Azole-rich oligoamide macrocycles are found as a variety of peptide-derived natural products including dendroamide and patellamides. A desire to replicate and/or modulate the biological activities of the natural products motivates the development of new methods to access diverse synthetic analogs for application and study. We have developed efficient synthetic methods to access N-substituted azole-containing amino esters as important building blocks for preparation of new peptidomimetics. N-substituents have been widely varied to introduce a range of functionality. Additionally, we have identified methods for the preparation of macrocycles that contain these building blocks and emulate natural product structures. Structural studies of the macrocycles in solution and in the solid state have revealed the influences of the azole identity, N-substituent, and ring size on the conformation of the ring. These findings will guide future applications of these new peptidomimetic molecules.

Synthesis and structural studies of peptidomimetic N-substituted azole-rich macrocycles

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.