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

Trantzschel, T. and Bernarding, J. and Plaumann, M. and Lego, D. and Gutmann, T. and Ratajczyk, T. and Dillenberger, S. and Buntkowsky, G. and Bargon, J. and Bommerich, U. (2012):
Parahydrogen induced polarization in face of keto-enol tautomerism: proof of concept with hyperpolarized ethanol.
In: Physical Chemistry Chemical Physics, pp. 5601-5604, 14, (16), [Online-Edition: http://apps.webofknowledge.com/full_record.do?product=WOS&se...],
[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. and Bernarding, J. and Plaumann, M. and Lego, D. and Gutmann, T. and Ratajczyk, T. and Dillenberger, S. and Buntkowsky, G. and Bargon, J. and 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
Volume: 14
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
Official URL: http://apps.webofknowledge.com/full_record.do?product=WOS&se...
Additional Information:

915XZ Times Cited:9 Cited References Count:40

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