Metal-Binding Q-Proline Macrocycles.
J Org Chem
; 86(6): 4867-4876, 2021 03 19.
Article
de En
| MEDLINE
| ID: mdl-33635647
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.
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Sujet principal:
Proline
Langue:
En
Journal:
J Org Chem
Année:
2021
Type de document:
Article
Pays d'affiliation:
États-Unis d'Amérique