Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision**

2021/06/11 by Mira Holzheimer, Jaap S. Sinninghe Damsté, Stefan Schouten +3 · 1 voice · 3 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · Medicine · #Carbohydrate Chemistry and Synthesis #Genomics and Phylogenetic Studies #Microbial Natural Products and Biosynthesis

paper · pdf · doi:10.1002/anie.202105384

openalex publication_date 2021/06/11 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/28

Abstract

Crenarchaeol 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.

Citations

• Phylogenetic structure of the prokaryotic domain: The primary kingdoms
• Towards a natural system of organisms: proposal for the domains Archaea, Bacteria, and Eucarya.

Cited by

• Total Synthesis of the Membrane Spanning Tetraether Lipid brGDGT Ia and Elucidation of Its Stereochemical Configuration
• Evaluating isoprenoidal hydroxylated GDGT-based temperature proxies in surface sediments from the global ocean
• Archaeal lipids trace ecology and evolution of marine ammonia-oxidizing archaea

Discussions

• Oh, it was really useful that this one in particular was synthesized doi.org/10.1002/anie... . Now there're only at least 20 other structures in the field not fully described 😅 [bsky, 2 points, 1 comments]

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