title: Syntheses of 1,2-di-O-palmitoyl-sn-glycero-3-phosphocholine (DPPC) and analogs with 13C- and 2H-labeled choline head groups.
abstract: 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-di-O-palmitoyl-sn-glycero-3-phosphatidic acid (5) have been performed. The syntheses of 1,2-di-O-palmitoyl-sn-glycero-3-phospho[alpha-13C]choline (6a) and 1,2-di-O-palmitoyl-sn-glycero-3-phospho[beta-13C]choline (6b) were performed from labeled [1-13C]glycine (1a) in 52% overall yield and from [2-13C]glycine (1b) in 56% overall yield, respectively. 1,2-Di-O-palmitoyl-sn-glycero-3-phospho[N(C2H3)3]choline (9) was prepared from 2-aminoethanol in 39% overall yield. 1,2-Di-O-palmitoyl-sn-glycero-3-phospho[alpha-C2H2]choline (12) was prepared from N,N-dimethylglycine ethyl ester in 50% overall yield.
authors.affiliation: School of Pharmacy, University of Connecticut, Storrs 06269, USA.
authors.forename: S
authors.initials: S
authors.lastname: Lin
authors.forename: R I
authors.initials: RI
authors.lastname: Duclos
authors.forename: A
authors.initials: A
authors.lastname: Makriyannis
mesh_terms: D015060:1,2-Dipalmitoylphosphatidylcholine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D002247:Carbon Isotopes; D003903:Deuterium; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
chemical_list: D002247:Carbon Isotopes; D015060:1,2-Dipalmitoylphosphatidylcholine; D003903:Deuterium