Metal-Binding Q-Proline Macrocycles
| Autor: | Justin D. Northrup, Vincent A. Voelz, Richard H. G. Baxter, Christian E. Schafmeister, Michael J. Zdilla, Taylor Keller, Chun-Feng David Hou, Matthew F. D. Hurley, Jesse A Wiener |
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| Rok vydání: | 2021 |
| Předmět: |
Steric effects
Models Molecular Magnetic Resonance Spectroscopy Proline Hydantoin Crystal structure Alkylation 010402 general chemistry 01 natural sciences law.invention Metal chemistry.chemical_compound law Amide Crystallization 010405 organic chemistry Organic Chemistry Peptoid Nuclear magnetic resonance spectroscopy 0104 chemical sciences Crystallography chemistry visual_art Functional group visual_art.visual_art_medium |
| Zdroj: | The Journal of organic chemistry. 86(6) |
| ISSN: | 1520-6904 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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