Total synthesis of the alleged structure of crenarchaeol enables structure revision
- Author
- Mira Holzheimer, Jaap S. Sinninghe Damste, Stefan Schouten, Remco Havenith (UGent) , Ana V. Cunha and Adriaan J. Minnaard
- Organization
- 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.
- Keywords
- CATALYZED ENANTIOSELECTIVE HYDROBORATION, PHENYLGLYCINE METHYL-ESTER, ABSOLUTE-CONFIGURATION, TETRAETHER LIPIDS, INTACT POLAR, MEMBRANE, ARCHAEA, EVOLUTION, REAGENTS, CLEAVAGE, archaea, crenarchaeol, structure revision, tetraether lipid, total, synthesis
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-8756260
- MLA
- Holzheimer, Mira, et al. “Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 60, no. 32, 2021, pp. 17504–13, doi:10.1002/anie.202105384.
- APA
- Holzheimer, M., Sinninghe Damste, J. S., Schouten, S., Havenith, R., Cunha, A. V., & Minnaard, A. J. (2021). Total synthesis of the alleged structure of crenarchaeol enables structure revision. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 60(32), 17504–17513. https://doi.org/10.1002/anie.202105384
- Chicago author-date
- Holzheimer, Mira, Jaap S. Sinninghe Damste, Stefan Schouten, Remco Havenith, Ana V. Cunha, and Adriaan J. Minnaard. 2021. “Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 60 (32): 17504–13. https://doi.org/10.1002/anie.202105384.
- Chicago author-date (all authors)
- Holzheimer, Mira, Jaap S. Sinninghe Damste, Stefan Schouten, Remco Havenith, Ana V. Cunha, and Adriaan J. Minnaard. 2021. “Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 60 (32): 17504–17513. doi:10.1002/anie.202105384.
- Vancouver
- 1.Holzheimer M, Sinninghe Damste JS, Schouten S, Havenith R, Cunha AV, Minnaard AJ. Total synthesis of the alleged structure of crenarchaeol enables structure revision. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2021;60(32):17504–13.
- IEEE
- [1]M. Holzheimer, J. S. Sinninghe Damste, S. Schouten, R. Havenith, A. V. Cunha, and A. J. Minnaard, “Total synthesis of the alleged structure of crenarchaeol enables structure revision,” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 60, no. 32, pp. 17504–17513, 2021.
@article{8756260,
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.}},
author = {{Holzheimer, Mira and Sinninghe Damste, Jaap S. and Schouten, Stefan and Havenith, Remco and Cunha, Ana V. and Minnaard, Adriaan J.}},
issn = {{1433-7851}},
journal = {{ANGEWANDTE CHEMIE-INTERNATIONAL EDITION}},
keywords = {{CATALYZED ENANTIOSELECTIVE HYDROBORATION,PHENYLGLYCINE METHYL-ESTER,ABSOLUTE-CONFIGURATION,TETRAETHER LIPIDS,INTACT POLAR,MEMBRANE,ARCHAEA,EVOLUTION,REAGENTS,CLEAVAGE,archaea,crenarchaeol,structure revision,tetraether lipid,total,synthesis}},
language = {{eng}},
number = {{32}},
pages = {{17504--17513}},
title = {{Total synthesis of the alleged structure of crenarchaeol enables structure revision}},
url = {{http://doi.org/10.1002/anie.202105384}},
volume = {{60}},
year = {{2021}},
}
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