Synthesis of sialyllactosamine clusters using carbosilane as core scaffolds by means of chemical and enzymatic approaches

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 16, 2010, Pages 4906-4910

  Matsuoka, Koji ^a   Kaneko, Reina ^a   Koyama, Tetsuo ^a   Ma, Xiaotao ^a   Esumi, Yasuaki ^b   Nakamura, Takemichi ^b   Hatano, Ken ^a   Terunuma, Daiyo ^a  

^a SAITAMA UNIVERSITY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Chemo enzymatic syntheses; Clusters; Glycosides; Glycosyltransferases; N Acetylglucosamine; N Acetyllactosamine; Oligosaccharides; Sialic acid; Sialyllactosamine

Indexed keywords

GALACTOSYLTRANSFERASE; GLYCOSIDE; N ACETYLGLUCOSAMINE; SIALYLLACTOSAMINE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; URIDINE DIPHOSPHATE GALACTOSE; AMINOSUGAR; CARBOSILANE; LACTOSAMINE; N ACETYLLACTOSAMINE SYNTHASE; N-ACETYLLACTOSAMINE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; ENZYME SUBSTRATE; ANIMAL; BIOSYNTHESIS; BOVINAE; CHEMISTRY; METABOLISM; RAT;

ACETYLGLUCOSAMINE; AMINO SUGARS; ANIMALS; CARBOHYDRATE SEQUENCE; CATTLE; N-ACETYLLACTOSAMINE SYNTHASE; RATS; SILANES; URIDINE DIPHOSPHATE GALACTOSE;

EID: 77955429016     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.06.066     Document Type: Article

References (32)

1. For example, M. Fukuda, and A. Kobata Glycobiology 1993 IRL Press Oxford and references cited therein
2. Y. Suzuki, T. Nakao, T. Ito, N. Watanabe, Y. Toda, X. Guiyun, T. Suzuki, T. Kobayashi, Y. Kimura, A. Yamada, K. Sugawara, H. Nishimura, F. Kitame, K. Nakamura, E. Deya, M. Kiso, and A. Hasegawa Virology 189 1992 121
3. For example, see R.G. Webster, W.J. Bean, O.T. Gorman, T.M. Chambers, and Y. Kawaoka Microbiol. Rev. 56 1992 152 and references cited therein
4. K. Ando, K. Kikugawa, and M. Beppu J. Biol. Chem. 269 1994 19394
5. H. Paulsen, and K.-M. Steiger Carbohydr. Res. 169 1987 105
6. A. Kameyama, H. Ishida, M. Kiso, and A. Hasegawa J. Carbohydr. Chem. 8 1989 799
7. A.A. Sherman, O.N. Yudina, Y.V. Mironov, E.V. Sukhova, A.S. Shashkov, V.M. Menshov, and N.E. Nifantieva Carbohydr. Res. 336 2001 13
8. K. Matsuoka, T. Onaga, T. Mori, J. Sakamoto, K. Koyama, N. Sakairi, K. Hatano, and D. Terunuma Tetrahedron Lett. 45 2004 9383
9. E.S. Simon, M.D. Bednarski, and G.M. Whitesides J. Am. Chem. Soc. 110 1988 7159
10. Y. Ichikawa, G.C. Look, and C.-H. Wong Anal. Biochem. 202 1992 215
11. M. Matsuda, and S.-I. Nishimura J. Med. Chem. 44 2001 715
12. I.M. Choudhury, N. Minoura, and H. Uzawa Carbohydr. Res. 338 2003 1265
13. K.I.P.J. Hidaril, T. Murata, K. Yoshida, Y. Takahashi, Y.-H. Minamijima, Y. Miwa, S. Adachi, M. Ogata, T. Usui, Y. Suzuki, and T. Suzuki Glycobiology 18 2008 779
14. Y.C. Lee Carbohydr. Res. 67 1978 509
15. Y.C. Lee, R.R. Townsend, M.R. Hardy, J. Lönngren, J. Arnarp, M. Haraldsson, and H. Lönn J. Biol. Chem. 258 1983 199
16. J.J. Lundquist, and E.J. Toone Chem. Rev. 102 2002 555
17. 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
18. 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
19. S. Nakabayashi, C.D. Warren, and R.W. Jeanloz Carbohydr. Res. 150 1986 C7
20. D. Terunuma, T. Kato, R. Nishio, K. Matsuoka, H. Kuzuhara, Y. Aoki, and H. Nohira Chem. Lett. 1998 59
21. D. Horton, and M.L. Wolfrom J. Org. Chem. 27 1962 1974
22. K. Matsuoka, M. Terabatake, Y. Esumi, D. Terunuma, and H. Kuzuhara Tetrahedron Lett. 40 1999 7839
23. K. Matsuoka, H. Oka, T. Koyama, Y. Esumi, and D. Terunuma Tetrahedron Lett. 42 2001 3327
24. K. Matsuoka, M. Terabatake, Y. Saito, C. Hagihara, Y. Esumi, D. Terunuma, and H. Kuzuhara Bull. Chem. Soc. Jpn. 71 1998 2709
25. K. Matsuoka, M. Terabatake, Y. Esumi, K. Hatano, D. Terunuma, and H. Kuzuhara Biomacromolecules 7 2006 2284
26. M.M. Palcic, H. Li, D. Zanini, R.S. Bhella, and R. Roy Carbohydr. Res. 305 1997 433
27. L. Reneudie, R. Daniellou, C. Augé, and C.L. Narvor Carbohydr. Res. 339 2004 693
28. J.T. Powell, and K. Brew Eur. J. Biochem. 48 1974 217
29. E.E. Boeggeman, P.V. Balaji, and P.K. Qasba Glycoconjugate J. 12 1995 865
30. K. Yamada, E. Fujita, and S.-I. Nishimura Carbohydr. Res. 305 1998 443
31. K. Brew, T.C. Vanaman, and R.L. Hill Proc. Natl. Acad. Sci. U.S.A. 59 1968 491
32. J.-I. Sakamoto, C. Takita, T. Koyama, K. Hatano, D. Terunuma, and K. Matsuoka Carbohydr. Res. 343 2008 2735