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Application of Parahydrogen-Induced Polarization to Unprotected Dehydroamino Carboxylic Acids

Trantzschel, T. and Plaumann, M. and Bernarding, J. and Lego, D. and Ratajczyk, T. and Dillenberger, S. and Buntkowsky, G. and Bargon, J. and Bommerich, U. (2013):
Application of Parahydrogen-Induced Polarization to Unprotected Dehydroamino Carboxylic Acids.
44, In: Applied Magnetic Resonance, (1-2), pp. 267-278, [Online-Edition: http://apps.webofknowledge.com/full_record.do?product=WOS&se...],
[Article]

Abstract

One focus of current nuclear magnetic resonance (NMR) and magnetic resonance imaging (MRI) investigation is the hyperpolarization of biologically relevant substrates. In this study, the application of parahydrogen-induced polarization (PHIP) to amino carboxylic acids was enabled by protonation of the amino group as well as of the carboxylic acid. Due to the donor character of these functional groups, they usually act as ligands at the active catalytic sites. To enable parahydrogenation, blocking of the catalytic sites by the functional groups has to be avoided. In a new approach, this was realized via protonation of the starting material. For the first time PHIP spectra of allylglycine, vigabatrin and gamma-amino-butyric acid (GABA) were generated. The feasibility of the hydrogenation of amino carboxylic acids without using a protection group supersedes the deprotection reaction usually required. Hence, hydrogenation after protonation of the substrate opens the class of free dehydroamino carboxylic acids to PHIP.

Item Type: Article
Erschienen: 2013
Creators: Trantzschel, T. and Plaumann, M. and Bernarding, J. and Lego, D. and Ratajczyk, T. and Dillenberger, S. and Buntkowsky, G. and Bargon, J. and Bommerich, U.
Title: Application of Parahydrogen-Induced Polarization to Unprotected Dehydroamino Carboxylic Acids
Language: English
Abstract:

One focus of current nuclear magnetic resonance (NMR) and magnetic resonance imaging (MRI) investigation is the hyperpolarization of biologically relevant substrates. In this study, the application of parahydrogen-induced polarization (PHIP) to amino carboxylic acids was enabled by protonation of the amino group as well as of the carboxylic acid. Due to the donor character of these functional groups, they usually act as ligands at the active catalytic sites. To enable parahydrogenation, blocking of the catalytic sites by the functional groups has to be avoided. In a new approach, this was realized via protonation of the starting material. For the first time PHIP spectra of allylglycine, vigabatrin and gamma-amino-butyric acid (GABA) were generated. The feasibility of the hydrogenation of amino carboxylic acids without using a protection group supersedes the deprotection reaction usually required. Hence, hydrogenation after protonation of the substrate opens the class of free dehydroamino carboxylic acids to PHIP.

Journal or Publication Title: Applied Magnetic Resonance
Volume: 44
Number: 1-2
Uncontrolled Keywords: hydrogen-induced polarization nuclear-magnetic-resonance pasadena hyperpolarization homogeneous hydrogenation c-13 order field spectroscopy molecules alignment
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:

074EU Times Cited:4 Cited References Count:45

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