Work

Efficient Synthesis of Molecular Precursors for Para‐Hydrogen‐Induced Polarization of Ethyl Acetate‐1‐13C and Beyond

Year: 2016

Type: article

Abstract: A scalable and versatile methodology for production of vinylated carboxylic compounds with (13) C isotopic label in C1 position is described. It allowed synthesis of vinyl acetate-1-(13) C, which is a precursor for preparation of (13) C hyperpolarized ethyl acetate-1-(13) C, which provides a convenient vehicle for potential in vivo delivery of hyperpolarized acetate to probe metabolism in living organisms. Kinetics of vinyl acetate molecular hydrogenation and polarization transfer from para-hydrogen to (13) C via magnetic field cycling were investigated. Nascent proton nuclear spin polarization (%PH ) of ca. 3.3 % and carbon-13 polarization (%P13C ) of ca. 1.8 % were achieved in ethyl acetate utilizing 50 % para-hydrogen corresponding to ca. 50 % polarization transfer efficiency. The use of nearly 100% para-hydrogen and the improvements of %PH of para-hydrogen-nascent protons may enable production of (13) C hyperpolarized contrast agents with %P13C of 20-50 % in seconds using this chemistry.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201600521

Authors: Roman V. Shchepin, Danila A. Barskiy, Aaron M. Coffey, Isaac V. Manzanera Esteve, Eduard Y. Chekmenev

Institutions: Vanderbilt University, Vanderbilt-Ingram Cancer Center, Russian Academy of Sciences

Language: English

Topic: Advanced NMR Techniques and Applications

Subfield: Spectroscopy

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institutes of Health, National Institute of Biomedical Imaging and Bioengineering

Awards: G1815062656, G196227769, International Collaboration in Chemistry: Collaborative Research: Development of Novel Catalysts and Approaches for Parahydrogen-Induced Enhancement of Magnetic Resonance, G4955926212