25-30 August 2019
Henry Ford Building
Europe/Berlin timezone

A PHIP Strategy Yielding 13C-Hyperpolarized Unprotected Amino Acids in Aqueous Solutions

Not scheduled
4h
Harnack House and Henry Ford Building

Harnack House and Henry Ford Building

Board: 214
Poster Posters

Speaker

Dr Lukas Kaltschnee (Max-Planck-Institute for Biophysical Chemistry and Center for Biostructural Imaging of Neurodegeneration)

Description

The hyperpolarization of biologically relevant molecules for signal-enhanced magnetic resonance detection holds great promise for studying biological processes in vitro and in vivo. Being important metabolites as well as the building blocks of peptides, the canonical amino acids are promising targets for hyperpolarization, and a number of parahydrogen based strategies have been devised to hyperpolarize amino acids[1-7]. For biochemical and biomedical applications, however, these approaches suffer from limited biocompatibility of the obtained products, due to the utilization of toxic solvents, such as methanol-d4, or because chemically modified (e.g. N-protected) amino acids are obtained.
Herein we present a PHIP strategy for hyperpolarizing proteinogenic amino acids under conditions of improved biocompatibility. We obtain chemically unmodified proteinogenic amino acids, which are directly produced in aqueous media. This is enabled through the use of a heterogeneous nanocatalyst[7], which allows for PHIP hyperpolarization of the N-unprotected amino acids in water and further provides the prospect of easy catalyst separation. Efficient coherent hyperpolarization transfer from 1H to 13C is achieved at high field, using the recently presented ESOTHERIC[8] approach. This allows for polarization storage on the carbonyl-13C for tens of seconds.
Whereas the strategy presented is demonstrated here for the hyperpolarization of single amino acids, it is likely that the approach can be extended into a general strategy for 13C-hyperpolarizing small synthetic peptides in aqueous solutions.

[1] Glöggler et al., Phys. Chem. Chem. Phys. 2011, 13, 13759.
[2] Trantzschel et al., Appl. Magn. Reson. 2013, 44, 267.
[3] Körner et al., Chem. Commun. 2013, 49, 7839.
[4] Soon et al., Chem. Commun. 2013, 49, 5304.
[5] Sauer et al., Angew. Chem. Int. Ed. 2014, 53, 12941.
[6] Glöggler, Wagner, Bouchard, Chem. Sci. 2015, 6, 4261.
[7] McCormick et al., Angew. Chem. Int. Ed. 2018, 57, 10696.
[8] Korchak et al., ChemistryOpen 2018, 7, 344.

Primary authors

Dr Lukas Kaltschnee (Max-Planck-Institute for Biophysical Chemistry and Center for Biostructural Imaging of Neurodegeneration) Dr Anil P. Jagtap (Max-Planck-Institute for Biophysical Chemistry and Center for Biostructural Imaging of Neurodegeneration) Dr Jeffrey McCormick (Department of Chemistry and Biochemistry, University of California Los Angeles) Dr Shawn Wagner (Biomedical Imaging Research Institute, Cedars Sinai Medical Center, Los Angeles) Prof. Louis-S. Bouchard (Department of Chemistry and Biochemistry, University of California Los Angeles) Prof. Marcel Utz (School of Chemistry, University of Southampton) Prof. Christian Griesinger (Max-Planck-Institute for Biophysical Chemistry) Dr Stefan Glöggler (Max-Planck-Institute for Biophysical Chemistry and Center for Biostructural Imaging of Neurodegeneration)

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