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

Gowda, Siddabasave Gowda B.; Fuda, Hirotoshi; Yamamoto, Yusuke; Chiba, Hitoshi; Hui, Shu-Ping

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

Gowda, Siddabasave Gowda B.; Fuda, Hirotoshi; Yamamoto, Yusuke et al.

Lipids, 2020, 55(4), 395-401

Permalink : https://hdl.handle.net/2115/82109

このアイテムのアクセス数:606件（2026-10-14 19:44 集計）

閲覧可能ファイル

ファイル	フォーマット	サイズ	閲覧回数	説明
Manuscript_LIPIDS-20-0006	pdf	672 KB	496

論文情報

ファイル出力 EndNote Basic出力 Mendeley出力

アクセス権	open access
URI	https://hdl.handle.net/2115/82109
タイトル	A Simple and Efficient Method for Synthesis of sn-Glycero-Phosphoethanolamine
著者	Gowda, Siddabasave Gowda B. ; Fuda, Hirotoshi ; Yamamoto, Yusuke ; Chiba, Hitoshi ; Hui, Shu-Ping
著者名 Gowda, Siddabasave Gowda B.
e-Rad_Researcher 60576172 著者名 Fuda, Hirotoshi
著者名 Yamamoto, Yusuke
e-Rad_Researcher 70197622 著者名 Chiba, Hitoshi
e-Rad_Researcher 90337030 著者名 Hui, Shu-Ping
言語	英語
キーワード	Acid hydrolysis
	Glycerophospholipids
	High-resolution mass spectrometry
	Nuclear-magnetic resonance
	sn-glycero-phosphoethanolamine
	Trityl deprotection
発行日	2020-07
出版者	John Wiley & Sons
収録物名	Lipids
巻(号)	55(4)
ページ	395-401
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
権利情報	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.
PISSN	0024-4201
EISSN	1558-9307
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1002/lipd.12243