Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 17, 2005, Pages 5113-5144

  Morii, Yasuharu ^a   Matsuda, Hiroko ^a,b   Ohara, Keiichiro ^a   Hashimoto, Masaru ^a   Miyairi, Kazuo ^a   Okuno, Toshikatsu ^a  

^a HIROSAKI UNIVERSITY   (Japan)

^b NEW YORK UNIVERSITY   (United States)

Author keywords

selective glycosylation; selective glycosylation; 5 Thioglucopyranosyl trichloroacetimidates; endo Glycosidases

Indexed keywords

GLUCOPYRANOSIDE; MALTOSE; METHYL 4 O [4' O [4'' O (5''' THIO ALPHA DEXTRO GLUCOPYRANOSYL) 5'' THIO ALPHA DEXTRO GLUCOPYRANOSYL] 5' THIO ALPHA DEXTRO GLUCOPYRANOSYL] ALPHA DEXTRO GLUCOPYRANOSIDE; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; GLYCOSYLATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

CARBOHYDRATE SEQUENCE; GLYCOSYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; THIOGLUCOSIDES;

EID: 22844438437     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.05.028     Document Type: Article

References (38)

1. H. Driguez J. Thiem Glycoscience, Synthesis of Substrate Analogs and Mimetics 1999 Springer Berlin
2. H. Driguez J. Thiem Glycoscience, Synthesis of Oligosaccharides and Glycoconjugates 1999 Springer Berlin
3. Z.J. Witczak Curr. Med. Chem. 6 1999 165
4. U. Spohr, M. Bach, and R.G. Spiro Can. J. Chem. 71 1993 1919
5. M.K. Gurjar, R. Nagaprasad, and C.V. Ramana Tetrahedron Lett. 43 2002 7577
6. G.J. Davies, K.S. Wilson, and B. Henrissat Biochem. J. 321 1997 557
7. Y. Ding, and O. Hindsgaul Bioorg. Med. Chem. Lett. 8 1998 1215
8. M. Izumi, Y. Suhara, and Y. Ichikawa J. Org. Chem. 63 1998 4811
9. T. Shimizu, T. Nakatsu, K. Miyairi, T. Okuno, and H. Kato Biochemistry 41 2002 6651
10. U. Spohr, and M. Bach Can. J. Chem. 71 1993 1928
11. H. Matsuda, M. Hashimoto, and T. Okuno Synth. Commun. 32 2002 3347
12. H. Matsuda, J. Fujita, Y. Morii, M. Hashimoto, T. Okuno, and K. Hashimoto Tetrahedron Lett. 44 2003 4089
13. K. Ohara, H. Matsuda, M. Hashimoto, K. Miyairi, and T. Okuno Chem. Lett. 2002 626
14. H. Matsuda, K. Ohara, Y. Morii, M. Hashimoto, K. Miyairi, and T. Okuno Bioorg. Med. Chem. Lett. 13 2003 1063
15. S. Mehta, J.S. Andrews, B.D. Johnston, B. Svensson, and B.M. Pinto J. Am. Chem. Soc. 117 1995 9783
16. S. Mehta, K.L. Jordan, T. Weimar, U.C. Kreis, R.J. Batchelor, F.W.B. Einstein, and B.M. Pinto Tetrahedron: Asymmetry 5 1994 2367
17. H. Yuasa, and H. Hashimoto Rev. Heteroatom Chem. 19 1999 35
18. H. Yuasa, and H. Hashimoto Trends Glycosci. Glycobiol. 13 2001 31
19. S.H. Khan O.N. Roger Modern Methods In Carbohydrate Synthesis Vol. 1 1996 Harwood Academic Publishers GmbH Amsterdam 1
20. H. Driguez, and B. Henrissat Tetrahedron Lett. 22 1981 5061
21. Y. Oikawa, T. Yoshioka, and O. Yonemitsu Tetrahedron Lett. 23 1982 885
22. S. Hanessian Preparative Carbohydrate Chemistry 1997 Marcel Dekker New York 283
23. S. Hanessian, and J. Banoub Carbohydr. Res. 53 1977 C13
24. P.-H.A. Zollo, J.-C. Jacquinet, and P. Sinaÿ Carbohydr. Res. 122 1983 201
25. G.H. Veeneman, S.H. van Leeuwen, and J.H. van Boom Tetrahedron Lett. 31 1990 1331
26. P.J. Garegg, C. Henrichson, and T. Norberg Carbohydr. Res. 116 1983 162
27. R. Verduyn, M. Douwes, P.A.M. Klein, E.M. Mosinger, G.A. Marel, and J.H. Boom Tetrahedron 49 1993 7301
28. 3) 3.70 (1H, dd, J = 2.5, 12.9 Hz, C6HH), 3.79 (1H, br d, J = 12.9 Hz, C6HH), 4.08 (1H, m, C5H), 5.50 (1H, dd, J = 3.4, 10.3 Hz, C2H), 5.64 (1H, t, J = 10.3 Hz, C4H), 6.16 (1H, d, J = 3.4 Hz,C1H), 6.44 (1H, t, J = 10.3 Hz, C3H), 7.23-7.63 (11H, aromatic protons), 7.85-8.20 (8H, aromatic protons).
29. R. Johansson, and B. Samuelsson J. Chem. Soc. Perkin I 1984 2371
30. J. Fujita, H. Matsuda, K. Ymamoto, Y. Morii, M. Hashimoto, T. Okuno, and K. Hashimoto Tetrahedron 60 2004 6829
31. R.R. Schmidt, and K.-H. Jung Oligosaccharide Synthesis with Trichloroacetimidates 1997 Marcel Dekker New York
32. H. Yamada, and M. Nishizawa Tetrahedron Lett. 28 1987 4315
33. Spartan 04 windows Wavefunction Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612.
34. R.E. Ireland, R.C. Anderson, R. Badoud, B.J. Fitzsimmons, G.J. McGarvey, S. Thaisrivongs, and C.S. Wilcox J. Am. Chem. Soc. 105 1983 1988
35. H. Takaku, K. Kamaike, and H. Tsuchiya J. Org. Chem. 49 1984 51
36. We found that MPMBr could be stored in a freezer (-20°C) for several months without any remarkable decomposition by dissolving it in benzene (1:1 v/v).
37. S. Hanessian Preparative Carbohydrate Chemistry 1997 Marcel Dekker New York 53
38. M. Adinolfi, G. Barone, A. Iadonisi, and M. Schiattarella Tetrahedron Lett. 44 2003 3733