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

Masao Morita, Shun Saito, Riku Shinohara, Ryohei Aoyagi, Makoto Arita, Yuichi Kobayashi

Research output: Contribution to journalArticle

Abstract

Although 4-Me 2 NC 5 H 4 N (DMAP) is a standard base for esterification of (2-Me-6-NO 2 -C 6 H 3 CO) 2 O (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 13 C NMR spectroscopy, 13 C- 14 N and 13 C- 31 P couplings were observed.

Original languageEnglish
Pages (from-to)718-722
Number of pages5
JournalSynlett
Volume31
Issue number7
DOIs
Publication statusPublished - 2020 Apr 22

Keywords

  • C- N coupling
  • N -methylimidazole
  • Shiina reagent
  • functionalized acid
  • lyso-phosphatidylcholine
  • synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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