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 journalArticle

40 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 languageEnglish (US)
Pages (from-to)15845-15848
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number49
DOIs
StatePublished - Dec 14 2016

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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  • 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