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Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision

23 December 2020, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

This study describes the first asymmetric total synthesis of the proposed structure of the archaeal membrane-spanning tetraether lipid crenarchaeol. The synthetic material was compared by NMR and GC-MS analysis with natural crenarchaeol. Detailed NMR analysis ultimately enabled the structure revision of crenarchaeol, identifying one out of 22 sterecenters to be inverted.

Keywords

Total Synthesis
Structure Revision
archaeal GDGT
Asymmetric Synthesis

Supplementary materials

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Description
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Supporting Information HRMS spectra Appendix
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Supporting Information NMR spectra Appendix
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Supporting Information Procedures
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Now Published

Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision** [opens in a new tab]
Mira Holzheimer, Jaap S. Sinninghe Damsté, Stefan Schouten, Remco W. A. Havenith, Ana V. Cunha, Adriaan J. Minnaard journal article
Angewandte Chemie International Edition , Volume 60, Issue 32
Online publication date: Jun 30, 2021

Version History

Dec 23, 2020 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.13475928.v1
D O I: 10.26434/chemrxiv.13475928.v1 [opens in a new tab]

Author’s competing interest statement

The authors declare no conflict of interest

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