A new one-pot synthesis of α-Gal epitope derivatives involved in the hyperacute rejection response in xenotransplantation

Tetrahedron

Volumn 61, Issue 17, 2005, Pages 4313-4321

  Wang, Yuhang ^a   Yan, Qingyan ^a   Wu, Jingping ^a   Zhang, Li He ^a   Ye, Xin Shan ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

Glycosylations; Oligosaccharides; One pot synthesis; Xenotransplantation; Galactosyl epitopes

Indexed keywords

(3 BENZYL 3 BENZYLOXYCARBONYLAMINO)PROPYL 2,3,6 TRI O BENZYL 4 O [2 O BENZOYL 3 O (2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL) 4,6 O BENZYLIDINE BETA DEXTRO GALACTOPYRANOSYL] BETA DEXTRO GLUCOPYRANOSIDE; (3 BENZYLOXYCARBONYLAMINO)PROPYL 3,6 DI O BENZYL 4 O [2 O BENZOYL 3 O (2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL) 4,6 O BENZYLIDENE BETA DEXTRO GALACTOPYRANOSYL] 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSIDE; 3 AMINOPROPYL 4 O [3 O (ALPHA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO GALACTOPYRANOSYL] 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSIDE; 3 AMINOPROPYL 4 O [3 O (ALPHA DEXTRO GALACTOPYRANOSYL) BETA DEXTRO GALACTOPYRANOSYL] BETA DEXTRO GLUCOPYRANOSIDE; EPITOPE; GALACTOSE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HYPERACUTE GRAFT REJECTION; PRIORITY JOURNAL; PROTECTION; XENOTRANSPLANTATION;

SUS SCROFA;

EID: 16244402312     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.023     Document Type: Article

References (47)

