AuBr3 mediated glycosidations: Synthesis of tetrasaccharide motif of the Leishmania donovani lipophosphoglycan

Glycoconjugate Journal

Volumn 29, Issue 4, 2012, Pages 221-230

  Sureshkumar, Gopalsamy ^a   Hotha, Srinivas ^a  

^a Indian Institute if Science Education and Research   (India)

Author keywords

Glycosidation; Gold catalysis; Leishmania; Lipophosphoglycan; Orthoester; Tetrasaccharide

Indexed keywords

3,4,6 TRI O BENZYL BETA DEXTRO MANNOPYRANOSE 1,2 (PROP 2 YNYL ORTHOACETATE); 3,4,6 TRI O BENZYL BETA DEXTRO MANNOPYRANOSE 1,2 (PROP 2 YNYL ORTHOBENZOATE); 3,6 DI O ACETYL 4 O (2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL) ALPHA DEXTRO GLUCOPYRANOSE 1,2 (PROP 2 YNYL ORTHOACETATE); 3,6 DI O BENZYL 4 O (2,3,4,6 TETRA O BENZYL BETA DEXTRO GALACTOPYRANOSYL) ALPHA DEXTRO GLUCOPYRANOSE 1,2 (PROP 2 YNYL ORTHOACETATE); ACETYL 11 AZIDO THIOUNDECANE; BROMIDE; CARBOHYDRATE DERIVATIVE; GOLD BROMIDE; LIPOPHOSPHOGLYCAN; PROP 2 YNYL 2 O (2 O ACETYL 3,4,6 TRI O BENZYL ALPHA DEXTRO MANNOPYRANOSYL) 3,6 DI O BENZYL 4 O (2,3,4,6 TETRA O BENZYL BETA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO MANNOPYRANOSIDE; PROP 2 YNYL 2 O (2 O BENZOYL 3,4,6 TRI O BENZYL ALPHA DEXTRO MANNOPYRANOSYL) 3,6 DI O BENZYL 4 O (2,3,4,6 TETRA O BENZYL BETA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO MANNOPYRANOSIDE; PROP 2 YNYL 2 O (3,4,6 TRI O BENZYL ALPHA DEXTRO MANNOPYRANOSYL) 3,6 DI O BENZYL 4 O (2,3,4,6 TETRA O BENZYL BETA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO MANNOPYRANOSIDE; PROP 2 YNYL 2 O [2 O (2 O ACETYL 3,4,6 TRI O BENZYL ALPHA DEXTRO MANNOPYRANOSYL) 3,4,6 TRI O BENZYL ALPHA DEXTRO MANNOPYRANOSYL] 3,6 DI O BENZYL 4 O (2,3,4,6 TETRA O BENZYL BETA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO MANNOPYRANOSIDE; PROP 2 YNYL 3,6 DI O BENZYL 4 O (2,3,4,6 TETRA O BENZYL BETA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO GLUCOPYRANOSIDE; PROP 2 YNYL 3,6 DI O BENZYL 4 O (2,3,4,6 TETRA O BENZYL BETA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO MANNOPYRANOSIDE; TETRASACCHARIDE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; BROMINATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CONTROLLED STUDY; ENZYME ANALYSIS; ENZYME STRUCTURE; ENZYME SYNTHESIS; GLYCOSIDATION; ISOMERIZATION; LEISHMANIA DONOVANI; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SAPONIFICATION;

GLYCOSIDES; GLYCOSPHINGOLIPIDS; GLYCOSYLATION; GOLD COMPOUNDS; LEISHMANIA DONOVANI; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES;

LEISHMANIA DONOVANI;

EID: 84862584580     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-012-9400-7     Document Type: Article

References (54)

