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Metal-Binding Q-Proline Macrocycles

preprint
submitted on 11.01.2021, 18:43 and posted on 12.01.2021, 12:47 by Justin Northrup, Jesse Wiener, Matthew Hurley, Chun-Feng David Hou, Taylor Keller, Richard Baxter, Michael J. Zdilla, Vincent Voelz, Christian Schafmeister
Herein, we introduce the efficient synthesis of Q-proline (Q-Pro) based, metal-binding macrocycles (QPM), which can display up to nine functional groups. Synthesis of eight QPM was achieved through standard Fmoc-SPPS and peptoid chemistry. QPM are disordered in the absence of a metal cation, as evidenced by NMR and a crystal structure of QPM-3 obtained through racemic crystallization. Addition of metal cations cause these macrocycles to adopt ordered, uniform core structures regardless of the functional groups. Alkylation of QPM allows for addition of reactive functional groups as the final step in a synthesis. Interestingly, the addition of secondary functional groups to the hydantoin amide position (R2) converts the proline ring from Cg-endo to Cg-exo, due to steric interactions.

Funding

HDTRA1-16-1-0047

1R01GM123296

1R01GM114358

NSF 1625061

W911NF-16-2-0189

History

Email Address of Submitting Author

jdn@temple.edu

Institution

Temple University

Country

United States of America

ORCID For Submitting Author

0000-0001-6325-4946

Declaration of Conflict of Interest

no conflict of interest

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