Trantzschel, T. ; Bernarding, J. ; Plaumann, M. ; Lego, D. ; Gutmann, T. ; Ratajczyk, T. ; Dillenberger, S. ; Buntkowsky, G. ; Bargon, J. ; Bommerich, U. (2012):
Parahydrogen induced polarization in face of keto-enol tautomerism: proof of concept with hyperpolarized ethanol.
In: Physical Chemistry Chemical Physics, 14 (16), pp. 5601-5604. [Article]
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.
Item Type: | Article |
---|---|
Erschienen: | 2012 |
Creators: | Trantzschel, T. ; Bernarding, J. ; Plaumann, M. ; Lego, D. ; Gutmann, T. ; Ratajczyk, T. ; Dillenberger, S. ; Buntkowsky, G. ; Bargon, J. ; Bommerich, U. |
Title: | Parahydrogen induced polarization in face of keto-enol tautomerism: proof of concept with hyperpolarized ethanol |
Language: | English |
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. |
Journal or Publication Title: | Physical Chemistry Chemical Physics |
Journal Volume: | 14 |
Issue Number: | 16 |
Uncontrolled Keywords: | hydrogen-induced polarization pasadena hyperpolarization magnetic-resonance c-13 order spectroscopy generation molecules alignment kinetics |
Divisions: | 07 Department of Chemistry 07 Department of Chemistry > Physical Chemistry |
Date Deposited: | 27 Oct 2014 20:51 |
URL / URN: | http://apps.webofknowledge.com/full_record.do?product=WOS&se... |
Additional Information: | 915XZ Times Cited:9 Cited References Count:40 |
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