2001
DOI: 10.1016/s0040-4039(01)00305-7
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A di- O -dihydrogeranylgeranyl glycerol from Thermococcus S 557, a novel ether lipid, and likely intermediate in the biosynthesis of diethers in Archæa

Abstract: The lipids of a deep-sea hydrothermal vent archaeon, Thermococcus S 557, were isolated, purified and structurally determined. Based on acid methanolysis and spectroscopic studies, the polar lipids were shown to comprise diphytanyl glycerol and dibiphytanyl diglycerol, typical membrane lipids of Archaea. From the neutral lipids, 2,3-di-O-dihydro-14,15-geranylgeranyl glycerol was isolated. This novel ether lipid is, very likely, a close intermediate in the biosynthesis of diphytanyl glycerol diether in Archaea.

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Cited by 27 publications
(17 citation statements)
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“…III). These results confirmed the presence of unsaturated archaeol, consistent with the previously studied structure of 2,3-di-O-dihydrogeranylgeranyl glycerol diether (31).…”
Section: Nmr Analysis Of Total Polar Lipidssupporting
confidence: 92%
“…III). These results confirmed the presence of unsaturated archaeol, consistent with the previously studied structure of 2,3-di-O-dihydrogeranylgeranyl glycerol diether (31).…”
Section: Nmr Analysis Of Total Polar Lipidssupporting
confidence: 92%
“…Unsaturated AR derivatives have so far not been described for the Thermoplasmatales, however, for euryarchaea of the orders Halobacteriales, Thermococcales, Methanopyrales and Methanosarcinales (e.g. Dawson et al, 2012;Gonthier et al, 2001;Hafenbradl et al, 1993;Nichols et al, 2004), with a broad range of growth temperatures. This indicates that the abundance of these compounds in strains S5…”
Section: Strains S5mentioning
confidence: 99%
“…(3) The crosslinking of the two acyl-chains of the lipids to yield macrocyclic archaeol or caldarchaeol derivatives by a covalent bond between the isoprenoid chains reduces the motion of the molecule creating a more closely-packed structure and increasing the membrane stability, creating an efficient barrier against water, proton and solute leakage (Dannenmuller et al 2000;Mathai et al 2001). (4) The increase in unsaturation along the isoprenoid chains of the lipids as a function of temperature (Nichols et al 2004) or salinity (Dawson et al 2012) has to date only been described in the psychrophilic methanogen Methanococcoides burtonii (Franzmann et al 1992;Nichols et al 2004), but unsaturated lipids have been characterized in several species of hyperthermophiles (Hafenbradl et al 1993;Gonthier et al 2001), which might indicate the occurrence of a similar adaptive strategy in hydrothermal vent organisms.…”
Section: Physiology and Adaptationmentioning
confidence: 99%