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The structure of the core polyol of the ether lipids from Sulfolobus acidocaldarius
Author(s) -
Sugai Akihiko,
Sakuma Rie,
Fukuda Ikuko,
Kurosawa Norio,
Itoh Yuko H.,
Kon Kazuo,
Ando Susumu,
Itoh Toshihiro
Publication year - 1995
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02536042
Subject(s) - sulfolobus acidocaldarius , polyol , ether , chemistry , hydroxymethyl , molecule , glycerol , stereochemistry , nuclear magnetic resonance spectroscopy , chemical structure , organic chemistry , biochemistry , polyurethane , archaea , gene
Abstract The major ether‐type lipid structures of Sulfolobus 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 BCl 3 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 in Sulfolobales .