Chirospecific syntheses of 2H- and 13C-labeled 1-O-alkyl-2-O-alkyl'-sn-glycero-3-phosphoethanolamines and 1-O-alkyl-2-O-alkyl'-sn-glycero-3-phosphocholines.
A convenient sequence for the synthesis of 1-O-alkyl-2-O-alkyl'-sn-glycero-3-phospholipids was demonstrated starting from 2,3-O-isopropylidene-sn-glycerol, which was first alkylated with 1-bromohexadecane, then converted to the corresponding benzylidene analog. Other less convenient methods to prepare 2,3-O-benzylidene-1-O-hexadecyl-sn-glycerol were also investigated. The key step in the synthesis was the reduction of 2,3-O-benzylidene-1-O-hexadecyl-sn-glycerol with lithium aluminum hydride-aluminum chloride to give 3-O-benzyl-1-O-hexadecyl-sn-glycerol as the major product in 79% yield. The syntheses of 1-O-hexadecyl-2-O-hexadecyl-(1',1'-d2,-sn-glycero-3-phosphoethanolamine and 1-O-hexadecyl-2-O-hexadecyl-(1'-13C)-sn-glycero-3-phosphoethanolamine as well as the correspondingly labeled sn-glycero-3-phosphocholine analogs were then performed. The optical purities of the synthetic intermediates and the ether lipids were established by a novel 1H-NMR method.
Abdelmageed
O H
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Section of Medicinal Chemistry, University of Connecticut, Storrs.
Duclos
R I
RI
Abushanab
E
E
Makriyannis
A
A
D002247:Carbon Isotopes; D003903:Deuterium; D010713:Phosphatidylcholines / Q000138:chemical synthesis*; D010714:Phosphatidylethanolamines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D002247:Carbon Isotopes; D010713:Phosphatidylcholines; D010714:Phosphatidylethanolamines; D003903:Deuterium