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Nuclear magnetic resonance characterization of 6α-chloro-5β-cholestane-3β,5-diol formed from the reaction of hypochlorous acid with cholesterol

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Lipids

Abstract

Hyopochlorous acid generated by neutrophil myeloperoxidase has been shown to convert cholesterol into three different chlorohydrin isomers which previously had not been fully characterized. We have reacted hypochlorous acid with cholesterol/1,2-dipalmitoyl phosphatidylcholine liposomes to give these three major products and established that they are 6β-chloro-5α-cholestane-3β,5-diol (chlorohydrin 1), 5α-chloro-6β-cholestane-3β,6-diol (chlorohydrin 2) and 6α-chloro-5β-cholestane-3β,5-diol (chlorohydrin 3). These products were separated by thin-layer chromatography and fully characterized by 1H, 13C, attached proton test, doublequantum correlation spectroscopy, total correlation spectroscopy, heteronuclear multiple bond correlation and heteronuclear multiple quantum coherence nuclear magnetic resonance spectroscopy.

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Abbreviations

APT:

attached proton test

DPPC:

1,2-dipalmitoyl phosphatidylcholine

DQCOSY:

doublequantum correlation spectroscopy

GC-MS:

gas chromatography-mass spectrometry

HMBC:

heteronuclear multiple bond correlation spectroscopy

HMQC:

heteronuclear multiple quantum coherence spectroscopy

NMR:

nuclear magnetic resonance

PBS:

phosphate-buffered saline

TLC:

thin-layer chromatography

TOCSY:

total correlation spectroscopy

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Authors and Affiliations

  1. Department of Chemistry, University of Canterbury, Christchurch, New Zealand

    John W. Blunt, Andrew J. Phillips & Andrew D. Abell

  2. Department of Pathology, Christchurch School of Medicine, P.O. Box 4345, Christchurch, New Zealand

    Anitra C. Carr & Christine C. Winterbourn

Authors
  1. Anitra C. Carr
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  2. Christine C. Winterbourn
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  3. John W. Blunt
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  4. Andrew J. Phillips
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  5. Andrew D. Abell
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Carr, A.C., Winterbourn, C.C., Blunt, J.W. et al. Nuclear magnetic resonance characterization of 6α-chloro-5β-cholestane-3β,5-diol formed from the reaction of hypochlorous acid with cholesterol. Lipids 32, 363–367 (1997). https://doi.org/10.1007/s11745-997-0046-8

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  • DOI: https://doi.org/10.1007/s11745-997-0046-8

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