An 8-week intermediate organic laboratory is detailed for the solid-phase synthesis of cyclic, cysteine-containing, depsipeptidic potential anticancer compounds. These compounds, which belong to a class of HDAC inhibitors, were accessed using a novel latent thioester solid-phase linker. The target depsipeptides are intended as potential treatments for cancer and other ailments implicating HDAC, and can also be used to evaluate the influence of various residue side chains on HDAC binding. This laboratory includes the first attempts to synthesize some of these synthetic targets, and therefore embodies a significant, original research project. The effects of incorporating this type of research into the laboratory component of an organic chemistry course are evaluated in terms of student engagement and learning outcomes.

Incorporating original research into the organic teaching laboratory: The HDACi cancer therapeutic laboratory project

245th National Meeting (2013)

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