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古菌脂质平行GDGT-0(异源钙古菌醇)的对映选择性全合成*

Enantioselective Total Synthesis of the Archaeal Lipid Parallel GDGT-0 (Isocaldarchaeol)*.

作者信息

Falk Isaac D, Gál Bálint, Bhattacharya Ahanjit, Wei Jeremy H, Welander Paula V, Boxer Steven G, Burns Noah Z

机构信息

Department of Chemistry, Stanford University, Stanford, CA, 94305, USA.

Department of Earth System Science, Stanford University, Stanford, CA, 94305, USA.

出版信息

Angew Chem Int Ed Engl. 2021 Aug 2;60(32):17491-17496. doi: 10.1002/anie.202104051. Epub 2021 Jun 11.

Abstract

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.

摘要

古菌甘油二植烷甘油四醚(GDGT)是自然界中发现的一些最不寻常的膜脂。这些两亲物是众多古菌膜的主要成分,其中一些是极端嗜热生物。由于其独特的结构,人们对研究这些分子的生物物理性质和生物合成产生了浓厚兴趣。然而,迄今为止,这些研究受到化学纯样品获取有限的阻碍。在此,我们报告了古菌四醚脂质平行GDGT-0的简洁且立体选择性合成以及带有不同极性基团的衍生物的合成与自组装。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f762/12103258/1bb3f199ac91/nihms-1705095-f0001.jpg

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