Which step in lipid metabolism would you expect to be affected by 3,4-dihydroxybutyl-1-phosphonic acid? Explain.

Expert Solution

Simple answer is : The esterification of glycerol-3-phosphate with fatty acyl-CoA, catalyzed by glycerophosphate acyltransferase. 3,4-Dihydroxybutyl-1-phosphonic acid binds to glycerol-3-phosphate.

Explanation:

Glycerol-3-phosphate is acylated with fatty acyl-CoA by enzyme glycerophosphate acyltransferase. It is also formed by ATP-dependent phosphorylation of glycerol by glycerokinase and by gluconeogenesis. This latter source appear to be of quantitative importance only in the liver. Fatty acid is first esterified with Coenzyme A by the enzyme acyl-CoA synthestase, as only the CoA thioesters of fatty acids serve as substrates for acylation reactions in mammalian cells. Acylation of 1-acyl-glycerol-3-phosphate with a second fatty acyl-CoA by the enzyme 1-acylglycerophosphate acyl-transferase produces phosphatidic acid. In liver glycerophosphate acyl-transferase activity is distributed evenly between mitochondrial and microsomal compartments. In other tissues, such as adipose,heart,kidney,brain and adrenal tissue, the microsomal activity is several times that found in mitochondria, suggesting that in general the microsomal acylation reactions have the responsibility for producing physiologically important amounts of phosphatidic acid for glycerolipid biosynthesis.

Since this is a nonhydrolyzable analog of glycerol-3-phosphate, so it is acylated without difficulty to give the phosphonate analog of diacylglycerol.

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