Thioesters are similar to the more commonly found oxoesters, except they have a sulfur atom in place of an oxygen atom in the leaving group position. They are a very important class of reactive carboxylic acid derivatives used in both chemistry and biochemistry. The uncatalyzed and enzyme catalyzed hydrolysis reaction of the thioester, formylthiocholine, was investigated. The novel thioester substrate was synthesized in two steps from 2-(N,N-dimethylamino)-ethanethiol and the rate of formylthiocholine hydrolysis under alkaline conditions was studied. The thioester was also used as a substrate analog for enzymatic hydrolysis by acetylcholinesterase (AChE). The enzymatic kinetic data (Km and kcat/Km) for formylthiocholine was compared to another thioester-containing substrate, thioacetylcholine.

Formylthiocholine: Synthesis and comparison of catalyzed vs. uncatalyzed thioester hydrolysis reactions

241st National Meeting (2011)

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