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Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

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    Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid
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    † Department of Chemistry, Stanford University, Stanford, California 94305, United States
    ‡ Department of Built Environment, School of Engineering, Aalto University, Aalto, FI-00076 Espoo, Finland
    *[email protected]
    *[email protected]
    *[email protected]
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2016, 138, 49, 15845–15848
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    https://doi.org/10.1021/jacs.6b10706
    Published November 21, 2016
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    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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    Cite this: J. Am. Chem. Soc. 2016, 138, 49, 15845–15848
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    https://doi.org/10.1021/jacs.6b10706
    Published November 21, 2016
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