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Northrup JD , Wiener JA , Hurley MFD , Hou CD , Keller TM , Baxter RHG , Zdilla MJ , Voelz VA , Schafmeister CE
Metal-Binding Q-Proline Macrocycles
J Org Chem. 2021 Mar 19;86(6) :4867-4876
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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 (R(2)) converts the proline ring from Cγ-endo to Cγ-exo, due to steric interactions.
Notes
1520-6904 Northrup, Justin D Orcid: 0000-0001-6325-4946 Wiener, Jesse A Hurley, Matthew F D Hou, Chun-Feng David Keller, Taylor M Baxter, Richard H G Orcid: 0000-0001-5140-1726 Zdilla, Michael J Orcid: 0000-0003-0212-2557 Voelz, Vincent A Orcid: 0000-0002-1054-2124 Schafmeister, Christian E Orcid: 0000-0002-8686-7363 Journal Article United States J Org Chem. 2021 Mar 19;86(6):4867-4876. doi: 10.1021/acs.joc.1c00116. Epub 2021 Feb 26.