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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.

SUBMITTER: Holzheimer M

PROVIDER: S-EPMC8361987 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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

Holzheimer Mira M Sinninghe Damsté Jaap S JS Schouten Stefan S Havenith Remco W A RWA Cunha Ana V AV Minnaard Adriaan J AJ

Angewandte Chemie (International ed. in English) 20210630 32

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 synthe ...[more]

PMID: 34114718

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