1. Herwaldt, B.L.: Leishmaniasis. Lancet 354, 1191-1199 (1999)
2. http://www.who.int/topics/leishmaniasis/en/
3. Sacks, D.L.: Metacyclogenesis in Leishmania promastigotes. Exp. Parasitol. 69, 100-103 (1989)
4. McNeely, T.B., Tolson, D.L., Pearson, T.W., Turco, S.J.: Characterization of Leishmania donovani variant clones using antilipophosphoglycan monoclonal antibodies. Glycobiology 1, 63-69 (1990)
5. Beverley, S.M., Turco, S.J.: Lipophosphoglycan (LPG) and the identification of virulence genes in the protozoan parasite Leishmania. Trends Microbiol. 6, 35-40 (1998)
6. Turco, S.J., Descoteaux, A.: The Lipophosphoglycan of Leishmania Parasites. Annu. Rev. Microbiol. 46, 65-92 (1992)
7. 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 239, 753-759 (1988)
8. 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 333, 269-272 (1988)
9. Ferguson, M.A.J., Williams, A.F.: Cell-surface anchoring of proteins via glycosyl-phosphatidylinositol structures. Annu. Rev. Biochem. 57, 285-320 (1988)
10. Low, M.G.: Biochim. Biophys. Acta 988, 427-454 (1989)
11. Thomas, J.R., Dwek, R.A., Rademacher, T.W.: Structure, biosynthesis, and function of glycosylphosphatidylinositols. Biochemistry 29, 5413-5422 (1990)
12. Cross, G.A.M.: Glycolipid anchoring of plasma membrane proteins. Annu. Rev. Cell. Bio. 6, 1-39 (1990)
13. McConville, M.J.: Glycosylated-phosphatidylinositols as virulence factors in Leishmania. Cell Bio. Intl. Rep. 15, 779-798 (1991)
14. McConville, M.J., Ferguson, M.A.J.: The structure, biosynthesis and function of glycosylated phosphatidylinositols in the parasitic protozoa and higher eukaryotes. Biochem. J. 294, 305-324 (1993)
15. Englund, P.T.: The structure and biosynthesis of glycosyl phosphatidylinositol protein anchors. Annu. Rev. Biochem. 62, 121-138 (1993)
16. Saltiel, A.R., Fox, J.A., Sherline, P., Cuatrecasas, P.: Insulinstimulated hydrolysis of a novel glycolipid generates modulators of cAMP phosphodiesterase. Science 233, 967-972 (1986)
17. Tolsen, D.J., Turco, S.J., Beecroft, R.P., Pearson, T.W.: The immunochemical structure and surface arrangement of Leishmania donovani lipophosphoglycan determined using monoclonal antibodies. Mol. Biochem. Parasitol. 35, 109-118 (1989)
18. Chan, B.L., Chao, M.V., Saltiel, A.R.: Nerve growth factor stimulates the hydrolysis of glycosylphosphatidylinositol in PC-12 cells: a mechanism of protein kinase C regulation. Proc. Natl. Acad. Sci. U.S.A. 86, 1756-1760 (1989)
19. Eardley, D.D., Koshland, M.E.: Glycosylphosphatidylinositol: a candidate system for interleukin-2 signal transduction. Science 251, 78-81 (1991)
20. Pimento, P.F.P., Saraiva, E.M.B., Sacks, D.L.: The comparative fine structure and surface glycoconjugate expression of three life stages of Leishmania major. Exp. Parasitol. 72, 191-204 (1991)
21. Nikolaev, A.V., Rutherford, T.J., Ferguson, M.A.J., Brimacombe, J.S.: The chemical synthesis of Leishmania donovani phosphoglycan fragments. Bioorg. Med. Chem. Lett. 4, 785-788 (1994)
