Wienands, Laura ; Theiß, Franziska ; Eills, James ; Rösler, Lorenz ; Knecht, Stephan ; Buntkowsky, Gerd (2021)
Optimizing the Reaction Conditions for the Formation of Fumarate via Trans-Hydrogenation.
In: Applied Magnetic Resonance, 53 (3)
doi: 10.1007/s00723-021-01371-w
Article, Bibliographie
This is the latest version of this item.
Abstract
Parahydrogen-induced polarization is a hyperpolarization method for enhancing nuclear magnetic resonance signals by chemical reactions/interactions involving the para spin isomer of hydrogen gas. This method has allowed for biomolecules to be hyperpolarized to such a level that they can be used for real time in vivo metabolic imaging. One particularly promising example is fumarate, which can be rapidly and efficiently hyperpolarized at low cost by hydrogenating an acetylene dicarboxylate precursor molecule using parahydrogen. The reaction is relatively slow compared to the timescale on which the hyperpolarization relaxes back to thermal equilibrium, and an undesirable 2nd hydrogenation step can convert the fumarate into succinate. To date, the hydrogenation chemistry has not been thoroughly investigated, so previous work has been inconsistent in the chosen reaction conditions in the search for ever-higher reaction rate and yield. In this work we investigate the solution preparation protocols and the reaction conditions on the rate and yield of fumarate formation. We report conditions to reproducibly yield over 100 mM fumarate on a short timescale, and discuss aspects of the protocol that hinder the formation of fumarate or lead to irreproducible results. We also provide experimental procedures and recommendations for performing reproducible kinetics experiments in which hydrogen gas is repeatedly bubbled into an aqueous solution, overcoming challenges related to the viscosity and surface tension of the water.
| Item Type: | Article |
|---|---|
| Erschienen: | 2021 |
| Creators: | Wienands, Laura ; Theiß, Franziska ; Eills, James ; Rösler, Lorenz ; Knecht, Stephan ; Buntkowsky, Gerd |
| Type of entry: | Bibliographie |
| Title: | Optimizing the Reaction Conditions for the Formation of Fumarate via Trans-Hydrogenation |
| Language: | English |
| Date: | 2021 |
| Place of Publication: | Darmstadt |
| Publisher: | Springer Nature |
| Journal or Publication Title: | Applied Magnetic Resonance |
| Volume of the journal: | 53 |
| Issue Number: | 3 |
| DOI: | 10.1007/s00723-021-01371-w |
| Corresponding Links: | |
| Abstract: | Parahydrogen-induced polarization is a hyperpolarization method for enhancing nuclear magnetic resonance signals by chemical reactions/interactions involving the para spin isomer of hydrogen gas. This method has allowed for biomolecules to be hyperpolarized to such a level that they can be used for real time in vivo metabolic imaging. One particularly promising example is fumarate, which can be rapidly and efficiently hyperpolarized at low cost by hydrogenating an acetylene dicarboxylate precursor molecule using parahydrogen. The reaction is relatively slow compared to the timescale on which the hyperpolarization relaxes back to thermal equilibrium, and an undesirable 2nd hydrogenation step can convert the fumarate into succinate. To date, the hydrogenation chemistry has not been thoroughly investigated, so previous work has been inconsistent in the chosen reaction conditions in the search for ever-higher reaction rate and yield. In this work we investigate the solution preparation protocols and the reaction conditions on the rate and yield of fumarate formation. We report conditions to reproducibly yield over 100 mM fumarate on a short timescale, and discuss aspects of the protocol that hinder the formation of fumarate or lead to irreproducible results. We also provide experimental procedures and recommendations for performing reproducible kinetics experiments in which hydrogen gas is repeatedly bubbled into an aqueous solution, overcoming challenges related to the viscosity and surface tension of the water. |
| Classification DDC: | 500 Science and mathematics > 530 Physics 500 Science and mathematics > 540 Chemistry |
| Divisions: | 07 Department of Chemistry 07 Department of Chemistry > Eduard Zintl-Institut 07 Department of Chemistry > Eduard Zintl-Institut > Physical Chemistry |
| Date Deposited: | 02 Aug 2024 12:54 |
| Last Modified: | 02 Aug 2024 12:54 |
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| Suche nach Titel in: | TUfind oder in Google |
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Optimizing the Reaction Conditions for the Formation of Fumarate via Trans-Hydrogenation. (deposited 13 Jul 2023 12:45)
- Optimizing the Reaction Conditions for the Formation of Fumarate via Trans-Hydrogenation. (deposited 02 Aug 2024 12:54) [Currently Displayed]
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