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

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

40 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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10.1021/jacs.6b10706

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Datasets

CCDC 1527453: Experimental Crystal Structure Determination

Boxer, S. G. (Contributor), Burns, N. Z. (Contributor), Cohen, C. M. (Contributor), Mercer, J. A. M. (Contributor), Shuken, S. R. (Contributor), Smith, M. W. (Contributor), Smith, M. W. (Contributor), Vahala, R. (Creator) & Wagner, A. M. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2017

DOI: 10.5517/ccdc.csd.cc1n8fp1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n8fp1&sid=DataCite

Dataset

CCDC 1527454: Experimental Crystal Structure Determination

Boxer, S. G. (Contributor), Burns, N. Z. (Contributor), Cohen, C. M. (Contributor), Mercer, J. A. M. (Contributor), Shuken, S. R. (Contributor), Smith, M. W. (Contributor), Smith, M. W. (Contributor), Vahala, R. (Creator) & Wagner, A. M. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2017

DOI: 10.5517/ccdc.csd.cc1n8fq2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n8fq2&sid=DataCite

Dataset

CCDC 1527452: Experimental Crystal Structure Determination

Boxer, S. G. (Contributor), Burns, N. Z. (Contributor), Cohen, C. M. (Contributor), Mercer, J. A. M. (Contributor), Shuken, S. R. (Contributor), Smith, M. W. (Contributor), Smith, M. W. (Contributor), Vahala, R. (Creator) & Wagner, A. M. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2017

DOI: 10.5517/ccdc.csd.cc1n8fn0, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n8fn0&sid=DataCite

Dataset

Cite this

Mercer, J. A. M., Cohen, C. M., Shuken, S. R., Wagner, A. M., Smith, M. W., Moss, F. R., Smith, M. D., Vahala, R., Gonzalez-Martinez, A., Boxer, S. G., & Burns, N. Z. (2016). Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid. Journal of the American Chemical Society, 138(49), 15845-15848. https://doi.org/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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Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid. / Mercer, Jaron A M; Cohen, Carolyn M.; Shuken, Steven R.; Wagner, Anna M.; Smith, Myles W.; Moss, Frank R.; Smith, Matthew D.; Vahala, Riku; Gonzalez-Martinez, Alejandro; Boxer, Steven G.; Burns, Noah Z.

In: Journal of the American Chemical Society, Vol. 138, No. 49, 14.12.2016, p. 15845-15848.

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

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AU - Moss, Frank R.

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