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Enantioselective Total Synthesis of the Archaeal Lipid Parallel GDGT-0

preprint
revised on 22.03.2021, 22:01 and posted on 23.03.2021, 13:15 by Isaac D. Falk, Bálint Gál, Ahanjit Bhattacharya, Jeremy H. Wei, Paula V. Welander, Steven Boxer, Noah Burns
Archaeal glycerol dibiphytanyl glycerol tetraethers (GDGT) are some of the most unusual membrane lipids identified in nature. These amphiphiles are the major constituents of the membranes of numerous Archaea, some of which are extremophilic organisms. Due to their unique structures, there has been significant interest in studying both the biophysical properties and the biosynthesis of these molecules. However, these studies have thus far been hampered by limited access to chemically pure samples. Herein, we report a concise and stereoselective synthesis of the archaeal tetraether lipid GDGT-0 and the synthesis and self-assembly of derivatives bearing different polar groups.

Funding

NSF CHE-1846512

NSF MCB-1915727

NIH GM118044

NASA 19-EXO19-0050

Center for Molecular Analysis and Design, Stanford

NSF ECCS-1542152

History

Email Address of Submitting Author

nburns@stanford.edu

Institution

Stanford University

Country

USA

ORCID For Submitting Author

0000-0003-1064-4507

Declaration of Conflict of Interest

No conflicts of interest

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