title: Glycerol backbone conformation in phosphatidylcholines is primarily determined by the intramolecular stacking of the vicinally arranged acyl chains.
abstract: To analyse the effect of the altered glycerol backbone structure on the glycerophospholipid conformation, we have replaced the glycerol moiety by the rac-1,2,4-butanetriol residue in 1,2-diacyl-sn-glycero-3-phosphocholines (PC), and then analysed the resulting 1,2-dialkanoyloxy-rac-but-4-yl-[2-(trimethylammonium)ethyl] phosphates (1,2-bPC) and 1,3-dial-kanoyloxy-rac-but-4-yl-[2-(trimethylammonium)ethyl] phosphates (1,3-bPC) by high-resolution 1H- and 13C-NMR spectroscopy in both CDCI3 and D2O. The preferred conformation about the C1-C2 glycerol bond in PC was almost completely preserved in 1,2-bPC, but it was completely random in case of 1,3-bPC. Out of the three C-C bonds present in the butanetriol backbone of 1,3-bPC, only the C2-C3 bond experienced a restricted rotation. However, the conformational preference about this bond was virtually similar to that observed for the C1-C2 bond in PC. These results clearly demonstrate that the preferred conformation of the glycerol backbone is determined primarily by the intramolecular acyl chain stacking which essentially requires a vicinal arrangement of the acyl chains in glycerophospholipids.
authors.affiliation: Institute of Microbial Technology, Chandigarh, India.
authors.forename: A
authors.initials: A
authors.lastname: Arora
authors.forename: C M
authors.initials: CM
authors.lastname: Gupta
mesh_terms: D015060:1,2-Dipalmitoylphosphatidylcholine; D000478:Alkylation; D005990:Glycerol / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010713:Phosphatidylcholines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D010713:Phosphatidylcholines; D015060:1,2-Dipalmitoylphosphatidylcholine; D005990:Glycerol