Chapter 10 Chemical Synthesis of Glycosylphosphatidylinositol (GPI) Anchors

Enzymes

Volumn 26, Issue C, 2009, Pages 181-227

  Vishwakarma, Ram ^a   Ruhela, Dipali ^a  

^a NATIONAL INSTITUTE OF IMMUNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77954842998     PISSN: 18746047     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1874-6047(09)26010-0     Document Type: Review

References (55)

1. Ferguson M.A.J., Homans S.W., Dwek R.A., Rademacher T.W. Glycosyl phosphatidylinositol moiety that anchors Trypanosoma brucei variant surface glycoprotein to the membrane. Science 1988, 239:753-759.
2. Homans S.W., Ferguson M.A.J., Dwek R.A., Rademacher T.W., Anand R., Williams A.F. Complete structure of the glycosyl phosphatidylinositol membrane anchor of rat brain Thy-1 glycoprotein. Nature 1988, 333:269-272.
3. Orlean P., Menon A.K. Thematic review series: lipid posttranslational modifications. GPI anchoring of protein in yeast and mammalian cells, or: how we learned to stop worrying and love glycophospholipids. J Lipid Res 2007, 48:993-1011.
4. McConville M.J., Menon A.K. Recent developments in the cell biology and biochemistry of glycosylphosphatidylinositol. Mol Membr Biol 2000, 17:1-16.
5. McConville M.J., Ferguson M.A. The structure, biosynthesis and function of glycosylated phosphatidylinositols in the parasitic protozoa and higher eukaryotes. Biochem J 1993, 294:305-324.
6. Englund P.T. The structure and biosynthesis of glycosyl phosphatidylinositol protein anchors. Annu Rev Biochem 1993, 62:121-138.
7. Murakata C., Ogawa T. Synthetic studies on cell-surface glycans. Synthetic study on glycophosphatidyl inositol (GPI) anchor of Trypanosoma brucei: glycoheptaosyl core. Tetrahedron Lett 1990, 31:2439-2442.
8. Murakata C., Ogawa T. Synthetic studies on cell-surface glycans. Synthetic studies on glycophosphatidylinositol anchor: a highly efficient synthesis of glycobiosyl phosphatidylinositol through H-phosphonate approach. Tetrahedron Lett 1991, 32:101-104.
9. Murakata C., Ogawa T. Synthetic studies on cell-surface glycans. A total synthesis of GPI anchor of Trypanosoma brucei. Tetrahedron Lett 1991, 32:671-674.
10. Murakata C., Ogawa T. Synthetic studies on cell surface glycans.Stereoselective synthesis of glycobiosyl phosphatidylinositol, a part structure of the glycosylphosphatidyl inositol (GPI) anchor of Trypanosoma brucei. Carbohydr Res 1992, 234:75-91.
11. Murakata C., Ogawa T. Synthetic studies on cell-surface glycans. Stereo-selective total synthesis of the glycosyl phosphatidylinositol (GPI) anchor of Trypanosoma brucei. Carbohydr Res 1992, 235:95-114.
12. Baeschlin D.K., Chaperon A.R., Charbonneau V., Green L.G., Ley S.V., Lucking U., Walther E. Rapid assembly of oligosaccharides: total synthesis of a glycosyl phosphatidylinositol anchor of Trypanosoma brucei. Angew Chem Int Ed 1999, 37:3423-3428.
13. Baeschlin D.K., Chaperon A.R., Green L.G., Hahn M.G., Ince S.J., Ley S.V. 1,2-Diacetals in synthesis: total synthesis of a glycosylphosphatidylinositol anchor of Trypanosoma brucei. Chem Eur J 2000, 6:172-186.
14. Mallet A., Mallet J.M., Sinay P. The use of selenophenyl galactopyrano sides for the synthesis of α and β-(1→4-C-disaccharides. Tetrahedron Asymmetry 1994, 5:2593-2608.
15. Mayer T.G., Kratzer B., Schmidt R.R. Synthesis of a GPI anchor of the yeast Saccharomyces cerevisiae. Angew Chem Int Ed 1994, 33:2177-2181.
16. Mayer T.G., Schmidt R.R. Glycosylphosphatidylinositol (GPI) anchor synthesis based on versatile building blocks. Total synthesis of a GPI anchor of yeast. Eur J Org Chem 1999, 5:1153-1165.
