The structure of the core polyol of the ether lipids from Sulfolobus acidocaldarius.
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-cyclopentanetet raol 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 degrees C for 60 h, producing 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.
Sugai
A
A
Division of Chemistry, College of Liberal Arts and Sciences, Kitasato University, Kanagawa, Japan.
Sakuma
R
R
Fukuda
I
I
Kurosawa
N
N
Itoh
Y H
YH
Kon
K
K
Ando
S
S
Itoh
T
T
D000107:Acetylation; D004075:Diglycerides / Q000737:chemistry*; D004987:Ethers; D005995:Glyceryl Ethers / Q000737:chemistry*; D006017:Glycolipids / Q000737:chemistry*; D008055:Lipids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D016944:Sulfolobus / Q000737:chemistry*
D004075:Diglycerides; D004987:Ethers; D005995:Glyceryl Ethers; D006017:Glycolipids; D008055:Lipids; C094418:caldarchaeol; C094613:calditoglycerocaldarchaeol