Add time:09/24/2019         Source:sciencedirect.com

Publisher SummaryThis chapter discusses the chemical synthesis of lactyl CoA, malonyl CoA, and β-ketoöctanoyl CoA. These three compounds are examples of CoA thiolesters that are difficult or impossible to synthesize by the usual thiolester preparative procedures because of interference by α-hydroxy, α-carboxy, or β-keto functional groups, respectively. The method for synthesis of lactyl CoA is based on the fact that an α-hydroxy acid reacts with phosgene to form the acid chloride. The acid chloride readily reacts with thiophenol to yield the acyl thiophenyl ester, which is used to acylate CoA. The method for synthesis of malonyl CoA via mixed anhydride of malonic and acetic acids is based on the fact that ketene reacts with malonic acid in ether to form a mixed anhydride of malonic and acetic acids. The mixed anhydride reacts with thiophenol to give malonylthiophenyl ester, which is used to acylate CoASH. The method for synthesis of β-ketoöctanoyl CoA is based on the fact that the keto group of an ethyl ester of a β-keto acid can be blocked by converting it to an ethyleneketal. The ethyleneketal derivative is converted to a thiolester of thioglycolic acid. The keto function is regenerated by treating the thiolester with sulfuric acid. β-ketoacyl CoA is then formed by an ester interchange reaction between β-ketoacyl-S-thioglycolate and CoASH.

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