Synthesis of a C3-symmetric (1→6)-N-acetyl-β-D- glucosamine octadecasaccharide using click chemistry

Carbohydrate Research

Volumn 340, Issue 16, 2005, Pages 2476-2482

  Chen, Qi ^a   Yang, Feng ^a   Du, Yuguo ^a  

^a RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

Author keywords

Antitumor activity; Click chemistry; Glucosamine; Glycosylation; Thioglycosides

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; OLIGOMERS; POLYSACCHARIDES; TUMORS;

ANTITUMOR ACTIVITY; CLICK CHEMISTRY; CYCLOADDITION; GLUCOSAMINE; THIOGLYCOSIDES;

BIOSYNTHESIS;

CISPLATIN; GLUCOSAMINE DERIVATIVE; LENTINAN; OLIGOSACCHARIDE; ALKYNE; ANTINEOPLASTIC AGENT; AZIDE; COPPER; GLUCOSAMINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBOHYDRATE SYNTHESIS; CATALYSIS; CONTROLLED STUDY; CYCLOADDITION; DRUG SCREENING; DRUG SYNTHESIS; MOUSE; NONHUMAN; PRIORITY JOURNAL; ANIMAL; CARBOHYDRATE ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; METABOLISM; MOLECULAR GENETICS; SYNTHESIS; TUMOR CELL LINE;

ALKYNES; ANIMALS; ANTINEOPLASTIC AGENTS; AZIDES; CARBOHYDRATE SEQUENCE; CATALYSIS; CELL LINE, TUMOR; COPPER; DRUG SCREENING ASSAYS, ANTITUMOR; GLUCOSAMINE; HUMANS; MICE; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; OLIGOSACCHARIDES;

EID: 26844521719     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2005.08.013     Document Type: Article

References (31)

1. R.A. Dwek Chem. Rev. 96 1996 683 720
2. K.M. Koeller, and C.H. Wong Nat. Biotechnol. 18 2000 835 841
3. A. Varki R. Cummings J. Esko H. Freeze G. Hart J. Marth Essentials of Glycobiology 1999 Cold Spring Harbor Laborotary Press New York
4. S.D. Rosen, and C.R. Bertozzi Curr. Biol. 6 1996 261 264
5. S. Vaulont, and A. Kahn FASEB J. 8 1994 28 35
6. Y.C. Lee, and Y.T. Lee Acc. Chem. Res. 28 1995 321 327
7. N.V. Bovin, and H.J. Gabius Chem. Soc. Rev. 24 1995 413 422
8. R. Roy Curr. Opin. Struct. Biol. 6 1996 692 702
9. J.J. Lundquist, and E.J. Toone Chem. Rev. 102 2002 555 578
10. E.J. Goedo, W.J. Sanders, and L.L. Kiessling Nature 392 1998 30 31
11. Y. Nishida, H. Dohi, and K. Kobayashi Tetrahedron Lett. 39 1998 8681 8684
12. K. Matsuoka, M. Terabatake, Y. Esumi, D. Terunuma, and H. Kuzuhara Tetrahedron Lett. 40 1999 7839 7842
13. P.I. Kitov, J.M. Sadawska, G. Mulvey, G.D. Armstrong, H. Ling, N.S. Pannu, W.J. Read, and D.R. Bundle Nature 403 2000 669 672
14. T. Toyokuni, B. Dean, S. Cai, D. Boivin, S. Kakomori, and A.K. Singhal J. Am. Chem. Soc. 116 1994 395 396
15. H.C. Hansen, S. Haataja, J. Finne, and G. Magnusson J. Am. Chem. Soc. 119 1997 6974 6979
16. F. Yang, and Y. Du Carbohydr. Res. 338 2003 495 502
17. F. Yang, H. He, and Y. Du Tetrahedron Lett. 43 2002 7561 7563
18. F. Yang, Y. Hua, and Y. Du Carbohydr. Res. 338 2003 1313 1318
19. Yang, F., Ph. D. thesis, Graduate School of Chinese Academy of Sciences, 2003.
20. F. Fazio, M.C. Bryan, O. Blixt, J.C. Paulson, and C.H. Wong J. Am. Chem. Soc. 124 2002 14397 14402
21. Q. Wang, R.R. Chan, R. Hilgraf, V.V. Fokin, K.B. Sharpless, and M.G. Finn J. Am. Chem. Soc. 125 2003 3192 3193
22. L.V. Lee, M.L. Mitchell, S.J. Huang, V.V. Fokin, K.B. Sharpless, and C.H. Wong J. Am. Chem. Soc. 125 2003 9588 9589
23. A.J. Link, and D.A. Tirrell J. Am. Chem. Soc. 125 2003 11164 11165
24. A.E. Speers, and B.F. Cravatt ChemBioChem 5 2004 41 47
25. C.W. Tornøe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057 3064
26. D. Michalik, J.F.G. Vliegenthart, and J.P. Kamerling J. Chem. Soc., Perkin Trans. 1 2002 1973 1981
27. Zhang, M. M. S. thesis, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, 2001.
28. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 114 2002 2596 2599
29. S. Chittaboina, F. Xie, and Q. Wang Tetrahedron Lett. 46 2005 2331 2336
30. T. Sasaki, and N. Takasuka Carbohydr. Res. 47 1976 99 104
31. G. Chihara, Y. Maeda, J. Hamura, T. Sasaki, and F. Fukuoka Nature 222 1969 687 688