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

M. Holzheimer; J.S. Sinninghe Damsté; S. Schouten; R.W.A. Havenith; A.V. Cunha; A.J. Minnaard

doi:10.1002/anie.202105384

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

M. Holzheimer
, J.S. Sinninghe Damsté
, S. Schouten
, R.W.A. Havenith
, A.V. Cunha
, A.J. Minnaard^*

^*Corresponding author for this work

Royal Netherlands Institute for Sea Research - NIOZ
University of Groningen
extern

Research output: Contribution to journal › Article › Academic › peer-review

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	https://doi.org/10.1002/anie.202105384
Publication status	Published - 2 Aug 2021

Bibliographical note

Cited By :10

Export Date: 24 November 2023

Access to Document

10.1002/anie.202105384Licence: CC BY

Angew Chem Int Ed - 2021 - Holzheimer - Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure RevisionFinal published version, 2.15 MBLicence: CC BY

Cite this

@article{78f8534f4f384da794fde7b04019d6ee,

title = "Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision**",

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 = "M. Holzheimer and \{Sinninghe Damst{\'e}\}, J.S. and S. Schouten and R.W.A. Havenith and A.V. Cunha and A.J. Minnaard",

note = "Cited By :10 Export Date: 24 November 2023",

year = "2021",

month = aug,

day = "2",

doi = "10.1002/anie.202105384",

language = "English",

volume = "60",

pages = "17504--17513",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "32",

}

TY - JOUR

T1 - Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision**

AU - Holzheimer, M.

AU - Sinninghe Damsté, J.S.

AU - Schouten, S.

AU - Havenith, R.W.A.

AU - Cunha, A.V.

AU - Minnaard, A.J.

N1 - Cited By :10 Export Date: 24 November 2023

PY - 2021/8/2

Y1 - 2021/8/2

N2 - 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.

AB - 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.

U2 - 10.1002/anie.202105384

DO - 10.1002/anie.202105384

M3 - Article

SN - 1433-7851

VL - 60

SP - 17504

EP - 17513

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 32

ER -

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

Abstract

Bibliographical note

Access to Document

Fingerprint

Cite this