Convenient assembly of trimeric Le x determinants using carbosilane scaffolds by means of Huisgen cycloaddition

Tetrahedron Letters

Volumn 53, Issue 50, 2012, Pages 6793-6796

  Matsuoka, Koji ^a   Yamaguchi, Hiroki ^a   Kohzu, Tatsuya ^a   Sakamoto, Jun Ichi ^a   Koyama, Tetsuo ^a   Hatano, Ken ^a   Yamamoto, Shigeto ^b   Mori, Tsutomu ^b   Hatanaka, Kenichi ^c  

^a SAITAMA UNIVERSITY   (Japan)

^b HAYASHIBARA BIOCHEMICAL LABORATORIES INC   (Japan)

^c INSTITUTE OF INDUSTRIAL SCIENCE   (Japan)

Author keywords

Carbosilanes; Glycoclusters; Glycodendrimers; Glycosides; Huisgen cycloaddition; Lewis X

Indexed keywords

GLYCOSIDE; LECTIN; LEWIS X; SILANE DERIVATIVE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; FLUORESCENCE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE IMAGING;

EID: 84868607078     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.10.004     Document Type: Article

References (42)

1. For example, see H.C. Gooi, T. Feizi, A. Kapadia, B.B. Knowles, D. Solter, and M.J. Evans Nature (London) 292 1981 156 158
2. I. Eggens, B. Fenderson, T. Toyokuni, B. Dean, M. Stroud, and S.-I. Hakomori J. Biol. Chem. 264 1989 9476 9484
3. M.L. Phillips, E. Nudelman, F.C.A. Gaeta, M. Perez, A.K. Singhal, S.-I. Hakomori, and J.C. Paulson Science 250 1990 1130 1132
4. A. Hittelet, I. Camby, N. Nagy, H. Legendre, Y. Bronckart, C. Decaestecker, H. Kaltner, N.E. Nifant'ev, N.V. Bovin, J.-C. Pector, I. Salmon, H.-J. Gabuis, R. Kiss, and P. Yeaton Lab. Invest. 83 2003 777 787 and references cited therein
5. M.C.Z. Kasuya, L.-X. Wang, Y.C. Lee, M. Mitsuki, H. Nakajima, Y. Miura, T. Sato, K. Hatanaka, S. Yamagata, and T. Yamagata Carbohydr. Res. 329 2000 755 763
6. Y. Shimura, J. Suzuki, M.C.Z. Kasuya, K. Matsuoka, and K. Hatanaka Helv. Chim. Acta 95 2012 67 75
7. Y. Shimura, J. Suzuki, M. Muraoka, M.C.Z. Kasuya, K. Matsuoka, and K. Hatanaka Prep. Biochem. Biotechnol. 42 2012 378 392
8. +]: 711.391. Found: m/z 711.354. Spectral data of this compound are available at Supplmentary data.
9. T. Sato, M. Takashiba, R. Hayashi, X. Zhu, and T. Yamagata Carbohydr. Res. 343 2008 831 838
10. For example, see E.G. Ball, R.A. O'Neill, J.E. Schultz, J.B. Lowe, B.W. Weston, J.O. Nagy, E.G. Brown, C.J. Hobbs, and M.D. Bednarski J. Am. Chem. Soc. 114 1992 5449 5451
11. K.C. Nicolaou, N.J. Bockovich, and D.R. Carcanague J. Am. Chem. Soc. 115 1993 8843 8844
12. T. Haselhorst, T. Weimar, and T. Peters J. Am. Chem. Soc. 123 2001 10705 10714
13. Y. Nagai, N. Ito, I. Sultana, and T. Sugai Tetrahedron 64 2008 9599 9606 and references cited therein
14. For example, see P.P. Deshpande, and S.J. Danishefsky Nature (London) 387 1997 164 166