1. J.P. Fryer, J.R. Leventhal, and A.J. Matas Transplant. Immunol. 3 1995 21 31
2. M.S. Sandrin, and I.FC. McKenzie Curr. Opin. Immunol. 11 1999 527 531
3. T.E. Mollnes, and A.E. Fiane Mol. Immunol. 36 1999 269 276
4. M. Cascalho, and J.L. Platt Nat. Rev. Immunol. 1 2001 154 160
5. U. Galili, E.A. Rachmilewitz, A. Peleg, and I. Flechner J. Exp. Med. 160 1984 1519 1531
6. U. Galili, M.R. Clark, S.B. Shohet, J. Buehler, and B.A. Mancher Proc. Natl. Acad. Sci. U. S. A. 84 1987 1369 1373
7. U. Galili, S.B. Shohet, E. Kobrin, C.L.M. Stults, and B.A. Mancher J. Biol. Chem. 263 1988 17755 17762
8. U. Galili, R.E. Mandrell, R.M. Hamadeh, S.B. Shohet, and J.M. Griffis Infect. Immun. 56 1988 1730 1737
9. J.L. Platt, G.M. Vercellotti, and A.P. Dalmasso Immunol. Today 11 1990 456 457
10. C. Robert, and J.L. Platt J. Hepatol. 25 1996 248 258
11. U. Galili, B.A. Mancher, J. Buehler, and S.B. Shohet J. Exp. Med. 162 1985 573 582
12. D.K. Cooper Clin. Transplant. 6 1992 178 183
13. A.H. Good, D.K. Cooper, A.J. Malcolm, R.M. Ippolito, E. Koren, F.A. Neethling, Y. Ye, N. Zuhdi, and L.R. Lamontagne Transplant. Proc. 24 1992 559 562
14. D.K. Cooper, E. Koren, and R. Oriol Immunol. Rev. 141 1994 31 58
15. E.C. Hallberg, V. Strokan, T.D.H. Cairns, M.E. Breimer, and B.E. Samuelsson Xenotransplantation 5 1998 246 256
16. S. Li, F. Neethling, S. Taniguchi, J.-C. Yeh, T. Kobayashi, Y. Ye, E. Koren, R.D. Cummings, and D.K. Cooper Transplantation 62 9 1996 1324 1331
17. P.M. Simon, F.A. Neethling, S. Taniguchi, P.L. Goode, D. Zopf, W.W. Hancock, and D.K. Cooper Transplantation 65 3 1998 346 353
18. Y. Chen, W. Zhang, X. Chen, J. Wang, and P.G. Wang J. Chem. Soc., Perkin Trans. 1 2001 1716 1722
19. K.P. Naicker, H. Li, A. Heredia, H. Song, and L.-X. Wang Org. Biomol. Chem. 2 2004 660 664
20. J. Fang, J. Li, X. Chen, Y. Zhang, J. Wang, Z. Guo, W. Zhang, L. Yu, K. Brew, and P.G. Wang J. Am. Chem. Soc. 104 1998 6635 6641
21. W. Zhang, J. Wang, J. Li, and L. Yu J. Carbohydr. Res. 18 1999 1009 1017
22. J.W. Fang, X. Chen, W. Zhang, A. Janczuk, and P.G. Wang Carbohydr. Res. 329 2000 873 878
23. T. Zhu, and G.J. Boons J. Chem. Soc., Perkin Trans. 1 1998 857 860
24. C. Gege, W. Kinzy, and R.R. Schmidt Carbohydr. Res. 328 2000 459 466
25. Z. Zhang, I.R. Ollmann, X.-S. Ye, R. Wischnat, T. Baasov, and C.-H. Wong J. Am. Chem. Soc. 121 1999 734 753
26. X.-S. Ye, and C.-H. Wong J. Org. Chem. 65 2000 2410 2431
27. K.M. Koeller, and C.-H. Wong Chem. Rev. 100 2000 4465 4493
28. S.V. Ley, and H.W.M. Priepke Angew. Chem. Int. Ed. Engl. 33 1994 2292 2294
29. N.L. Douglas, S.V. Ley, U. Lucking, and S.L. Warriner J. Chem. Soc., Perkin Trans. 1 1998 51 65
30. P. Grice, S.V. Ley, J. Pietruszka, and H.W.M. Priepke Angew. Chem. Int. Ed. 35 1996 197 200
31. S. Raghaven, and D. Kahne J. Am. Chem. Soc. 115 1993 1580 1581
32. H. Yamada, T. Harada, and T. Takahashi J. Am. Chem. Soc. 116 1994 7919 7920
33. R. Geurtsen, D.S. Holmes, and G.-J. Boons J. Org. Chem. 62 1997 8145 8154
34. S.-F. Lu, Q. O'yang, Z.-W. Guo, B. Yu, and Y.-Z. Hui J. Org. Chem. 62 1997 8400 8405
35. J.-Q. Wang, X. Chen, W. Zhang, S. Zacharek, Y. Chen, and P.G. Wang J. Am. Chem. Soc. 121 1999 8174 8181
36. J. Liaigre, D. Dubreuil, J.-P. Pradere, and J.-F. Bouhours Carbohydr. Res. 325 2000 265 277
37. M. Dubber, and T.K. Lindhorst J. Org. Chem. 65 2000 5275 5281
38. B. Liu, and R. Roy J. Chem. Soc., Perkin Trans. 1 2001 773 779
39. G.W. Byrne, A. Schwarz, J.R. Fesi, P. Birch, A. Nepomich, I. Bakaj, M.A. Velardo, C. Jiang, A. Manzi, H. Dintzis, L.E. Diamond, and J.S. Logan Bioconjugate Chem. 13 2002 571 581
40. P. Fügedi, and P.J. Garegg Carbohydr. Res. 149 1986 c9 c12
41. P. Konradsson, U.E. Udodong, and B. Fraser-Reid Tetrahedron Lett. 31 1990 4313 4316
42. V. Martichonok, and G.M. Whitesides J. Org. Chem. 61 1996 1702 1706
43. D. Crich, and S. Sun Tetrahedron 54 1998 8321 8348
44. D. Crich, and M. Smith J. Am. Chem. Soc. 123 2001 9015 9020
45. T.K.-K. Mong, H.-K. Lee, S.G. Duron, and C.-H. Wong Proc. Natl. Acad. Sci. U. S. A. 100 2003 797 802
46. J.D.C. Codee, L.J. van den Bos, R.E.J.N. Litjens, H.S. Overkleeft, C.A.A. van Boeckel, J.H. van Boom, and G.A. van der Marel Tetrahedron 60 2004 1057 1064
47. Y. Wang, X. Huang, L.-H. Zhang, and X.-S. Ye Org. Lett. 6 2004 4415 4417