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

详细信息    查看全文

• 作者：Prof. Roman V. Shchepin ; Dr. Danila A. Barskiy ; Dr. Aaron M. Coffey ; Dr. Isaac V. Manzanera Esteve and Prof. Eduard Y. Chekmenev
• 刊名：Angewandte Chemie
• 出版年：2016
• 出版时间：May 10, 2016
• 年：2016
• 卷：128
• 期：20
• 页码：6175-6178
• 全文大小：1022K
• ISSN：1521-3757

文摘

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 (%P_H) of ca. 3.3 % and carbon-13 polarization (%P_13C) 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 %P_H of para-hydrogen-nascent protons may enable production of ¹³C hyperpolarized contrast agents with %P_13C of 20–50 % in seconds using this chemistry.