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.

doi:10.1021/jacs.6b10706.s005

ja6b10706_si_005.pdf (21.1 MB)

Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

journal contribution

posted on 2016-11-21, 00:00 authored by 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

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.