Pre-activation-based one-pot synthesis of an α-(2,3)-sialylated core-fucosylated complex type bi-antennary N-glycan dodecasaccharide

Chemistry - A European Journal

Volumn 14, Issue 23, 2008, Pages 7072-7081

  Sun, Bin ^a,b   Srinivasan, Balasubramanian ^a   Huang, Xuefei ^a,b  

^a UNIVERSITY OF TOLEDO   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Carbohydrates; Glycosylation; N glycans; Synthesis design

Indexed keywords

POLYSACCHARIDES;

CARBOHYDRATES; GLYCOSYLATION; N-GLYCANS; SYNTHESIS DESIGN;

COMPLEXATION;

FUCOSE; POLYSACCHARIDE; SIALIC ACID DERIVATIVE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMISTRY; MOLECULAR GENETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

CARBOHYDRATE SEQUENCE; FUCOSE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; POLYSACCHARIDES; SIALIC ACIDS;

EID: 53849145029     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800757     Document Type: Article

References (79)

1. R. A. Dwek. Chem. Rev. 1996, 96, 683-720.
2. S. André, T. Ko ár, R. Schuberth, C. Unverzagt, S. Kojima, H.-J. Gabius, Biochemistry 2007, 46, 6984-6995, and references therein.
3. K. Shinya, M. Ebina, S. Yamada, M. Ono, N. Kasai, Y. Kawaoka, Nature 2006, 440, 435-436.
4. T. Shinkawa, K. Nakamura, N. Yamane, E. Shoji-Hosaka, Y. Kanda, M. Sakurada, K. Uchida, H. Anazawa, M. Saloh, M. Yamasaki, N. Hanai, K. Shitara, J. Biol. Chem. 2003, 278, 3466-3473.
5. Compound 1 has been characterized within an N-glycan mixture isolated from carbohydrates attached to human γ-interferon, see: J. H. G. M. Mutsaers, J. P. Kamerling, R. Devos, Y. Guisez, W. Fiers, J. F. G. Vilegenlhart, Eur. J. Bioehem. 1986, 156, 651-654.
6. P. J. Johnson, T. C. W. Poon, N. M. Hjelm, C. S. Ho, S. K. W. Ho, C. Welby, D. Stevenson, T. Patel, R. Parekh, R. R. Townsend, Br. J. Can. 1999, 81, 1188-1195.
7. K. Taketa, Electrophoresis 1998, 19, 2595-2602.
8. M. Tajiri, C. Ohyama, Y. Wada, Glycobiology 2008, 18, 2-8.
9. F.-T. A. Chen, R. A. Evangelista, Electrophoresis 1998, 19, 2639-2644.
10. E. Watson, A. Bhide, H. van Halbeek, Glycobiology 1994, 4, 227-237.
11. G. Chen, Q. Wan, Z. Tan, C. Kan, Z. Hua, K. Ranganathan, S. J. Danishefsky, Angew. Chem. 2007, 119, 7527-7531;
12. Angew. Chem. Int. Ed. 2007, 46, 7383-7387. and references therein.
13. C. Unverzagt, S. Eller, S. Mezzato, R. Schuberth, Chem. Eur. J. 2008, 14, 1304-1311. and references therein.
14. Nakano, A. Ishiwata, H. Ohta, Y. Ito, Carbohydr. Res. 2007, 342, 675-695, and references therein.
15. S. Jonke, K. Liu, R. R. Schmidt, Chem. Eur. J. 2006, 12, 1274-1290.
