| 词条 | Propionyl-CoA |
| 释义 |
| Verifiedfields = changed | verifiedrevid = 464216740 | ImageFile = Propionyl-Coenzyme A.png | ImageSize = 250px | IUPACName = S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] propanethioate | OtherNames = Propionyl Coenzyme A; Propanoyl Coenzyme A |Section1={{Chembox Identifiers | InChI1 = 1/C24H40N7O17P3S/c1-4-15(33)52-8-7-26-14(32)5-6-27-22(36)19(35)24(2,3)10-45-51(42,43)48-50(40,41)44-9-13-18(47-49(37,38)39)17(34)23(46-13)31-12-30-16-20(25)28-11-29-21(16)31/h11-13,17-19,23,34-35H,4-10H2,1-3H3,(H,26,32)(H,27,36)(H,40,41)(H,42,43)(H2,25,28,29)(H2,37,38,39)/t13?,17-,18-,19?,23?/m1/s1 | InChIKey1 = QAQREVBBADEHPA-HOMDEXLGBF | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C24H40N7O17P3S/c1-4-15(33)52-8-7-26-14(32)5-6-27-22(36)19(35)24(2,3)10-45-51(42,43)48-50(40,41)44-9-13-18(47-49(37,38)39)17(34)23(46-13)31-12-30-16-20(25)28-11-29-21(16)31/h11-13,17-19,23,34-35H,4-10H2,1-3H3,(H,26,32)(H,27,36)(H,40,41)(H,42,43)(H2,25,28,29)(H2,37,38,39)/t13?,17-,18-,19?,23?/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = QAQREVBBADEHPA-HOMDEXLGSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 317-66-8 | PubChem = 439164 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 21106467 | SMILES = CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC3OC(n2cnc1c(N)ncnc12)[C@H](O)[C@@H]3OP(O)(O)=O | MeSHName = propionyl-coenzyme+A |Section2={{Chembox Properties | Formula = C24H40N7O17P3S | MolarMass = 823.60 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} Propionyl-CoA is a coenzyme A derivative of propionic acid. Metabolism in animalsProductionThere are several different ways in which it is formed:
Metabolic fateIn mammals, propionyl-CoA is converted to (S)-methylmalonyl-CoA by propionyl-CoA carboxylase, a biotin-dependent enzyme also requiring bicarbonate and ATP. This product is converted to (R)-methylmalonyl-CoA by methylmalonyl-CoA racemase. (R)-Methylmalonyl-CoA is converted to succinyl-CoA, an intermediate in the tricarboxylic acid cycle, by methylmalonyl-CoA mutase, an enzyme requiring cobalamin to catalyze the carbon-carbon bond migration. The methylmalonyl-CoA mutase mechanism begins with the cleavage of the bond between the 5' {{chem|C|H|2}}- of 5'-deoxyadenosyl and the cobalt, which is in its 3+ oxidation state (III), which produces a 5'-deoxyadenosyl radical and cobalamin in the reduced Co(II) oxidation state. Next, this radical abstracts a hydrogen atom from the methyl group of methylmalonyl-CoA, which generates a methylmalonyl-CoA radical. It is believed that this radical forms a carbon-cobalt bond to the coenzyme, which is then followed by the rearrangement of the substrate's carbon skeleton, thus producing a succinyl-CoA radical. This radical then goes on to abstract a hydrogen from the previously produced 5'-deoxyadenosine, again creating a deoxyadenosyl radical, which attacks the coenzyme to reform the initial complex. A defect in methylmalonyl-CoA mutase enzyme results in methylmalonic aciduria, a dangerous disorder that causes a lowering of blood pH. Metabolism in plants and insectsIn plants and insects propionyl-CoA is metabolized to acetate in a very different way, similar to beta-oxidation. Not all details of this pathway have been worked out, but it appears to involve formation of acrylyl-CoA, then 3-hydroxypropionyl-CoA. This is metabolized with loss of carbon 1 of 3-hydroxypropionyl-CoA as carbon dioxide, while carbon 3 becomes carbon 1 of acetate. References
2 : Thioesters of coenzyme A|Metabolism |
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