Synlett 2020; 31(07): 718-722
DOI: 10.1055/s-0039-1691584
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Phosphatidylcholines Possessing Functionalized Acids at sn-2, and 13C–14N and 13C–31P Couplings in Their 13C NMR Spectra

Masao Morita
a  Department of Bioengineering, Tokyo Institute of Technology, Box B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan   Email: ykobayas@bio.titech.ac.jp
,
Shun Saito
a  Department of Bioengineering, Tokyo Institute of Technology, Box B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan   Email: ykobayas@bio.titech.ac.jp
,
Riku Shinohara
a  Department of Bioengineering, Tokyo Institute of Technology, Box B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan   Email: ykobayas@bio.titech.ac.jp
,
Ryohei Aoyagi
b  Division of Physiological Chemistry and Metabolism, Graduate School of Pharmaceutical Sciences, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan
c  Laboratory for Metabolomics, RIKEN Center for Integrative Medical Sciences, 1-7-22, Suehiro-cho, Tsurumi-ku, Yokohama 230-0045, Japan
,
Makoto Arita
b  Division of Physiological Chemistry and Metabolism, Graduate School of Pharmaceutical Sciences, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan
c  Laboratory for Metabolomics, RIKEN Center for Integrative Medical Sciences, 1-7-22, Suehiro-cho, Tsurumi-ku, Yokohama 230-0045, Japan
d  Cellular and Molecular Epigenetics Laboratory, Graduate School of Medical Life Science, Yokohama City University, 1-7-29, Suehiro-cho, Tsurumi-ku, Yokohama 230-0045, Japan
,
Yuichi Kobayashi
a  Department of Bioengineering, Tokyo Institute of Technology, Box B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan   Email: ykobayas@bio.titech.ac.jp
› Author Affiliations
This work was supported in part by the Japan Society for the Promotion of Science (JSPS KAKENHI, Grant No. JP15H05904 (Y.K.), JP15H05897 (M.A.), and JP15H05898 (M.A.).
Further Information

Publication History

Received: 04 November 2019

Accepted after revision: 08 January 2020

Publication Date:
28 January 2020 (online)


Abstract

Although 4-Me2NC5H4N (DMAP) is a standard base for esterification of (2-Me-6-NO2-C6H3CO)2O (MNBA), N-methylimidazole (NMI) was examined for the condensation of acids with 1-stearoyl-lysophosphatidylcholine because of the non-tailing nature of NMI on silica gel. Acids tested were EPA, α-linolenic acid, TBS ethers of 18-HEPE and ricinoleic acid, acid-labile epoxy acids, and a phenyldiynyl acid. The condensation proceeded well with these acids, and chromatographic separation of resulting phosphatidylcholines and remaining NMI was easily performed. During the characterization of the products by 13C NMR spectroscopy, 13C–14N and 13C–31P couplings were observed.

Supporting Information

 
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