SYNTHESES OF 1,2-DI-O-PALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE (DPPC) AND ANALOGS WITH C-13-LABELED AND H-2-LABELED CHOLINE HEAD GROUPS

The syntheses of four head group labeled analogs of 1,2-di-O-palmitoyl -sn-glycero-3-phosphocholine (DPPC) (6) by a general method from 1,2-d i-O-palmitoyl-sn-glycero-3-phosphatidic acid (5) have been performed. The syntheses of -palmitoyl-sn-glycero-3-phospho[alpha-C-13]choline (6 a) and O-palmitoyl-sn-glycero-3-phospho[beta-C-13]choline (6b) were pe rformed from labeled [1-C-13]glycine (1a) in 52% overall yield and fro m [2-C-13]glycine (1b) in 56%, overall yield, respectively. itoyl-sn-g lycero-3-phospho[N((CH3)-H-2)(3)]choline (9) was prepared from 2-amino ethanol in 39% overall yield. itoyl-sn-glycero-3-phospho[alpha-(CH2)-H -2]choline (12) was prepared from N,N-dimethylglycine ethyl ester in 5 0% overall yield. (C) 1997 Elsevier Science Ireland Ltd.