Bis monoacylglycero phosphate

Bis(monoacylglycero)phosphate (BMP) species are isomeric to PG species. In BMP, two FA chains are acylated to different glycerol molecules, whereas these FA chains are located in one glycerol in PG species. BMP plays an important role in normal lysosomal/endosomal functions in cells [62]. It has become evident that BMP is involved in the pathology of lysosomal storage diseases such as Niemann-Pick C disease (cholesterol accumulation) and certain drug-induced lipidoses [63,64]. Dys-regulation of BMP metabolism and hence of cholesterol homeostasis may also be relevant to atherosclerosis [64]. 

These distinct features can be used to readily identify the isomeric species of PG and BMP as recently conducted [65]. 

---

Hayakawa, T., Makino, A., Murate, M., Sugimoto, L, Hashimoto, Y., Takahashi, H., Ito, K., Fujisawa, T., Matsuo, H., and Kobayashi, T. 2007. pH-dependent formation of membranous cytoplasmic bodylike structure of ganglioside G(ml)/bis(monoacylglycero)phosphate mixed membranes, Biophys J 92, L13-L15. 

Frederick, T. E., Chebukati, J. N., Mair, C. E., Goff, R C., and Fanucci, G. E. 2009. Bis(monoacylglycero) phosphate forms stable small lamellar vesicle structures Insights into vesicular body formation in endosomes, Biophys 96,1847-1855. 

A high-yielding synthesis of (S, 5)-3,3 -bis(monoacylglycero)phosphate derivatives (46-53) that allowed incorporation of a range of different saturated and perdeuterated acyl chains at a late stage has been developed by Best and Rowland. 

Figure 8. Model for the lysosomal degradation of a membrane-bound glycosphingoUpid by water-soluble lysosomal exohydrolases and membrane-active activator proteins. This example illustrates the degradation of ganglioside GM2 by P-hexosaminidase A and GM2-activator protein. BMP, bis (monoacylglycero)phosphate.

Amidon, B, Brown, A and Waite, M (1996) Transacylase and phospholipases in the synthesis of bis(monoacylglycero)phosphate. Biochemistry, 35, 13995-14002. 

Hulfin-Matsuda, R, Luquain-Costaz, C., Bouvier, J. and Delton-Vandenbroucke, I. (2009) Bis(monoacylglycero)phosphate, a peculiar phospholipid to control the fate of cholesterol Implications in pathology. Prostaglandins Leukot. Essent. Fatty Acids 81, 313-324. 

Phosphatidylglycerol is also the main precursor of bis(monoacylglycero)-phosphate although diphosphatidylglycerol can also function thus. Acyl-phosphatidylglycerol is also found in small amounts in bacteria. Both these derivatives of phosphatidylglycerol have their acyl groups donated from other phospholipids rather than from acyl-CoA. 

Hostetler, K.Y. (1982) Polyglycerophospholipids phosphatidylglycerol, diphos-phatidylglycerol and bis(monoacylglycero) phosphate in Phospholipids (eds J.N. Hawthorne and G.B. Ansell), Elsevier, Amsterdam, pp. 215-261. 

The D-camphor bisketal derivative (32) of natural mammalian lipid bis(monoacylglycero)phosphate (BMP) has been synthesised to identify the stereochemical configuration of its diglycerophosphate (DGP) backbone by NMR spectroscopy. As reference materials the sn-1,1 (33), sn-3,3 (34), and sn-3,1 (35) DGP analogues have also been prepered. ... 

---