22. Nikolaev, A.V., Chudek, J.A., Ferguson, M.A.: The chemical synthesis of Leishmania donovani phosphoglycan via polycondensation of a glycobiosyl hydrogenphosphonate monomer. Carbohydr. Res. 272, 179-189 (1995)
23. Arasappan, A., FraserReid, B.: n-Pentenyl glycoside methodology in the stereoselective construction of the tetrasaccharyl cap portion of Leishmania lipophosphoglycan. J. Org. Chem. 61, 2401-2406 (1996)
24. Nikolaev, A.V., Watt, G.M., Ferguson, M.A.J., Brimacombe, J.S.: Parasite glycoconjugates. Part 6.1 Chemical synthesis of phosphorylated penta- and hepta-saccharide fragments of Leishmania major antigenic lipophosphoglycan. J. Chem. Soc., Perkin Trans 1, 969-980 (1997)
25. Higson, A.P., Tsvetkov, Y.E., Ferguson, M.A.J., Nikolaev, A.V.: The synthesis of Leishmania major phosphoglycan fragments. Tetrahedron Lett. 40, 9281-9284 (1999)
26. Ruda, K., Lindberg, J., Garegg, P.J., Oscarson, S., Konradsson, P.: Synthesis of the Leishmania LPG Core Heptasaccharyl myo- Inositol. J. Am. Chem. Soc 122, 11067-11072 (2000)
27. Upreti, M., Ruhela, D., Vishwakarma, R.A.: Synthesis of the tetrasaccharide cap domain of the antigenic lipophosphoglycan of Leishmania donovani parasite. Tetrahedron 56, 6577-6584 (2000)
28. Hewitt, M.C., Seeberger, P.H.: Solution and solid-support synthesis of a potential Leishmaniasis carbohydrate vaccine. J. Org. Chem. 66, 4233-4243 (2001)
29. Hewitt, M.C., Seeberger, P.H.: Automated solid-phase synthesiso f a branched Leishmania cap tetrasaccharide. Org Lett. 3, 3699-3702 (2001)
30. Yashunsky, D.V., Higson, A.P., Ross, A.J., Nikolaev, A.V.: An efficient and stereoselective synthesis of β-D-Arap-(1→2)-β-DGalp-( 1→3)-β-D-Galp-(1→4)-α-D-Manp, a tetrasaccharide fragment of Leishmania majorlipophosphoglycan. Carbohydr. Res. 336, 243-248 (2001)
31. Ruhela, D., Vishwakarma, R.A.: Efficient synthesis of the antigenic phosphoglycans of the Leishmaniaparasite. Chem. Commun. 2024-2025 (2001)
32. Gandolfi-Donadio, L., Gallo-Rodriguez, C., de Lederkremer, R.M.: Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-man, a terminal trisaccharide of Leishmania type-2 glycoinositolphospholipids. J. Org. Chem. 67, 4430-4435 (2002)
33. Ruhela, D., Vishwakarma, R.A.: A facile and novel route to the antigenic branched phosphoglycan of the protozoan Leishmania major parasite. Tetrahedron Lett. 45, 2589-2592 (2004)
34. Higson, A.P., Ross, A.J., Tsvetkov, Y.E., Routier, F.H., Sizova, O.V., Ferguson, M.A.V., Nikolaev, M.A.V.: Synthetic fragments of antigenic lipophosphoglycans from Leishmania major and Leishmania mexicana and their use for characterisation of the Leishmania elongating α-D- mannopyranosylphosphate transferase. Chem. Eur. J. 11, 2019-2030 (2005)
35. Liu, X.Y., Siegrist, S., Amacker, M., Zurbriggen, R., Pluschke, G., Seeberger, P.H.: Enhancement of the immunogenicity of synthetic carbohydrates by conjugation to virosomes: a Leishmaniasis vaccine candidate. ACS Chem. Bio. 1, 161-164 (2006)
36. Hotha, S., Kashyap, S.: Propargyl glycosides as stable glycosyl donors: anomeric activation and glycoside syntheses. J. Am. Chem. Soc. 128, 9620-9621 (2006)
