CHAIN SUBSTITUTED POLYMERIZABLE ETHER LIPIDS - SYNTHESIS OF SORBYL AND DIACETYLENIC ETHER GLYCEROPHOSPHOCHOLINE

Three novel polymerizable ether lipids, 1,2-0-bis[10(2',4'-hexadienoyloxy)decyl]-rac, 1,2-0-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 (-)-l-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-degrees, 27.6-degrees and 30.0-degrees-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.