Metal-Binding Q-Proline Macrocycles

Authors:
Publisher website
Google Scholar
Abstract
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.
Funding Information
  • Defense Threat Reduction Agency (HDTRA1-16-1-0047)
  • Army Research Laboratory (W911NF-16-2-0189)
  • National Institute of General Medical Sciences (1R01GM114358, 1R01GM123296)

This publication has 26 references indexed in Scilit: