Chain substituted polymerizable ether lipids: synthesis of sorbyl and diacetylenic ether glycerophosphocholine

Abstract Three novel polymerizable ether lipids, 1,2- O -bis[10(2′,4′-hexadienoyloxy)decyl]-rac, 1,2- O -bis(10,12-tricosadiynyl)-rac, and (−)-2,3- O -bis(10,12-tricosadiynyl)-sn-glycero-1-phosphocholine, were synthesized from 3- O -benzyl- rac , 3- O -trityl- rac and (−)-1- O -trityl- sn -glycerol as starting materials, respectively. All the reactions employed in these multi-step syntheses are straightforward giving an overall yield of 21% for the sorbyl, 42% for the racemic diacetylenic and 44% for the chiral diacetylenic lipid. All the lipids form bilayer assemblies on hydration and show transitions from gel to liquid-crystalline phases at 11.4°, 27.6° and 30.0°C, respectively. Bilayer assemblies of each are photoreactive and are readily polymerized by irradiation with 254 nm light. Tubules of the chiral diacetylenic ether lipid were observed.