2024-03-28T08:11:25Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/821092022-11-17T02:08:08Zhdl_2115_35410hdl_2115_35409A Simple and Efficient Method for Synthesis of sn-Glycero-PhosphoethanolamineGowda, Siddabasave Gowda B.1000060576172Fuda, HirotoshiYamamoto, Yusuke1000070197622Chiba, Hitoshi1000090337030Hui, Shu-Pingopen accessThis is the peer reviewed version of the following article: B. Gowda, S.G., Fuda, H., Yamamoto, Y., Chiba, H. and Hui, S.‐P. (2020), A Simple and Efficient Method for Synthesis of sn ‐Glycero ‐Phosphoethanolamine. Lipids, which has been published in final form at https://doi.org/10.1002/lipd.12243. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.Acid hydrolysisGlycerophospholipidsHigh-resolution mass spectrometryNuclear-magnetic resonancesn-glycero-phosphoethanolamineTrityl deprotection490An 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.John Wiley & Sons2020-07engjournal articleAMhttp://hdl.handle.net/2115/82109https://doi.org/10.1002/lipd.122430024-42011558-9307Lipids554395401https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/82109/1/Manuscript_LIPIDS-20-0006.pdfapplication/pdf672.66 KB2020-07