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

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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
High-resolution mass spectrometry
Nuclear-magnetic resonance
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 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)
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)

Submitter: 惠 淑萍

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