Synthesis of glycosaminoglycan oligosaccharides. Part 5: Synthesis of a putative heparan sulfate tetrasaccharide antigen involved in prion diseases

Tetrahedron

Volumn 66, Issue 40, 2010, Pages 8036-8046

  Daragics, Katalin ^a   Fügedi, Péter ^a  

^a CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

Glycosylation; Heparan sulfate; N Acetyl d glucosamine; Oligosaccharide synthesis; Prion diseases; Thioglycosides

Indexed keywords

ETHYL 2 O BENZOYL 3 O BENZYL 4 O(1 NAPHTHYL)METHYL 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; ETHYL 2 O BENZOYL 3 O BENZYL 4,6 O BENZYLIDENE 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; ETHYL 2 O BENZOYL 3 O BENZYL 4,6 O(1 NAPHTHYL)METHYLENE 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; ETHYL 2 O BENZOYL 3 O BENZYL 6 O CHLOROACETYL 4 O(1 NAPHTHYL)METHYL 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; ETHYL 2 O BENZOYL 3,4 DI O BENZYL 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; ETHYL 3 O BENZYL 4,6 O(1 NAPHTHYL)METHYLENE 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; GLUCOPYRANOSIDE; GLUCOSAMINE DERIVATIVE; GLUCURONIC ACID; GLYCOSAMINOGLYCAN; HEPARAN SULFATE; METHYL(2 BENZOYL 3 O BENZYL 6 O CHLOROACETYL BETA DEXTRO GLUCOPYRANOSYL) (1-4) (2 ACETAMIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE); METHYL[(BETA DEXTRO GLUCOPYRANOSYL)URONIC ACID] (1-4) (2 AMINO 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSYL) (1-4) [(BETA DEXTRO GLUCOPYRANOSYL)URONIC ACID] (1-4) (2 ACETAMIDO 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE); METHYL[2 O BENZOYL 3 O BENZYL 4 O(1 NAPHTHYL)METHYL BETA DEXTRO GLUCOPYRANOSYL] (1-4) (2 ACETAMIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE); METHYL[2 O BENZOYL 3 O BENZYL 6 O CHLOROACETYL 4 O(1 NAPHTHYL)METHYL BETA DEXTRO GLUCOPYRANOSYL] (1-4) (2 ACETAMIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE); METHYL[TERT BUTYL(2 O BENZOYL 3 O BENZYL BETA DEXTRO GLUCOPYRANOSYL)URONATE] (1-4) (2 ACETAMIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE); METHYL[TERT BUTYL[2 O BENZOYL 3 O BENZYL 4 O(1 NAPHTHYL)METHYL BETA DEXTRO GLUCOPYRANOSYL]URONATE] (1-4) (2 ACETAMIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE); PHENYL[TERT BUTYL(2 O BENZOYL 3,4 DI O BENZYL BETA DEXTRO GLUCOPYRANOSYL)URONATE] (1-4) (2 AZIDO 3,6 DI O BENZYL 2 DEOXY 1 THIO BETA DEXTRO GLUCOPYRANOSIDE); TERT BUTYL(2 O BENZOYL 3,4 DI O BENZYL 1 O TRICHLOROACETIMIDOYL ALPHA DEXTRO GLUCOPYRANOSE)URONATE; TERT BUTYL(ETHYL 3,4 DI O BENZYL 2 O BENZOYL 1 THIO BETA DEXTRO GLUCOPYRANOSIDE)URONATE; TETRASACCHARIDE; THIOGLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; GLYCOSYLATION; PRION DISEASE; PRIORITY JOURNAL; SYNTHESIS;

EID: 77956394384     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.08.004     Document Type: Article

References (69)

