88035-56-7Relevant academic research and scientific papers
Phospholipids Chiral at Phosphorus. 5. Synthesis and Configurational Analysis of Chiral Phosphatidylethanolamine
Bruzik, Karol,Tsai, Ming-Daw
, p. 747 - 754 (2007/10/02)
We report the synthesis and configurational analysis of 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE) chirally labeled with 17O and 18O at the phosphate head group.Condensation of (S)-1,2-dipalmitoyl-sn-glycerol, P17OCl3, and N-(1-phenylethyl)-2-aminoethanol gives a diastereomeric mixture of cyclic oxazaphospholidines.The two diastereomers were separated by coloumn chromatography.Ring opening with H218O followed by hydrogenolysis with H2/Pd gives (Rp)- and (Sp)-DPPE.The relative configuration and isotopic enrichments of DPPE can be analyzed by 31P NMR following silylation of DPPE.To determine the absolute configuration, the two diastereomers of DPPE are converted, by a combined organic and biochemical procedure, into (Rp)- and (Sp)-1-phospho-(R)-propane-1,2-diol, with all P-O bonds intact.The configuration of the latter compound is then analyzed by 31P NMR as reported previously (Buchwald, S.L.; Knowles, J.R.J.Am.Chem.Soc. 1980, 102, 6601-6603).
