A Simple and Efficient Method for Synthesis of sn-Glycero-Phosphoethanolamine

  • Lipids. 2020 Jul;55(4):395-401. doi: 10.1002/lipd.12243.
Siddabasave Gowda B Gowda  1 ,  Hirotoshi Fuda  1 ,  Yusuke Yamamoto  2 ,  Hitoshi Chiba  3 ,  Shu-Ping Hui  1
Affiliations
  • 1. Faculty of Health Sciences, Hokkaido University, Kita-12, Nishi-5, Kita-ku, Sapporo, 060-0812, Japan.
  • 2. Graduate School of Health Sciences, Hokkaido University, Kita-12, Nishi-5, Kita-ku, Sapporo, 060-0812, Japan.
  • 3. Department of Nutrition, Sapporo University of Health Sciences, Nakanuma, Nishi 4-2-1-15, Higashi-ku, Sapporo, 007-0894, Japan.
PMID: 32406068 DOI: 10.1002/lipd.12243
Abstract

An efficient three-step strategy for the convenient synthesis of Sn-glycero-3-phosphoethanolamine (GroPEtn) from a commercially available 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE) is reported. Direct hydrolysis of DPPE produces a complex inseparable mixture, hence a protection and deprotection strategy is employed to prepare GroPEtn. The primary amine of DPPE is protected with a highly stable acid-labile trityl group, followed by strong base hydrolysis of N-trityl-DPPE gives N-trityl-GroPEtn. Further a mild, rapid, and efficient deprotection method is established using trifluoroacetic acid to remove N-trityl moiety, affords GroPEtn as a single product. This is the first semisynthetic approach and efficient method to produce GroPEtn with a total yield of 66% in three steps. GroPEtn did not show any cytotoxicity against human kidney (HK-2) cells and reporter gene assay for activation of Keap1-Nrf2-mediated antioxidant defense mechanism showed no significant effects.

Keywords
Acid hydrolysis; Glycerophospholipids; High-resolution mass spectrometry; Nuclear-magnetic resonance; Trityl deprotection; sn-glycero-phosphoethanolamine.
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