title: Crenarchaeol: the characteristic core glycerol dibiphytanyl glycerol tetraether membrane lipid of cosmopolitan pelagic crenarchaeota.
abstract: 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.
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003198:Computer Simulation; D019615:Crenarchaeota / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry; D004075:Diglycerides / Q000737:chemistry*; D005995:Glyceryl Ethers / Q000737:chemistry*; D013058:Mass Spectrometry; D008560:Membrane Fluidity; D008563:Membrane Lipids / Q000737:chemistry* / Q000302:isolation & purification; D008958:Models, Molecular; D019906:Nuclear Magnetic Resonance, Biomolecular; D010802:Phylogeny; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D004075:Diglycerides; D005995:Glyceryl Ethers; D008563:Membrane Lipids