1. D.A. Lane, and U. Lindahl Heparin. Chemical and Biological Properties, Clinical Applications 1989 CRC Boca Raton, Florida, USA
2. L. Kjellén, and U. Lindahl Annu. Rev. Biochem. 60 1991 443 475
3. B. Casu, and U. Lindahl Adv. Carbohydr. Chem. Biochem. 57 2001 159 206
4. H.G. Garg, R.J. Linhardt, and C.A. Hales Chemistry and Biology of Heparin and Heparan Sulfate 2005 Elsevier Amsterdam, The Netherlands
5. E.H. Conrad Heparin-Binding Proteins 1998 Academic San Diego, CA, USA
6. I. Capila, and R.J. Linhardt Angew. Chem., Int. Ed. 41 2002 390 412
7. P. Fügedi Mini-Rev. Med. Chem. 3 2003 659 667
8. A.D. Snow, and T.N. Wight Neurobiol. Aging 10 1989 481 497
9. A.D. Snow, and G.M. Castillo Amyloid-Int. J. Exp. Clin. Investig. 4 1997 135 141
10. J. Diaz-Nido, F. Wandosell, and J. Avila Peptides 23 2002 1323 1332
11. T. Mayer-Sonnenfeld, M. Zeigler, M. Halimi, Y. Dayan, C. Herzog, C.I. Lasmezas, and R. Gabizon Neurobiol. Dis. 20 2005 738 743
12. N. Hijazi, Z. Kariv-Inbal, M. Gasset, and R. Gabizon J. Biol. Chem. 280 2005 17057 17061
13. S.B. Prusiner Science 216 1982 136 144
14. M. Mehrpour, and P. Codogno Cancer Lett. 290 2010 1 23
15. J.H. Su, B.J. Cummings, and C.W. Cotman Neuroscience 51 1992 801 813
16. C. Leteux, W. Chai, K. Nagai, C.G. Herbert, A.M. Lawson, and T. Feizi J. Biol. Chem. 276 2001 12539 12545
17. J. Tatai, G. Osztrovszky, M. Kajtár-Peredy, and P. Fügedi Carbohydr. Res. 343 2008 596 606
18. J. Tatai, and P. Fügedi Tetrahedron 64 2008 9865 9873
19. Z. Csíki, and P. Fügedi Tetrahedron Lett. 51 2010 391 395
20. Z. Csíki, and P. Fügedi Tetrahedron 66 2010 7821 7837
21. Daragics, K.; Fügedi, P. 14th European Carbohydrate Symposium, Lübeck, Germany, 2007, Abstract PO-050.
22. D. Hamza, R. Lucas, T. Feizi, W. Chai, D. Bonnaffé, and A. Lubineau ChemBioChem 7 2006 1856 1858
23. P. Bindschädler, C. Noti, E. Castagnetti, and P.H. Seeberger Helv. Chim. Acta 89 2006 2591 2610
24. M. Petitou, P. Duchaussoy, I. Lederman, J. Choay, J.-C. Jacquinet, P. Sinaÿ, and G. Torri Carbohydr. Res. 167 1987 67 75
25. C.A.A. van Boeckel, and M. Petitou Angew. Chem., Int. Ed. Engl. 32 1993 1671 1690
26. J.-L. de Paz, R. Ojeda, N. Reichardt, and M. Martin-Lomas Eur. J. Org. Chem. 2003 3308 3324
27. J.L. de Paz, and M. Martin-Lomas Eur. J. Org. Chem. 2005 1849 1858
28. G.J.S. Lohman, and P.H. Seeberger J. Org. Chem. 69 2004 4081 4093
29. For a recent paper attempting to find a solution to this problem, see: P. Bindschädler, L.O. Dialer, and P.H. Seeberger J. Carbohydr. Chem. 28 2009 395 420
30. H. Paulsen Angew. Chem., Int. Ed. Engl. 21 1982 155 173
31. D. Crich, and V. Dudkin J. Am. Chem. Soc. 123 2001 6819 6825
32. L. Liao, and F.-I. Auzanneau Org. Lett. 5 2003 2607 2610
33. L. Liao, and F.-I. Auzanneau J. Org. Chem. 70 2005 6265 6273
