Phosphatidylcholine bearing 6,6-dideuterated oleic acid: A useful solid-state 2H NMR probe for investigating membrane properties

Jin Cui; Sébastien Lethu; Tomokazu Yasuda; Shigeru Matsuoka; Nobuaki Matsumori; Fuminori Sato; Michio Murata

doi:10.1016/j.bmcl.2014.11.072

Phosphatidylcholine bearing 6,6-dideuterated oleic acid: A useful solid-state ²H NMR probe for investigating membrane properties

Jin Cui, Sébastien Lethu, Tomokazu Yasuda, Shigeru Matsuoka, Nobuaki Matsumori, Fuminori Sato, Michio Murata

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

Lipid organization has been at the center of research on lipid rafts. Dioleoylphosphatidylcholine (DOPC) is a typical unsaturated lipid. Very few studies have reported its thermodynamics in raft-like membranes. Herein, we have developed a highly efficient synthetic method for [C6-²H₂] oleic acid, and newly synthesized [C6-²H₂] DOPC. In raft-like oriented bilayers, [C6-²H₂] DOPC shows clear phase separation and characteristic phase behavior at various temperature. It has been successfully utilized for the comparison of membrane properties between sphingomyelin (SM) and dihydrosphingomyelin (DHSM) membranes.

Original language	English
Pages (from-to)	203-206
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	25
Issue number	2
DOIs	https://doi.org/10.1016/j.bmcl.2014.11.072
Publication status	Published - Jan 15 2015
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2014.11.072

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title = "Phosphatidylcholine bearing 6,6-dideuterated oleic acid: A useful solid-state 2H NMR probe for investigating membrane properties",

abstract = "Lipid organization has been at the center of research on lipid rafts. Dioleoylphosphatidylcholine (DOPC) is a typical unsaturated lipid. Very few studies have reported its thermodynamics in raft-like membranes. Herein, we have developed a highly efficient synthetic method for [C6-2H2] oleic acid, and newly synthesized [C6-2H2] DOPC. In raft-like oriented bilayers, [C6-2H2] DOPC shows clear phase separation and characteristic phase behavior at various temperature. It has been successfully utilized for the comparison of membrane properties between sphingomyelin (SM) and dihydrosphingomyelin (DHSM) membranes.",

author = "Jin Cui and S{\'e}bastien Lethu and Tomokazu Yasuda and Shigeru Matsuoka and Nobuaki Matsumori and Fuminori Sato and Michio Murata",

note = "Funding Information: We thank Dr. Yuichi Umegawa for the kind support for 2 H NMR measurements. This work was supported by Japanese Society of Technology (JST) ERATO , Lipid Active Structure Project, and partly by Grant-In-Aids for Scientific Research (A) (No. 25242073 ). Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",

year = "2015",

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doi = "10.1016/j.bmcl.2014.11.072",

language = "English",

volume = "25",

pages = "203--206",

journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Phosphatidylcholine bearing 6,6-dideuterated oleic acid

T2 - A useful solid-state 2H NMR probe for investigating membrane properties

AU - Cui, Jin

AU - Lethu, Sébastien

AU - Yasuda, Tomokazu

AU - Matsuoka, Shigeru

AU - Matsumori, Nobuaki

AU - Sato, Fuminori

AU - Murata, Michio

N1 - Funding Information: We thank Dr. Yuichi Umegawa for the kind support for 2 H NMR measurements. This work was supported by Japanese Society of Technology (JST) ERATO , Lipid Active Structure Project, and partly by Grant-In-Aids for Scientific Research (A) (No. 25242073 ). Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

PY - 2015/1/15

Y1 - 2015/1/15

N2 - Lipid organization has been at the center of research on lipid rafts. Dioleoylphosphatidylcholine (DOPC) is a typical unsaturated lipid. Very few studies have reported its thermodynamics in raft-like membranes. Herein, we have developed a highly efficient synthetic method for [C6-2H2] oleic acid, and newly synthesized [C6-2H2] DOPC. In raft-like oriented bilayers, [C6-2H2] DOPC shows clear phase separation and characteristic phase behavior at various temperature. It has been successfully utilized for the comparison of membrane properties between sphingomyelin (SM) and dihydrosphingomyelin (DHSM) membranes.

AB - Lipid organization has been at the center of research on lipid rafts. Dioleoylphosphatidylcholine (DOPC) is a typical unsaturated lipid. Very few studies have reported its thermodynamics in raft-like membranes. Herein, we have developed a highly efficient synthetic method for [C6-2H2] oleic acid, and newly synthesized [C6-2H2] DOPC. In raft-like oriented bilayers, [C6-2H2] DOPC shows clear phase separation and characteristic phase behavior at various temperature. It has been successfully utilized for the comparison of membrane properties between sphingomyelin (SM) and dihydrosphingomyelin (DHSM) membranes.

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JO - Bioorganic and Medicinal Chemistry Letters

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ER -

Phosphatidylcholine bearing 6,6-dideuterated oleic acid: A useful solid-state ²H NMR probe for investigating membrane properties

Abstract

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