Metal-Binding Q‑Proline Macrocycles

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. Up...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 86; no. 6; pp. 4867 - 4876
Main Authors Northrup, Justin D, Wiener, Jesse A, Hurley, Matthew F. D, Hou, Chun-Feng David, Keller, Taylor M, Baxter, Richard H. G, Zdilla, Michael J, Voelz, Vincent A, Schafmeister, Christian E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.03.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
crystal structure
crystallization
N-substituted glycines
organic chemistry
Physical Sciences
proline
Science & Technology
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.1c00116