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- Title
Efficient Synthesis of Molecular Precursors for Para-Hydrogen-Induced Polarization of Ethyl Acetate-1-<sup>13</sup>C and Beyond.
- Authors
Shchepin, Roman V.; Barskiy, Danila A.; Coffey, Aaron M.; Manzanera Esteve, Isaac V.; Chekmenev , Eduard Y.
- Abstract
A scalable and versatile methodology for production of vinylated carboxylic compounds with 13C isotopic label in C1 position is described. It allowed synthesis of vinyl acetate-1-13C, which is a precursor for preparation of 13C hyperpolarized ethyl acetate-1-13C, 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 13C 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 13C hyperpolarized contrast agents with % P13C of 20-50 % in seconds using this chemistry.
- Subjects
CHEMICAL synthesis; CHEMICAL precursors; HYDROGEN; POLARIZATION (Nuclear physics); ACETATES; PROTONS
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 20, p6071
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201600521