y

3D model (JSmol)
  • Interactive image

ChEBI
  • CHEBI:28285

ChemSpider

  • 21106358 ☑Y

EC Number
 215-767-9

MeSH
Oligomycins


PubChem CID
  • 6450197

RTECS number
 RK3325000




Properties

Chemical formula
C45H74O11

Molar mass
 791.062 g/mol
Hazards

Safety data sheet
MSDS at Fermentek

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


☑Y verify (what is ☑Y☒N ?)

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 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]

Oligomycins.png
 
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. ^ Jastroch M, Divakaruni AS, Mookerjee S, Treberg JR, Brand MD (2010). "Mitochondrial proton and electron leaks". Essays in biochemistry. 47 (1): 53–67. doi:10.1042/bse0470053. PMC 3122475. PMID 20533900..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"""""""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  2. ^ 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.









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