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A Simple and Efficient Method for Synthesis of sn-Glycero-Phosphoethanolamine
| Title: | A Simple and Efficient Method for Synthesis of sn-Glycero-Phosphoethanolamine |
| Authors: | Gowda, Siddabasave Gowda B. Browse this author | | Fuda, Hirotoshi Browse this author →KAKEN DB | | Yamamoto, Yusuke Browse this author | | Chiba, Hitoshi Browse this author →KAKEN DB | | Hui, Shu-Ping Browse this author →KAKEN DB |
| Keywords: | Acid hydrolysis | | Glycerophospholipids | | High-resolution mass spectrometry | | Nuclear-magnetic resonance | | sn-glycero-phosphoethanolamine | | Trityl deprotection |
| Issue Date: | Jul-2020 |
| Publisher: | John Wiley & Sons |
| Journal Title: | Lipids |
| Volume: | 55 |
| Issue: | 4 |
| Start Page: | 395 |
| End Page: | 401 |
| Publisher 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. |
| Rights: | This 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. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/82109 |
| Appears in Collections: | 保健科学院・保健科学研究院 (Graduate School of Health Sciences / Faculty of Health Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 惠 淑萍
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