Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid
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- 作者：Jaron A. M. Mercer ; Carolyn M. Cohen ; Steven R. Shuken ; Anna M. Wagner ; Myles W. Smith ; Frank R. Moss III ; Matthew D. Smith ; Riku Vahala ; Alejandro Gonzalez-Martinez ; Steven G. Boxer ; Noah Z. Burns
- 刊名：Journal of the American Chemical Society
- 出版年：2016
- 出版时间：December 14, 2016
- 年：2016
- 卷：138
- 期：49
- 页码：15845-15848
- 全文大小：340K
- ISSN：1520-5126
文摘
Ladderane lipids produced by anammox bacteria constitute some of the most structurally fascinating yet poorly studied molecules among biological membrane lipids. Slow growth of the producing organism and the inherent difficulty of purifying complex lipid mixtures have prohibited isolation of useful amounts of natural ladderane lipids. We have devised a highly selective total synthesis of ladderane lipid tails and a full phosphatidylcholine to enable biophysical studies on chemically homogeneous samples of these molecules. Additionally, we report the first proof of absolute configuration of a natural ladderane.