16. T. W. D. F. Rising, T. D. W. Claridge, N. Davies, D. P. Gamblin, J. W. B. Moir, A. J. Fairbanks, Carbohydr. Res. 2006, 341, 1574-1596.
17. B. Li, Y. Zeng, S. Hauser, H. Song, L. Wang, J. Am. Chem. Soc. 2005, 127, 9692-9693.
18. V. Y. Dudkin, J. S. Miller, S. J. Danishefsky, J. Am. Chem. Soc. 2004, 126, 736-738.
19. G. M. Watt, G. J. Boons, Carbohydr. Res. 2004, 339, 181-193.
20. D. M. Ratner, E. R. Swanson, P. H. Seeberger, Org. Lett. 2003, 5, 4717-4720.
21. V. Y. Dudkin, D. Crich, Tetrahedron Lett. 2003, 44, 1787-1789.
22. For a chemoenzymatic synthesis of compound 1. see: C. Unverzagt, S. André, J. Seifert, S. Kojima, C. Fink, G. Srikrishna, H. Freeze, K. Kayser, H.-J. Gabius, J. Med. Chem. 2002, 45, 478-491.
23. J. Seifert, M. Lergenmüller, Y. Ito, Angew. Chem. 2000, 112, 541-544;
24. Angew. Chem. Int. Ed. 2000, 39, 531-534.
25. A. Düffels, S. V. Ley, J. Chem. Soc. Perkin Trans. 1 1999, 375-378.
26. B. Wu, Z. Hua, D. Warren, K. Ranganathan, Q. Wan, G. Chen, Z. Tan, J. Chen, A. Endoa, S. J. Danishefsky, Tetrahedron Lett. 2006, 47, 5577-5579.
27. P. J. Garegg, Adv. Carbohydr. Chem. Bioehem. 1997, 52, 179-205.
28. N. Teumelsan, X. Huang, J. Org. Chem. 2007, 72, 8976-8979.
29. A. Dan, M. Lergenmüller, M. Amano, Y. Nakahara, T. Ogawa, Y. Ito, Chem. Eur. J. 1998, 4, 2182-2190.
30. N. Shao, Z. Guo, Pol. J. Chem. 2005, 79, 297-307.
31. W. Gunther, H. Kunz, Angew. Chem. 1990, 102, 1068;
32. Angew. Chem. Int. Ed. Engl. 1990, 29, 1050.
33. E. Attolino, T. W. D. F. Rising, C. D. Heidecke, A. J. Fairbanks, Tetrahedron: Asymmetry 2007, 18, 1721-1734.
34. G. Stork, J. J. La Clair, J. Am. Chem. Soc. 1996, 118, 247-248.
35. Z. Guo, Y. Nakahara, Y. Nakahara, T. Ogawa, Bioorg. Med. Chem. 1997, 5, 1917-1924, and references therein.
36. D. Crich, A. Banerjee, Q. Yao, J. Am. Chem. Soc. 2004, 126, 14930-14934, and references therein.
37. D. Crich, H. Li, Q. Yao, D. J. Wink, R. D. Sommer, A. L. Rheingold, J. Am. Chem. Soc. 2001, 123, 5826-5828.
38. D. Crich, S. Sun, Tetrahedron 1998, 54, 8321-8348.
39. D. Crich, W. Li, H. Li. J. Am. Chem. Soc. 2004, 126, 15081-15086.
40. T. Ogawa, S. Nakabayashi, Carbohydr. Res. 1981, 97, 81-86.
41. Regioselectivity of this glycosylation was confirmed by NMR analysis of compound 3, prepared from a separation reaction following the identical procedure.
42. A. Miermont, Y. Zeng, Y. Jing, X.-S. Ye, X. Huang, J. Org. Chem. 2007, 72, 8958-8961.
43. U. Ellervik, G. Magnusson, J. Org. Chem. 1998, 63, 9314-9322.
44. Z. Zhang, K. Niikura, X. Huang, C.-H. Wong. Can. J. Chem. 2002, 80, 1051-1054.
45. H. J. Vermeer, C. M. Van Dijk, J. P. Kamerling. J. F. G. Vliegenthart, Eur. J. Org. Chem. 2001, 193-203, and references therein.
