Biomaterial Database

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. 1990

O H Abdelmageed, and R I Duclos, and E Abushanab, and A Makriyannis

Section of Medicinal Chemistry, University of Connecticut, Storrs.

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.

UI	MeSH Term	Description	Entries
D010713	Phosphatidylcholines	Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	Choline Phosphoglycerides,Choline Glycerophospholipids,Phosphatidyl Choline,Phosphatidyl Cholines,Phosphatidylcholine,Choline, Phosphatidyl,Cholines, Phosphatidyl,Glycerophospholipids, Choline,Phosphoglycerides, Choline
D010714	Phosphatidylethanolamines	Derivatives of phosphatidic acids in which the phosphoric acid is bound in ester linkage to an ethanolamine moiety. Complete hydrolysis yields 1 mole of glycerol, phosphoric acid and ethanolamine and 2 moles of fatty acids.	Cephalin,Cephalins,Ethanolamine Phosphoglyceride,Ethanolamine Phosphoglycerides,Ethanolamineglycerophospholipids,Phosphoglyceride, Ethanolamine,Phosphoglycerides, Ethanolamine
D002247	Carbon Isotopes	Stable carbon atoms that have the same atomic number as the element carbon but differ in atomic weight. C-13 is a stable carbon isotope.	Carbon Isotope,Isotope, Carbon,Isotopes, Carbon
D003903	Deuterium	The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	Deuterons,Hydrogen-2,Hydrogen 2
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer