Premium
Enantioselective Total Synthesis of the Archaeal Lipid Parallel GDGT‐0 (Isocaldarchaeol) **
Author(s) -
Falk Isaac D.,
Gál Bálint,
Bhattacharya Ahanjit,
Wei Jeremy H.,
Welander Paula V.,
Boxer Steven G.,
Burns Noah Z.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202104051
Subject(s) - archaea , enantioselective synthesis , chemistry , glycerol , total synthesis , membrane , stereoselectivity , amphiphile , membrane lipids , stereoisomerism , stereochemistry , combinatorial chemistry , biochemistry , molecule , organic chemistry , catalysis , gene , copolymer , polymer
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 parallel GDGT‐0 and the synthesis and self‐assembly of derivatives bearing different polar groups.