46. R. U. Lemieux, K. B. Hendricks, R. V. Stick, K. James, J. Am. Chem. Soc. 1975, 97, 4056-4062.
47. X. Huang, L. Huang, H. Wang, X.-S. Ye, Angew. Chem. 2004, 116, 5333-5336;
48. Angew. Chem. Int. Ed. 2004, 43, 5221-5224.
49. V. Martichonok, G. M. Whitesides, J. Org. Chem. 1996, 61, 1702-1706.
50. L. Huang, Z. Wang, X. Li, X.-S. Ye, X. Huang, Carbohydr. Res. 2006, 341, 1669-1679.
51. K. Bock, C. Pedersen, J. Chem. Soc. Perkin Trans. 2 1974, 293-297.
52. M. Sakagami, H. Hamana, Tetrahedron Lett. 2000, 41, 5547-5551.
53. V. Y. Dudkin, J. S. Miller, S. J. Danishefsky, Tetrahedron Lett. 2003, 44, 1791-1793.
54. W. Wang, F. Kong, Angew. Chem. 1999, 111, 1330-1333;
55. Angew. Chem. Int. Ed. 1999, 38, 1247-1250.
56. G. J. Boons, A. Demchenko, Chem. Rev. 2000, 100, 4539-4565.
57. H. Tanaka, M. Adachi, T. Takahashi, Chem. Eur. J. 2005, 11, 849-862.
58. H. Ando, Y. Koike, S. Koizumi, H. Ishida, M. Kiso, Angew. Chem. 2005, 117, 6917-6921;
59. Angew. Chem. Int. Ed. 2005, 44, 6759-6763.
60. J. Xia, J. L. Alderfer, C. F. Piskorz, K. L. Matta. Chem. Eur. J. 2000, 6, 3442-3451.
61. C. De Meo, A. Demchenko, G. J. Boons, J. Org. Chem. 2001, 66, 5490-5497.
62. D. Crich, W. Li, Org. Lett. 2006, 8, 959-962.
63. C.-S. Yu, K. Niikura, C.-C. Lin, C.-H. Wong, Angew. Chem. 2001, 113, 2984-2987;
64. Angew. Chem. Int. Ed. 2001, 40, 2900-2903.
65. K. Tanaka, T. Goi, K. Fukase, Synlett 2003, 2958-2962.
66. D. Crich, B. Wu, Tetrahedron 2008, 64, 2042-2047, and references therein.
67. M. D. Farris, C. De Meo, Tetrahedron Lett. 2007, 48, 1225-1227.
68. H. Tanaka, Y. Nishiura, T. Takahashi, J. Am. Chem. Soc. 2006, 128, 7124-7125.
69. T. J. Donohoe, J. G. Logan, D. D. P. Laffan, Org. Lett. 2003, 5, 4995-4998.
70. A. A. Sherman, O. N. Yudina, Y. V. Mironov, V. Sukhova, A. S. Shashkov, V. M. Menshov, N. E. Nifantieva, Carbohydr. Res. 2001, 336, 13-46.
71. F. Bélot, J.-C. Jacquinet, Carbohydr. Res. 2000, 325, 93-106.
72. S. Hanashima, B. Castagner, D. Esposito, T. Nokami, P. H. Seeberger, Org. Lett. 2007, 9, 1777-1779.
73. S. Cai, B. Yu, Org. Lett. 2003, 5, 3827-3830.
74. X.-S. Ye, X. Huang, C.-H. Wong, Chem. Commun. 2001, 974-975.
75. L. Huang, X. Huang, Chem. Eur. J. 2007, 13, 529-540.
76. Z. Wang, L. Zhou, K. El-boubbou, X.-S. Ye, X. Huang, J. Org. Chem. 2007, 72, 6409-6420.
77. K. C. Nicolaou, C. W. Hummel, Y. Iwabuchi, J. Am. Chem. Soc. 1992, 114, 3126-3128.
78. I. Cumpstey, K. Chayajarus, A. J. Fairbanks, A. J. Redgrave, C. M. P. Seward, Tetrahedron: Asymmetry 2004, 15, 3207-3221.
79. C.-C. Lin, K.-T. Huang, C.-C. Lin, Org. Lett. 2005, 7, 4169-4172.