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Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision
preprintsubmitted on 22.12.2020, 11:43 and posted on 23.12.2020, 08:18 by Mira Holzheimer, Jaap S. Sinninghe Damsté, Stefan Schouten, Adriaan J. Minnaard
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.