Metal-Binding Q-Proline Macrocycles.
Justin D NorthrupJesse A WienerMatthew F D HurleyChun-Feng David HouTaylor M KellerRichard H G BaxterMichael J ZdillaVincent A VoelzChristian E SchafmeisterPublished in: The Journal of organic chemistry (2021)
We introduce the efficient Fmoc-SPPS and peptoid synthesis of Q-proline-based, metal-binding macrocycles (QPMs), which bind metal cations and display nine functional groups. Metal-free QPMs are disordered, evidenced by NMR and a crystal structure of QPM-3 obtained through racemic crystallization. Upon addition of metal cations, QPMs adopt ordered structures. Notably, the addition of a second functional group at the hydantoin amide position (R2) converts the proline ring from Cγ-endo to Cγ-exo, due to steric interactions.