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Synthesis of (2 beta,3 alpha,6-H-2(3))cholesteryl linoleate and cholesteryl oleate as internal standards for mass spectrometry

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Title: Synthesis of (2 beta,3 alpha,6-H-2(3))cholesteryl linoleate and cholesteryl oleate as internal standards for mass spectrometry
Authors: Miura, Yusuke Browse this author
Hui, Shu-Ping Browse this author →KAKEN DB
Shrestha, Rojeet Browse this author
Hiruma, Takahisa Browse this author
Takeda, Seiji Browse this author →KAKEN DB
Fuda, Hirotoshi Browse this author
Ikegawa, Shigeo Browse this author
Hirano, Ken-ichi Browse this author
Chiba, Hitoshi Browse this author →KAKEN DB
Keywords: Multiple deuteration
Trans-diaxial opening
Sodium borodeuteride
Liquid chromatography/mass spectrometry
Cholesterol
Cholesteryl ester
Issue Date: Mar-2016
Publisher: Elsevier
Journal Title: Steroids
Volume: 107
Start Page: 1
End Page: 9
Publisher DOI: 10.1016/j.steroids.2015.12.004
PMID: 26703443
Abstract: The accurate analysis of trace component in complex biological matrices requires the use of reliable standards. For liquid chromatography/mass spectrometry analysis, the stable isotope-labeled derivatives of the analyte molecules are the most appropriate internal standards. We report here the synthesis of (2 beta,3 alpha,6-H-2(3))cholesteryl linoleate and oleate containing three non-exchangeable deuterium in the steroid ring. The principal reactions used were: (1) trans diaxial opening of 2 alpha,3 alpha-epoxy-6-oxo-5 alpha-cholestane with LiAlD4 and subsequent oxidation of the resulting (2 beta,6 alpha-H-2(2))-3 alpha,6 beta-diol with Jones' reagent, followed by reduction of the resulting (2 beta-H-2)-3,6-dione with NaBD4 leading to the (2 beta,3 alpha,6 alpha-H-2(3))-3 beta,6 beta-dihydroxy-5 alpha-cholestane, (2) selective protection of the 3 beta-hydroxy group as the tert-butyldimethylsilyl ether, (3) dehydration of the 6 beta-hydroxy group with POCI3 and removal of tert-butyldimethylsilyloxy groups with 5 M HCl in acetone, and (4) esterification of the resultant (2 beta,3 alpha,6-H-2(3))cholesterol with linoleic and oleic acids using 1-(3-dimethylaminopropyI)-3-ethylcarbodiim ide. The isotopic purity was found to be satisfactory by mass spectrometry, and nuclear magnetic resonance properties of the new compounds were tabulated. The labeled compounds can be used as internal standards in liquid chromatography/mass spectrometry assays for clinical and biochemical studies. (C) 2015 Elsevier Inc. All rights reserved.
Rights: ©2016. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
http://creativecommons.org/licenses/by-nc-nd/4.0/
Type: article (author version)
URI: http://hdl.handle.net/2115/65010
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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