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Question: The total degradation of a fatty acid with an odd number of

carbons yields acetyl-CoA and another compound, X. Show the structure of


X, and describe the pathway by which it is converted into a citric acid cycle
intermediate. including where any cofactors participate.
Answer: X is propionyl-CoA, CH3CH2C0CoA
The structure and reaction pathway are shown in the attachments.
Explanation: In the oxidation of odd-number fatty acids, the substrate for
the last pass through beta-oxidation is fatty acyl-CoA with  a five-carbon
fatty acid. This is oxidized and cleaved to acetyl-CoA and propionyl-
CoA. Acetyl-CoA enters the citric acid cycle while the propionyl-CoA is
converted in three enzymatic steps to succinyl-CoA which can then enter
the citric acid cycle.
Step 1: Conversion of propionyl-CoA to D-methylmalonyl-CoA
Propionyl-CoA is carboxylated to D-methylmalonyl-CoA by the
enzyme propionyl-CoA carboxylase, which contains the cofactor biotin. A
molecule of ATP and Carbon (iv) oxide (in the form of hydrogen
carbonate ion) is required also.
Step 2: Epimerization of D-methylmalonyl-CoA
D-methylmalonyl-CoA is epimerized by the enzyme methylmalonyl-Co
epimerase to its L stereoisomer, L-methylmalonyl-CoA.
Step 3: Conversion of L-methylmalonyl-CoA to succinyl-CoA
This reaction is catalysed by methylmalonyl-CoA mutase which requires
the coenzyme B12.

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