Synthesis of Glycosylphosphatidylinositol Anchors

The Chemical Synthesis of Glycosylphosphatidylinositol Anchors from Trypanosoma cruzi Trypomastigote Mucins... 

The synthesis of glycosylphosphatidylinositol (GPI) anchors of proteins, including Thy-1 of neurons and lymphocytes, is primarily carried out within the lumen of the rough endoplasmic reticulum. The anchor consists of a phosphatidylinositol-glucosamine-mannosey-ethanolamine phosphate core that is linked to the a-carboxyl of the carboxyterminal amino acid of a protein (Figure 16-12). This addition takes place within minutes of... 

Specific proteins can be covalently attached via a carbohydrate bridge to membrane-bound PI (glycosylphosphatidylinositol, or GPI). This allows GPI-anchored proteins rapid lateral mobility on the surface of the plasma membrane. A deficiency in the synthesis of GPI in hematopoietic cells results in a hemolytic disease, paroxysmal nocturnal hemoglobinuria. 

Conrad, R.M., Grogan, M.J., and Bertozzi, C.R., 2002, Stereloselective synthesis of myo-inositol via ring-closing metathesis A building block for glycosylphosphatidylinositol (GPI) anchor synthesis. Org. Lett. 4 1359-1361. 

Glycosylphosphatidylinositol (GPI) membrane anchors constitute a class of glycolipids that covalently link certain proteins to cell and virion surfaces [122,123]. A boost in their chemistry occurred in 1988 when Ferguson et al. reported the first covalent structure of a member of this family [124,125]. The first synthesis of a fully phosphorylated GPI, compound 246 (O Fig. 5), was accomplished by Fraser-Reid s group based entirely on NPG chemistry [126,127,128,129,130]. 

Baeschlin DK, Chaperon AR, Green LG, Hahn MG, Ince SJ, Ley SV. 1,2-Diacetals in synthesis total synthesis of a glycosylphosphatidylinositol anchor of Trypanosoma brucei. Chem Eur J 2000 6 172-186. 

Murakata C, Ogawa T. Stereoselective synthesis of glycobiosyl phosphatidy-linositol, a part structure of the glycosylphosphatidylinositol (GPI) anchor of Trypanosoma brucei. Carbohydr Res 1992 234 75-91. 

Walton, K. A., Hsieh, X., Gharavi, N., Wang, S., Wang, G., Yeh, M., Cole, A. L., and Berliner, J. A. 2003b. Receptors involved in the oxidized l-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphorylcholine-mediated synthesis of interleukin-8. A role for Toll-like receptor 4 and a glycosylphosphatidylinositol-anchored protein. 278, 29661-6. 

Berliner, J. A., Receptors involved in the oxidized l-palmitoyl-2-arachidonoyl-sw-glycero-3-phosphorylcholine-mediated synthesis of interleukin-8. A role for Toll-like receptor 4 and a glycosylphosphatidylinositol-anchored protein, 2003,... 

C. Sutterlin, M.V. Escribano, P. ferold P, Y. Maeda, M.J. Mazon, T. Kinoshita, R.T. Schwarz, and H. Riezman, Saccharomyces cerevisiae GPIIO, the functional homologue of human PIG-B, is required for glycosylphosphatidylinositol-anchor synthesis, Biochem. J. 1998, 332, 153 159. 

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