J Org Chem. 2021 Mar 19;86(6):4867-4876. doi: 10.1021/acs.joc.1c00116. Epub 2021 Feb 26.
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.
PMID:33635647 | DOI:10.1021/acs.joc.1c00116