Propionyl Coenzyme A; Propanoyl Coenzyme A
3D model (JSmol)
|Molar mass||823.60 g/mol|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Metabolism in animals
There are several different ways in which it is formed:
- It is formed as a product of beta-oxidation of odd-chain fatty acids.
- It is also a product of metabolism of isoleucine and valine.
- It is a product of alpha-ketobutyric acid, which in turn is a product of catabolism of threonine and methionine.
- It is formed as a by-product during the conversion of cholesterol to bile acids.
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' CH
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 insects
In plants and insects propionyl-CoA is metabolized to acetate in a very different way, similar to beta-oxidation.
This is metabolized with loss of carbon 1 of 3-hydroxypropionyl-CoA as carbon dioxide, while carbon 3 becomes carbon 1 of acetate.