17. Tailler D., Ferrieres V., Pekari K., Schmidt R.R. Synthesis of the glycosyl phosphatidylinositol anchor of rat brain Thy-1. Tetrahedron Lett 1999, 40:679-682.
18. Mayer T.G., Weingart R., Munstermann F., Kawada T., Kurzchalia T., Schmidt R.R. Synthesis of labeled glycosylphosphatidylinositol (GPI) anchors. Eur J Org Chem 1999, 10:2563-2571.
19. Pekari K., Tailler D., Weingart R., Schmidt R.R. Synthesis of the fully phosphorylated GPI anchor pseudohexasaccharide of Toxoplasma gondii. J Org Chem 2001, 66:7432-7442.
20. Pekari K., Schmidt R.R. A variable concept for the preparation of branched glycosylphosphatidylinositol anchors. J Org Chem 2003, 68:1295-1308.
21. Mootoo D.R., Konradsson P., Fraser-Reid B. n-Pentenyl glycosides facilitate a stereoselective synthesis of the pentasaccharide core of the protein membrane anchor found in Trypanosoma brucei. J Am Chem Soc 1989, 111:8540-8542.
22. Udodong U.E., Madsen R., Roberts C., Fraser-Reid B. A ready convergent synthesis of the heptasaccharide GPI membrane anchor of rat brain Thy-1 glycoprotein. J Am Chem Soc 1993, 115:7886-7887.
23. Stewart Campbell A., Fraser-Reid B. First synthesis of a fully phosphorylated GPI membrane anchor: rat brain Thy-1. J Am Chem Soc 1995, 117:10387-10388.
24. Roberts C., Madsen R., Fraser-Reid B. Studies related to synthesis of glycophosphatidylinositol membrane-bound protein anchors: n-pentenyl ortho esters for mannan components. J Am Chem Soc 1995, 117:1546-1553.
25. Madsen R., Udodong U.E., Roberts C., Mootoo D.R., Konradsson P., Fraser-Reid B. Studies related to synthesis of glycophosphatidylinositol membrane-bound protein anchors: convergent assembly of subunits. J Am Chem Soc 1995, 117:1554-1565.
26. Lu J., Jayaprakash K.N., Schlueter U., Fraser-Reid B. Synthesis of a malaria candidate glycosylphosphatidylinositol (GPI) structure: a strategy for fully inositol acylated and phosphorylated GPIs. J Am Chem Soc 2004, 126:7540-7547.
27. Chaplin D., Crout D.H.G., Bornemann S., Hutchinson D.W., Khan R. Conversion of 2-acetamido-2-deoxy-β-d-glucopyranose (N-acetylglucosamine) into 2-acetamido-2-deoxy-β-d-galactopyranose (N-acetylgalactosamine) using a biotransfor mation to generate a selectively deprotected substrate for SN2 inversion. J Chem Soc Perkin Trans 1 1992, 3:235-237.
28. Hori H., Nishida Y., Ohrui H., Meguro H. Regioselective de-O-benzylation with Lewis acids. J Org Chem 1989, 54:1346-1353.
29. Schofield L., Hewitt M.C., Evans K., Siomos M.A., Seeberger P.H. Synthetic GPI as a candidate anti-toxic vaccine in a model of malaria. Nature 2002, 418:785-789.
30. Hewitt M.C., Snyder D.A., Seeberger P.H. Rapid synthesis of a glycosyl phosphatidylinositol-based malaria vaccine using automated solid-phase oligosaccharide synthesis. J Am Chem Soc 2002, 124:13434-13436.
31. Seeberger P.H., Soucy R.L., Kwon Y.U., Snyder D.A., Kanemitsu T. A convergent, versatile route to two synthetic conjugate anti-toxin malaria vaccines. Chem Commun 2004, 15:1706-1707.
32. Liu X., Seeberger P.H. A Suzuki-Miyaura coupling mediated deprotection as key to the synthesis of a fully lipidated malarial GPI disaccharide. Chem Commun 2004, 15:1708-1709.
33. Liu X., Kwon Y.U., Seeberger P.H. Convergent synthesis of a fully lipidated glycosylphosphatidylinositol anchor of Plasmodium falciparum. J Am Chem Soc 2005, 127:5004-5005.
34. Kwon Y.U., Soucy R.L., Snyder D.A., Seeberger P.H. Assembly of a series of malarial glycosylphosphatidylinositol anchor oligosaccharides. Chem Eur J 2005, 11:2493-2504.