37. Hotha, S., Kashyap, S.: Stereoselective synthesis of α-glucosides from 3-O-propargyl protected glucal exploiting the alkynophilicity of AuCl3. Tetrahedron Lett. 47, 2021-2023 (2006)
38. Sureshkumar, G., Hotha, S.: Propargyl 1,2-orthoesters as glycosyl donors: stereoselective synthesis of 1,2-trans glycosides and disaccharides. Tetrahedron Lett. 48, 6564-6568 (2007)
39. Kashyap, S., Vidadala, S.R., Hotha, S.: Synthesis of C-2 methylene glycosides from C-2 propargyloxymethyl glycals exploiting the alkynophilicity of AuCl3. Tetrahedron Lett. 48, 8960-8962 (2007)
40. Sureshkumar, G., Hotha, S.: Gold mediated glycosylations: selective activation of propargyl 1,2-orthoesters in the presence of aglycones containing a propargyl moiety Chem. Commun. 4282-4284 (2008)
41. Vidadala, S.R., Hotha, S.: Methyl glycosides are identified as glycosyl donors for the synthesis of glycosides, disaccharides and oligosaccharides Chem. Commun. 2505-2507 (2009)
42. Vidadala, S.R., Thadke, S.A., Hotha, S.: Orthogonal activation of propargyl and n-pentenyl glycosides and 1,2-orthoesters. J. Org. Chem. 74, 9233-9236 (2009)
43. Kayastha, A.K., Hotha, S.: Gold-catalyzed glycosidations: unusual cleavage of the interglycosidic bond while studying the armed/ disarmed effect of propargyl glycosides. Tetrahedron Lett. 51, 5269-5272 (2010)
44. Thadke, S.A., Hotha, S.: Gold-catalyzed glycosidations: synthesis of 1,6-anhydro saccharides. Tetrahedron Lett 51, 5912-5914 (2010). Other papers on gold catalyzed glycosidations
45. Li, Y., Yang, Y., Yu, B.: An efficient glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors under the catalysis of Ph3PAuOTf. Tetrahedron Lett. 49, 3604-3608 (2008)
46. Li, Y., Tank, P., Chen, Y., Yu, B.: Gold(I)-catalyzed glycosidation of 1,2-anhydrosugars. J. Org. Chem. 73, 4323-4325 (2008)
47. Götze, S., Fitzner, R., Kunz, H.: Gold catalysis in glycosylation reactions. Synlett 3346-3348 (2009)
48. Mamidyala, S.K., Finn, M.G.: Glycosylation using unprotected alkynyl donors. J. Org. Chem. 74, 8417-8420 (2009)
49. Kartha, K.P.R., Jennings, H.J.: A simplified, one-pot preparation of acetobromosugars from reducing sugars. J. Carbohydr. Chem. 9, 777-781 (1990)
50. Larsen, K., Olsen, C.E., Motawia, M.S.: A facile protocol for direct conversion of unprotected sugars into phenyl 4,6-O-benzylidene-per- O-acetylated-1,2-trans-thioglycosides. Carbohydr. Res. 338, 199-202 (2003)
51. Hunsen, M., Long, D.A., D'Ardenne, C.R., Smith, A.L.: Mild onepot preparation of glycosyl bromides. Carbohydr. Res. 340, 2670-2674 (2005)
52. Mach, M., Schlueter, U., Mathew, F., Fraser-Reid, B., Hazan, K.C.: Comparing n-pentenyl orthoesters and n-pentenyl glycosides as alternative glycosyl donors. Tetrahedron 58, 7345-7354 (2002)
53. Warren, C.D., Augé, C., Laver, M.L., Suzuki, S., Power, D., Jeanloz, R.W.: The synthesis of O-β-D-mannopyranosyl-(1→4)- O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido- 2-deoxy-D-glucopyranose. Carbohydrate Res. 82, 71-83 (1980)
54. Liu, K.K.-C., Danishefsky, S.J.: Route from glycals to mannose β-glycosides. J. Org. Chem 59, 1892-1894 (1994)