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.
| Original language | English |
|---|---|
| Pages (from-to) | 17504-17513 |
| Number of pages | 10 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 60 |
| Issue number | 32 |
| DOIs | |
| State | Published - Aug 2 2021 |
| Externally published | Yes |
Funding
The authors would like to thank Dr. J. Buter and E. Jonkheim (University of Groningen) for their contribution to the isolation of crenarchaeol. P. van der Meulen and Dr. J. Kemmink (University of Groningen) are acknowledged for their assistance in NMR measurements. This work was sponsored by NWO Exact and Natural Sciences for the use of supercomputer facilities and RWAH and AV thank S. Dolas (SURF, NL) for allowing to perform experiments on the experimental AMD platform kleurplaat, maintained and operated by SURF Open Innovation Lab. This project received funding to JSSD from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation program (grant agreement no. 694569, MICROLIPIDS).
Keywords
- archaea
- crenarchaeol
- structure revision
- tetraether lipid
- total synthesis