15. G. Thoma, J.T. Patton, J.L. Magnani, B. Ernst, R. Örlein, and R.O. Duthaler J. Am. Chem. Soc 121 1999 5919 5929
16. T. Buskas, Y. Li, and G.-J. Boons Chem. Eur. J. 11 2005 5457 5467
17. K. Matsuoka, T. Kohzu, T. Hakumura, T. Koyama, K. Hatano, and D. Terunuma Tetrahedron Lett. 50 2009 2593 2596
18. K. Matsuoka, R. Kaneko, T. Koyama, X.-T. Ma, Y. Esumi, T. Nakamura, K. Hatano, and D. Terunuma Bioorg. Med. Chem. Lett. 20 2010 4906 4910
19. J.-I. Sakamoto, T. Koyama, D. Miyamoto, S. Yingsakmongkon, K.I.P.J. Hidari, W. Jampangern, T. Suzuki, Y. Suzuki, Y. Esumi, T. Nakamura, K. Hatano, D. Terunuma, and K. Matsuoka Bioorg. Med. Chem. 17 2009 5451
20. H. Oka, T. Onaga, T. Koyama, C.-T. Guo, Y. Suzuki, Y. Esumi, K. Hatano, D. Terunuma, and K. Matsuoka Bioorg. Med. Chem. 17 2009 5465
21. K. Matsuoka, M. Terabatake, Y. Esumi, D. Terunuma, and H. Kuzuhara Tetrahedron Lett. 40 1999 7839 7842
22. K. Matsuoka, H. Oka, T. Koyama, Y. Esumi, and D. Terunuma Tetrahedron Lett. 42 2001 3327 3330
23. K. Matsuoka, M. Terabatake, Y. Saito, C. Hagihara, Y. Esumi, D. Terunuma, and H. Kuzuhara Bull. Chem. Soc. Jpn. 71 1998 2709 2713
24. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A. (Ed.); Wiley: New York, 1984; Vol. 1, pp 1-176.
25. P. Wu, and V.V. Fokin Aldrichimica Acta 40 2007 7 17
26. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004 2021
27. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128 1137
28. M.V. Gil, M.J. Arévalo, and Ó. López Synthesis 2007 1589 1620 and references cited therein
29. D. Terunuma, T. Kato, R. Nishio, K. Matsuoka, H. Kuzuhara, Y. Aoki, and H. Nohira Chem. Lett. 1998 59 60
30. 2).
31. K. Matsuoka, H. Yamaguchi, T. Koyama, K. Hatano, and D. Terunuma Tetrahedron Lett. 51 2010 2529 2532
32. S.-I. Nishimura, K. Matsuoka, T. Furuike, N. Nishi, S. Tokura, K. Nagami, S. Murayama, and K. Kurita Macromolecules 27 1994 157 163
33. J. Yariv, A.J. Kalb, and E. Katchalski Nature (London) 215 1967 890 891
34. I.E. Liener, N. Sharon, and I.J. Goldstein The Lectins 1986 Academic Press London and the references cited therein
35. F. Bruno, M.B. Moreno, T.M. de Oliveira, D.E. Martil, M.M. Viçoti, G.A. Bezerra, J.R.B. Abrego, B.S. Cavada, and W.F.J. de Azevedo Jr. Struct. Biol. 161 2008 133 143
36. R. Lotan, and N. Sharon Biochem. Biopys. Res. Commun. 55 1973 1340 1346
37. J.-P. Privat, F. Delmotte, G. Mialonier, P. Bouchard, and M. Monsigny Eur. J. Biochem. 47 1974 5 14
38. A.J. Kalb Biochem. Biophys. Acta 168 1968 532 536
39. Y.C. Lee Carbohydr. Res. 67 1978 509 514
40. Y.C. Lee, R.R. Townsend, M.R. Hardy, J. Lönngren, J. Arnarp, M. Haraldsson, and H. Lönn J. Biol. Chem. 258 1983 199 202
41. Y.C. Lee, and R.T. Lee Acc. Chem. Res. 28 1995 321 327
42. J.J. Lundquist, and E.J. Toone Chem. Rev. 102 2002 555 578