Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

被引：73

作者：

Mercer, Jaron A. M. ^{[1
]}

Cohen, Carolyn M. ^{[1
]}

Shuken, Steven R. ^{[1
]}

Wagner, Anna M. ^{[1
]}

Smith, Myles W. ^{[1
]}

Moss, Frank R., III ^{[1
]}

Smith, Matthew D. ^{[1
]}

Vahala, Riku ^{[2
]}

Gonzalez-Martinez, Alejandro ^{[2
]}

Boxer, Steven G. ^{[1
]}

Burns, Noah Z. ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

[2] Aalto Univ, Sch Engn, Dept Built Environm, FI-00076 Espoo, Finland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 49期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

ANAMMOX BACTERIA; MEMBRANE-LIPIDS; ENANTIOSELECTIVE SYNTHESIS; BIOPHYSICAL PROPERTIES; RING-SYSTEMS; IDENTIFICATION; IRRADIATION; BIOREACTOR; FORM; TOOL;

D O I：

10.1021/jacs.6b10706

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：15845 / 15848

页数：4

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