Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

Research output: Contribution to journalArticleScientificpeer-review


  • 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 units

  • Stanford University


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
Issue number49
Publication statusPublished - 14 Dec 2016
MoE publication typeA1 Journal article-refereed

ID: 10372491