Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid

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.