Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

Jaron A.M. Mercer; Carolyn M. Cohen; Steven R. Shuken; Anna M. Wagner; Myles W. Smith; Frank R. Moss; Matthew D. Smith; Riku Vahala; Alejandro Gonzalez-Martinez; Steven G. Boxer; Noah Z. Burns

doi:10.1021/jacs.6b10706

Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

Jaron A.M. Mercer, Carolyn M. Cohen, Steven R. Shuken, Anna M. Wagner, Myles W. Smith, Frank R. Moss, Matthew D. Smith, Riku Vahala, Alejandro Gonzalez-Martinez, Steven G. Boxer, Noah Z. Burns

Research output: Contribution to journal › Article › peer-review

70 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	15845-15848
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	49
DOIs	https://doi.org/10.1021/jacs.6b10706
State	Published - Dec 14 2016
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.6b10706

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title = "Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid",

abstract = "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.",

author = "Mercer, {Jaron A.M.} and Cohen, {Carolyn M.} and Shuken, {Steven R.} and Wagner, {Anna M.} and Smith, {Myles W.} and Moss, {Frank R.} and Smith, {Matthew D.} and Riku Vahala and Alejandro Gonzalez-Martinez and Boxer, {Steven G.} and Burns, {Noah Z.}",

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T1 - Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

AU - Mercer, Jaron A.M.

AU - Cohen, Carolyn M.

AU - Shuken, Steven R.

AU - Wagner, Anna M.

AU - Smith, Myles W.

AU - Moss, Frank R.

AU - Smith, Matthew D.

AU - Vahala, Riku

AU - Gonzalez-Martinez, Alejandro

AU - Boxer, Steven G.

AU - Burns, Noah Z.

PY - 2016/12/14

Y1 - 2016/12/14

N2 - 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.

AB - 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.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 49

ER -

Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

Abstract

ASJC Scopus subject areas

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