Specific deuterium labeling of archaeal 36-membered macrocyclic diether lipid

Article abstract of DOI:10.1246/bcsj.71.2419

Described in this paper is a practical synthesis of the specifically deuterated 36-membered macrocyclic diether lipid 4 and its acyclic deuterated counterpart 5, both of which are essential to the detailed biophysical studies of the conformational order of phospholipids in vesicles. The synthesis of 4 was principally composed of the preparation of deuterated diether 15, subsequent macrocyclization of the crucial dialdehyde 21 by McMurry coupling, and final transformation into the phosphocholine derivative. The acyclic deuterated counterpart 5 was also synthesized from the common intermediary tosylate 16.