TY - JOUR
T1 - Metal-Binding Q-Proline Macrocycles
AU - Northrup, Justin D.
AU - Wiener, Jesse A.
AU - Hurley, Matthew F.D.
AU - Hou, Chun Feng David
AU - Keller, Taylor M.
AU - Baxter, Richard
AU - Zdilla, Michael J.
AU - Voelz, Vincent
AU - Schafmeister, Christian E.
N1 - Publisher Copyright:
©
PY - 2021/3/19
Y1 - 2021/3/19
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/85103329692
U2 - 10.1021/acs.joc.1c00116
DO - 10.1021/acs.joc.1c00116
M3 - Article
SN - 0022-3263
VL - 86
SP - 4867
EP - 4876
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 6
ER -