Peptoids, or N-substituted glycines, are non-natural peptidomimetic polymers that are easy to control in sequence and are resistant to degradation. Their nanoscale behavior, such as supramolecular assembly and folding into higher order structures, as well as their bioactivity in numerous applications have been reported. The current standard condition in synthesizing peptoids by the submonomer method works well for most primary amines. However, the limitation of this method is evident when incorporating electron-deficient amine submonomers as coupling yields drop and extended reaction times are needed. Herein, we report a significant acceleration in the incorporation electron-deficient submonomers by the inclusion of heavy metal salts in the displacement step. This method opens up new families of monomers that can be incorporated into peptoids in a time-efficient manner, thus significantly expanding the versatility and applicability of peptoids. With this method, we synthesized aniline-rich, amphiphilic peptoids, whose ability to form peptoid nanosheet bilayers were investigated.

Improved synthesis of peptoids with electron-deficient side chains and their application in controlling chain conformation

248th National Meeting (2014)

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