Bis(monoaclyglycero)phosphate (BMP), also known as lysobisphosphatidic acid (LBPA), is a unique phospholipid highly enriched in a specific membrane domain of late endosomes. We synthesized 3,3’-dipalmitoyl bis (monoacylglycero) phosphate (diC16:0 BMP) with naturally occurring sn–1, sn–1’ stereoconfiguration and characterized the thermotropic phase behavior and the membrane properties by using differential scanning calorimetry (DSC), smalland wide-angle X-ray scattering, steady-state fluorescence anisotropy measurement and epifluorescence microscopy of monolayers. In DSC, DiC16:0 BMP displayed a higher melting temperature (52.0 ℃) and a higher molar enthalpy (17.3 kcal/mol) of main phase transition than those of corresponding PG (40.1 ℃ and 9.4 kcal/mol respectively). DiC16: 0 BMP also exhibited weakly energetic broad peak at 19.5 ℃. Wide-angle X-ray scattering revealed that the diC16: 0 BMP undergoes quasi-crystalline phase → tightly packed and partly oriented gel phase → liquid crystalline phase between 10 ℃ and 60 ℃ by passing two calorimetric transitions. Steady-state anisotropy measurements of 1,6- diphenyl-1,3,5-hexatriene (DPH) and 1-(4-trimethylammonium-phenyl)-6-phenyl-1,3,5-hexatriene (TMA-DPH) in diC16:0 BMP also indicated a high main transition temperature in BMP. The domain formation in monolayer showed that diC16: 0 BMP formed anisotropic domain shape while PG formed relatively circular domains. The present results, together with our recent results (Hayakawa, T., Hirano, Y., Makino, A., Michaud, S., Lagarde, M., Pageaux, JF., Doutheau, A., Ito, K., Fujisawa, T., Takahashi, H. and Kobayashi, T. (2006) Biochemistry, , 9198-9209) suggest the formation of strong inter-molecular hydrogen bonding between the BMP molecules in the membrane.
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