34. J.L. Hendel, A. Cheng, and F.-I. Auzanneau Carbohydr. Res. 343 2008 2914 2923
35. J. Tamura, Y. Nakada, K. Taniguchi, and M. Yamane Carbohydr. Res. 343 2008 39 47
36. R. Lucas, D. Hamza, A. Lubineau, and D. Bonnaffé Eur. J. Org. Chem. 2004 2107 2117
37. P.J. Garegg, L. Olsson, and S. Oscarson J. Org. Chem. 60 1995 2200 2204
38. C. Krog-Jensen, and S. Oscarson Carbohydr. Res. 308 1998 287 296
39. A.V. Stachulski, and G.N. Jenkins Nat. Prod. Rep. 15 1998 173 186
40. For some recent examples of problematic glycosylations with D-glucuronic acid donors, see: (i) Failure of glycoside formation:
41. J. Madaj, A. Trynda, M. Jankowska, and A. Wisniewski Carbohydr. Res. 337 2002 1495 1498
42. W. Zhao, and F. Kong Carbohydr. Res. 339 2004 1779 1786
43. S.M. Rele, S.S. Iyer, S. Baskaran, and E.L. Chaikof J. Org. Chem. 69 2004 9159 9170
44. A. O'Brien, C. Lynch, K.M. O'Boyle, and P.V. Murphy Carbohydr. Res. 339 2004 2343 2354
45. W. Zhao, and F. Kong Carbohydr. Res. 340 2005 1673 1681
46. (ii) Orthoester formation: Ref. 19e:
47. J. Tamura, K.W. Neumann, and T. Ogawa Liebigs Ann. 1996 1239 1257
48. E. Kaji, and N. Harita Tetrahedron Lett. 41 2000 53 56
49. X.-A. Lu, C.-H. Chou, C.-C. Wang, and S.-C. Hung Synlett 2003 1364 1366
50. (iii) Formation of acylated acceptor: Ref. 19a,b.;
51. A.V. Stachulski Tetrahedron Lett. 42 2001 6611 6613
52. (iv) Formation of other types of products:
53. A.G. Pearson, M.J. Kiefel, V. Ferro, and M. von Itzstein Carbohydr. Res. 340 2005 2077 2085
54. H. Ochiai, M. Ohmae, and S. Kobayashi Carbohydr. Res. 339 2004 2769 2788
55. H.A. Orgueira, A. Bartolozzi, P. Schell, and P.H. Seeberger Angew. Chem., Int. Ed. 41 2002 2128 2131
56. H.A. Orgueira, A. Bartolozzi, P. Schell, R.E.J.N. Litjens, E.R. Palmacci, and P.H. Seeberger Chem. - Eur. J. 9 2003 140 169
57. P. Fügedi, and P.J. Garegg Carbohydr. Res. 149 1986 C9 C12
58. P.J. Garegg, I. Kvarnström, A. Niklasson, G. Niklasson, and S.C. Svensson J. Carbohydr. Chem. 12 1993 933 953
59. T. Ziegler, E. Eckhardt, and V. Birault J. Org. Chem. 58 1993 1090 1099
60. K. Daragics, and P. Fügedi Tetrahedron Lett. 50 2009 2914 2916
61. E.J. Corey, and B. Samuelsson J. Org. Chem. 49 1984 4735-4735
62. M. Nilsson, C.-M. Svahn, and J. Westman Carbohydr. Res. 246 1993 161 172
63. S.S. Rana, J.J. Barlow, and K.L. Matta Carbohydr. Res. 113 1983 257 271
64. M. Martin-Lomas, M. Flores-Mosquera, and J.L. Chiara Eur. J. Org. Chem. 2000 1547 1562
65. J. Tatai, and P. Fügedi Org. Lett. 9 2007 4647 4650
66. H. Lönn Carbohydr. Res. 139 1985 105 113
67. C.A.A. van Boeckel, and T. Beetz Tetrahedron Lett. 24 1983 3775 3778
68. Monosaccharide units of the tetrasaccharide are denoted by the letters a-d, starting from the reducing end.
69. K. Zegelaar-Jaarsveld, S.A.W. Smits, G.A. van der Marel, and J.H. van Boom Bioorg. Med. Chem. 4 1996 1819 1832