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

^*Corresponding author for this work

Stanford University

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

82 Citations (Scopus)

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
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
Publication status	Published - 14 Dec 2016
MoE publication type	A1 Journal article-refereed

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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.}",

year = "2016",

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doi = "10.1021/jacs.6b10706",

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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.

UR - http://www.scopus.com/inward/record.url?scp=85006247373&partnerID=8YFLogxK

U2 - 10.1021/jacs.6b10706

DO - 10.1021/jacs.6b10706

M3 - Article

AN - SCOPUS:85006247373

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VL - 138

SP - 15845

EP - 15848

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

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CCDC 1527454: Experimental Crystal Structure Determination

CCDC 1527455: Experimental Crystal Structure Determination

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Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

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CCDC 1527453: Experimental Crystal Structure Determination

CCDC 1527454: Experimental Crystal Structure Determination

CCDC 1527455: Experimental Crystal Structure Determination

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