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

Angewandte Chemie
Mira HolzheimerAdriaan J. Minnaard

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.

References

Nov 1, 1977·Proceedings of the National Academy of Sciences of the United States of America·C R Woese, G E Fox
Aug 2, 1978·Journal of Molecular Evolution·C R WoeseG E Fox
Jun 1, 1990·Proceedings of the National Academy of Sciences of the United States of America·C R WoeseM L Wheelis
Jan 23, 1999·Current Opinion in Genetics & Development·E F DeLong
Dec 20, 2000·Proceedings of the National Academy of Sciences of the United States of America·S SchoutenJ S Damste
Oct 25, 2001·The Journal of Organic Chemistry·Grégory LecollinetDaniel Plusquellec
Oct 27, 2001·Journal of Natural Products·F NagashimaY Asakawa
Feb 1, 1996·Chemical Reviews·Barry M. Trost, David L. Van Vranken
Feb 22, 2002·Chemistry : a European Journal·Grégory LecollinetDaniel Plusquellec
Jun 16, 2004·Accounts of Chemical Research·Amos B Smith, Christopher M Adams
Aug 12, 2004·Journal of the American Chemical Society·Mickaëlle BrardDaniel Plusquellec
Mar 10, 2007·Microbiology and Molecular Biology Reviews : MMBR·Yosuke Koga, Hiroyuki Morii
Nov 4, 2008·The Journal of Organic Chemistry·Christian SmitAdriaan J Minnaard
Dec 7, 2010·Nature Reviews. Microbiology·Ricardo Cavicchioli
Jun 12, 2012·Nature Reviews. Microbiology·Jonathan LombardDavid Moreira
Jul 24, 2012·Applied and Environmental Microbiology·Jaap S Sinninghe DamstéChrista Schleper
Aug 29, 2012·Archaea : an International Microbiological Journal·Yosuke Koga
Aug 7, 2013·Biophysical Chemistry·Philippe M Oger, Anaïs Cario
May 8, 2014·Nature Reviews. Microbiology·Laura VillanuevaStefan Schouten
Oct 18, 2014·Journal of the American Chemical Society·Lei ZhangZheng Huang
Dec 17, 2014·Frontiers in Microbiology·Samta JainArnold J M Driessen
Sep 14, 2017·Journal of the American Chemical Society·Won Jun JangJaesook Yun
Oct 9, 2019·Proceedings of the National Academy of Sciences of the United States of America·Zhirui ZengPaula V Welander

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