Stercobilin has been implicated as a potential biomarker for childhood autism. Researchers at the University of Buffalo have discovered that in the urine of autistic children there is ten times lower amounts of stercobilin than that of the controls. The purpose of this project is to synthesize an isotopically labeled stercobilin molecule from bilirubin in a two step process, including hydrogenation followed by oxidation. Initial IR, NMR and LCMS analysis indicates that the stercobilin product is not completely labeled with deuterium during the hydrogenation step. We report here the results of a complete comparison of the products obtained using the three following different reactions conditions; H2 with glacial acetic acid, D2 with glacial acetic acid, and D2 with deuterated acetic acid. These results provide insight into the reaction mechanisms involved in these three different hydrogenation reactions.

Synthesis of stercobilin: A potential biomarker for autism

245th National Meeting (2013)

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