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Journal of Lipid Research, Vol. 43, 1641-1651, October 2002
Copyright © 2002 by Lipid Research, Inc.
Crenarchaeol
: the characteristic core glycerol dibiphytanyl glycerol tetraether membrane lipid of cosmopolitan pelagic crenarchaeota
* Royal Netherlands Institute for Sea Research (NIOZ), Department of Marine Biogeochemistry and Toxicology, PO Box 59, 1790 AB Den Burg, The Netherlands
Newcastle University, Department of Fossil Fuels and Environmental Geochemistry, Drummond Building, Newcastle upon Tyne NE1 7RU, UK
University of Amsterdam, Faculty of Chemistry, Department of Organic Chemistry, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands
1 To whom correspondence should be addressed. e-mail: damste{at}nioz.nl
The basic structure and stereochemistry of the characteristic glycerol dibiphytanyl glycerol tetraether (GDGT) membrane lipid of cosmopolitan pelagic crenarchaeota has been identified by high field two-dimensional (2D)-NMR techniques. It contains one cyclohexane and four cyclopentane rings formed by internal cyclisation of the biphytanyl chains. Its structure is similar to that of GDGTs biosynthesized by (hyper)thermophilic crenarchaeota apart from the cyclohexane ring. These findings are consistent with the close phylogenetic relationship of (hyper)thermophilic and pelagic crenarchaeota based 16S rRNA. The latter group inherited the biosynthetic capabilities for a membrane composed of cyclopentane ring-containing GDGTs from the (hyper)thermophilic crenarchaeota. However, to cope with the much lower temperature of the ocean, a small but key step in their evolution was the adjustment of the membrane fluidity by making a kink in one of the bicyclic biphytanyl chains by the formation of a cyclohexane ring.
This prevents the dense packing characteristic for the cyclopentane ring-containing GDGTs membrane lipids used by hyperthermophilic crenarchaeota to adjust their membrane fluidity to high temperatures.
Abbreviations: APCI, atmospheric pressure chemical ionization; APT, attached proton test; COSY, correlated spectroscopy; DCM, dichloromethane; DEPT, distorsionless enhancement by polarization transfer; HMBC, heteronuclear multiple bond correlation; HMQC, heteronuclear multiple quantum correlation; GDGT, glycerol dibiphytanyl glycerol tetraether; MS, mass spectrometry; NOE, nuclear Overhauser effect; NOESY, nuclear Overhauser effect spectroscopy; 2D, two-dimensional; TOCSY, total correlation spectroscopy
Supplementary key words archaea • ether-bound biphytanes • ocean • ether lipids
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