In recent years, S-adenosyl-L-homocysteine (AdoHcy) analogues that inhibit the action of AdoHcy hydrolase have been a target of pharmaceutical drug design due to AdoHcy's potent feedback inhibition of transmethylation enzymes. The goal of this research is to model an efficient, two step synthesis route for AdoHcy analogues using a variety of aryl aldehydes and ketones. The first step involves a modified Ramirez procedure to perform a Wittig reaction, where different reagents and procedures were screened to optimize yields. The second step involves a cross coupling reaction (similar to a Negishi cross coupling reaction) that utilizes micellular nanoreactors in a water based solvent to provide a catalytic environment. For this step, different types of zinc, alkyl bromides, and molar ratios of reagents were used to find optimal reaction conditions.

Studies toward metal-mediated synthesis of S-adenosyl-L-homocysteine analogs

245th National Meeting (2013)

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