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The structure of the core polyol of the ether lipids fromSulfolobus acidocaldarius

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Lipids

Abstract

The major ether-type lipid structures ofSulfolobus acidocaldarius (ATCC33909) were composed of caldarchaeol and calditoglycerocaldarchaeol. However, the characterization by nuclear magnetic resonance spectroscopy and mass spectrometry showed that the structure of calditol in calditoglycerocaldarchaeol is not nonitol, 2-(1′,2′,3′-trihydroxypropyl)1,2,3,4,5,6-hexahydroxyhexane, but 2-hydroxymethyl-1-(2,3-dihydroxypropoxy),2,3,4,5-cyclopentanetetraol with an ether linkage in the molecule. Such an intermolecular ether linkage was resistant, to BCl3 treatment, but nonresistant to 57% HI degradation treatment conducted at 100°C for 60 h, producting 2-hydroxymethyl-1,2,3,4,5-cyclopentanepentaol from calditol as reaction product. Further, it was confirmed that the structure of calditol is essentially a derivative of glycerol, and hydrocarbon chains were conjugated to the glycerol-like site in the structure. The calditol with an ether linkage in the molecule suggested an important role regarding the properties of heat-resistance and acid-resistance observed inSulfolobales.

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Abbreviations

CI:

chemicals ionization

DEPT:

distortionless enhancement polarization transfer

DMSO:

dimethyl sulfoxide

FAB-MS:

fast atom bombardment mass spectrometry

GC/MS:

gas chromatography/mass spectrometry

HMBC:

1H-Detected multiple-bond connectivity

HPTLC:

high-performance thin-layer chromatography

NBA:

3-nitrobenzylalcohol

NMR:

nuclear magnetic resonance spectroscopy

NOE:

nuclear Overhauser effect

TLC:

thin-layer chromatography

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Authors and Affiliations

  1. Division of Chemistry, College of Liberal Arts and Sciences, Kitasato University, 1-15-1 Kitasato, Sagamihara, 228, Kanagawa, Japan

    Akihiko Sugai, Rie Sakuma, Ikuko Fukuda & Toshihiro Itoh

  2. Department of Bioengineering, Faculty of Engineering, Soka University, Hachioji, 192, Tokyo, Japan

    Norio Kurosawa & Yuko H. Itoh

  3. Department of Membrane Biochemistry, Tokyo Metropolitan Institute of Gerontology, Itabashi-ku, 173, Tokyo, Japan

    Kazuo Kon & Susumu Ando

Authors
  1. Akihiko Sugai
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  2. Rie Sakuma
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  3. Ikuko Fukuda
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  4. Norio Kurosawa
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  5. Yuko H. Itoh
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  6. Kazuo Kon
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  7. Susumu Ando
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  8. Toshihiro Itoh
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Sugai, A., Sakuma, R., Fukuda, I. et al. The structure of the core polyol of the ether lipids fromSulfolobus acidocaldarius . Lipids 30, 339–344 (1995). https://doi.org/10.1007/BF02536042

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  • DOI: https://doi.org/10.1007/BF02536042

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