Abstract
AbstractCrenarchaeol is a glycerol dialkyl glycerol tetraether lipid produced exclusively in Archaea of the phylum Thaumarchaeota. This membrane‐spanning lipid is undoubtedly the structurally most sophisticated of all known archaeal lipids and an iconic molecule in organic geochemistry. The 66‐membered macrocycle possesses a unique chemical structure featuring 22 mostly remote stereocenters, and a cyclohexane ring connected by a single bond to a cyclopentane ring. Herein we report the first total synthesis of the proposed structure of crenarchaeol. Comparison with natural crenarchaeol allowed us to propose a revised structure of crenarchaeol, wherein one of the 22 stereocenters is inverted.
Highlights
In 1990, Woese proposed to classify all living organisms in three domains of life: Archaea, Bacteria and Eukarya.[1]
The cell membrane of Archaea is built up of diether or membrane-spanning tetraether lipids containing isoprenoid chains, contrary to the straight chain fatty acid glycerol ester lipids found in Bacteria and Eukarya.[8,9]
The ether-linkages provide chemical stability against hydrolysis, and the presence of methyl-branches and cyclopentane moieties, which are formed by internal cyclization of the biphytanol chain,[13] leads to decreased membrane permeability, allowing growth at extreme pH, salinity, and temperature.[14]
Summary
In 1990, Woese proposed to classify all living organisms in three domains of life: Archaea, Bacteria and Eukarya.[1]. The ether-linkages provide chemical stability against hydrolysis, and the presence of methyl-branches and cyclopentane moieties, which are formed by internal cyclization of the biphytanol chain,[13] leads to decreased membrane permeability, allowing growth at extreme pH, salinity, and temperature.[14]
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