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Simple chemical syntheses of TAG monohydroperoxides

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Lipids

Abstract

For the purpose of synthesizing standards to be used in the quantification of TAG hydroperoxides, three TAG (1,2-dioleoyl-3-palmitoylglycerol, 1-oleoyl-2-linoleoyl-3-palmitoylglycerol, and triolein) monohydroperoxides were chemically synthesized as authentic specimens. TAG were prepared by using a simple condensation in pyridine of glycerol and the corresponding acid chlorides. These TAG were then converted into monohydroperoxides by a photosensitized peroxidation. The synthesized monohydroperoxides were analyzed by normal-phase and RP-HPLC. The results of normal-phase HPLC analysis showed that monohydroperoxides from a corresponding TAG were a mixture of regioisomers. In RP-HPLC, however, the regioisomers of monohydroperoxides were not separated and gave a single peak, which may improve the sensitivity for the detection of TAG monohydroperoxides. In this study TAG monohydroperoxide standards were synthesized; these will be useful for the study of yet unknown biological and pathological roles of TAG hydroperoxides.

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Abbreviations

OLP:

1-oleoyl-2-linoleoyl-3-palmitoylglycerol

OOO:

triolein

OOP:

1,2-dioleoyl-3-palmitoylglycerol

POP:

2-oleoyl-1,3-dipalmitoylglycerol

PPO:

1-oleoyl-2,3-dipalmitoylglycerol

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, 061-0293, Hokkaido, Japan

    Shu-Ping Hui, Tsuyoshi Murai, Teruki Yoshimura & Takao Kurosawa

  2. Department of Laboratory Medicine, Hokkaido University School of Medicine, Kita-14, Nishi-5, 060-8648, Sapporo, Japan

    Hitoshi Chiba

Authors
  1. Shu-Ping Hui
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  2. Tsuyoshi Murai
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  3. Teruki Yoshimura
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  4. Hitoshi Chiba
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  5. Takao Kurosawa
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Correspondence to Takao Kurosawa.

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Hui, SP., Murai, T., Yoshimura, T. et al. Simple chemical syntheses of TAG monohydroperoxides. Lipids 38, 1287–1292 (2003). https://doi.org/10.1007/s11745-003-1191-9

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  • DOI: https://doi.org/10.1007/s11745-003-1191-9

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