Parahydrogen induced polarization in face of keto–enol tautomerism: proof of concept with hyperpolarized ethanol

Literature Information

Publication Date 2012-02-28
DOI 10.1039/C2CP40272F
Impact Factor 3.676
Authors

Thomas Trantzschel, Johannes Bernarding, Markus Plaumann, Denise Lego, Torsten Gutmann, Tomasz Ratajczyk, Sonja Dillenberger, Gerd Buntkowsky, Joachim Bargon, Ute Bommerich


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Abstract

Hyperpolarization (HP) techniques are increasingly important in magnetic resonance imaging (MRI) and spectroscopy (MRS). HP methods have the potential to overcome the fundamentally low sensitivity of magnetic resonance (MR). A breakthrough of HP-MR in life sciences and medical applications is still limited by the small number of accessible, physiologically relevant substrates. Our study presents a new approach to extend PHIP to substrates that primarily cannot be hyperpolarized due to a steady intramolecular re-arrangement, the so-called keto–enol tautomerism. To overcome this obstacle we exploited the fact that instead of the instable enol form the corresponding stable ester can be used as a precursor molecule. This strategy now enables the hydrogenation which is required to apply the standard PHIP procedure. As the final step a hydrolysis is necessary to release the hyperpolarized target molecule. Using this new approach ethanol was successfully hyperpolarized for the first time. It may therefore be assumed that the outlined multi-step procedure can be used for other keto–enol tautomerized substances thereby opening the application of PHIP to a multitude of molecules relevant to analyzing metabolic pathways.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
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