35. Kwon Y.U., Liu X., Seeberger P.H. Total syntheses of fully lipidated glycosyl phosphatidylinositol anchors of Toxoplasma gondii. Chem Commun 2005, 17:2280-2282.
36. Kamena F., Tamborrini M., Liu X., Kwon Y.U., Thompson F., Pluschke G., Seeberger P.H. Synthetic GPI array to study antitoxic malaria response. Nature Chem Biol 2008, 4:238-240.
37. Ali A., Gowda D.C., Vishwakarma R.A. A new approach to construct full-length glycosylphosphatidylinositols of parasitic protozoa and [4-deoxy-Man-III]-GPI analogues. Chem Commun 2005, 4:519-521.
38. Vishwakarma R.A., Menon A.K. Flip-flop of glycosylphosphatidylinositols (GPI's) across the ER. Chem Commun 2005, 4:453-455.
39. Ruhela D., Chatterjee P., Vishwakarma R.A. 1-Oxabicyclic β-lactams as new inhibitors of elongating MPT-a key enzyme responsible for assembly of cell-surface phosphoglycans of Leishmania parasite. Org Biomol Chem 2005, 3:1043-1048.
40. Vishwakarma R.A., Vehring S., Mehta A., Sinha A., Pomorski T., Herrmann A., Menon A.K. New fluorescent probes reveal that flippase-mediated flip-flop of phosphatidylinositol across the ER membrane does not depend on the stereochemistry of the lipid. Org Biomol Chem 2005, 3:1275-1283.
41. Ruhela D., Vishwakarma R.A. Iterative synthesis of Leishmania phosphoglycans by solution, solid-phase and polycondensation approaches without involving any glycosylation. J Org Chem 2003, 68:4446-4456.
42. Chawla M., Vishwakarma R.A. Alkylacylglycerolipid domain of GPI molecules of Leishmania is responsible for inhibition of PKC mediated c-fos gene expression. J Lipid Res 2003, 44:594-600.
43. Yashunsky D.V., Borodkin S., Ferguson M.A.J., Nikolaev A.V. The chemical synthesis of bioactive glycosylphosphatidylinositols from Trypanosoma cruzi containing unsaturated fatty acid in the lipid. Angew Chem Int Ed 2006, 45:468-474.
44. Xue J., Shao N., Guo Z. First total synthesis of a GPI-anchored peptide. J Org Chem 2003, 68:4020-4029.
45. Xue J., Guo Z. Convergent synthesis of a GPI Containing an acylated inositol. J Am Chem Soc 2003, 125:16334-16339.
46. Wu X., Guo Z. Convergent synthesis of a fully phosphorylated GPI anchor of the CD52 antigen. Org Lett 2007, 9:4311-4313.
47. Xue J., Guo Z. Convergent synthesis of an inner core GPI Sperm CD52. Bioorg Med Chem Lett 2002, 12:2015-2018.
48. Ruda K., Lindberg J., Garegg P.J., Oscarson S., Konradsson P. Synthesis of the Leishmania LPG core heptasaccharyl myo-inositol. J Am Chem Soc 2000, 122:11067-11072.
49. Lindberg J., Ohberg L., Garegg P.J., Konradsson P. Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances. Tetrahedron 2002, 58:1387-1398.
50. Hederos M., Konradsson P. Synthesis of the Trypanosoma cruzi LPPG heptasaccharyl myo-inositol. J Am Chem Soc 2006, 128:3414-3419.
51. Nikolaev A.V., Botvinko I.V., Ross A.J. Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis. Carbohydr Res 2006, 342:297-344.
52. Martin-Lomas M., Khiar N., Garcia S., Koessler J.L., Nieto P.M., Rademacher T.W. Inositolphosphoglycan mediators structurally related to glycosyl phosphatidylinositol anchors: synthesis, structure and biological activity. Chem Eur J 2000, 6:3608-3621.
53. Lopez-Prados J., Martin-Lomas M. Inositolphosphoglycan mediators: an effective synthesis of the conserved linear GPI anchor structure. J Carbohydr Chem 2005, 24:393-414.
54. Lopez-Prados J., Cuevas F., Reichardt N.C., de Paz J.L., Morales E.Q., Martin Lomas M. Design and synthesis of inositol-phospho-glycan putative insulin mediators. Org Biomol Chem 2005, 3:764-786.
55. Reichardt H.C., Martin-Lomas M. A practical solid-phase synthesis of glycosylphosphatidylinositol precursors. Angew Chem Int Ed 2003, 42:4674-4677.