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 journalArticleScientificpeer-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 languageEnglish
Pages (from-to)15845-15848
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number49
DOIs
Publication statusPublished - 14 Dec 2016
MoE publication typeA1 Journal article-refereed

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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

    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

    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

    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