Synthesis of 2-C-branched derivatives of d-mannose: 2-C-aminomethyl-d-mannose binds to the human C-type lectin DC-SIGN with affinity greater than an order of magnitude compared to that of d-mannose

Tetrahedron Asymmetry

Volumn 18, Issue 12, 2007, Pages 1502-1510

  Mitchell, Daniel A ^c   Jones, Nigel A ^a   Hunter, Stuart J ^a   Cook, Joseph M D ^a   Jenkinson, Sarah F ^a   Wormald, Mark R ^b   Dwek, Raymond A ^b   Fleet, George W J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 C AMINOMETHYL DEXTRO MANNOSE; 2 C AZIDOMETHYL DEXTRO MANNOSE; C TYPE LECTIN; CD209 ANTIGEN; FRUCTOSE; INTERCELLULAR ADHESION MOLECULE 3; LECTIN; MANNOSE; MEMBRANE PROTEIN; MONOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; KILIANI ACETONATION; PRIORITY JOURNAL; PROTEIN BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SURFACE PLASMON RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 34447500380     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.06.003     Document Type: Article

References (40)

1. Sun Y.X., Hayakawa S., Ogawa M., and Izumori K. Food Control 18 (2007) 220-227
2. Levin G.V. J. Med. Food 5 (2002) 23-36
3. Howling, D.; Callagan, J. L. PCT Int. App. WO 2000042865, 2000.
4. Bertelsen H., Jensen B.B., and Buemann B. World Rev. Nutr. Diet. 85 (1999) 98-109
5. Skytte U.P. Cereal Foods World 47 (2002) 224
6. Izumori K. J. Biotechol. 124 (2006) 717-722
7. Granstrom T.B., Takata G., Tokuda M., and Izumori K. J. Biosci. Bioeng. 97 (2004) 89-94
8. Izumori K. Naturwissenschaften 89 (2002) 120-124
9. Morimoto K., Park C.S., Ozaki M., Takeshita K., Shimonishi T., Granstrom T.B., Takata G., Tokuda M., and Izumori K. Enzyme Microb. Technol. 38 (2006) 855-859
10. Yoshihara K., Shinohara Y., Hirotsu T., and Izumori K. J. Biosci. Bioeng. 101 (2006) 219-222
11. Matsuo T., Baba Y., Hashiguchi M., Takeshita K., Izumori K., and Suzuki H. J. Clin. Biochem. Nutr. 30 (2001) 55-65
12. Matsuo T., and Izumori K. Biosci. Biotechnol. Biochem. 70 (2006) 2081-2085
13. Matsuo T., Shirai Y., and Izumori K. FASEB J. 20 (2006) A594
14. Matsuo T., Tanaka T., Hashiguchi M., Izumori K., and Suzuki H. Asia Pac. J. Clin. Nutr. 12 (2003) 225-231
15. Matsuo T., Tanaka T., Hashiguchi M., Izumori K., and Suzuki H. J. Nutr. Sci. Vitaminology 48 (2002) 512-516
16. Nakajima Y., Gotanda T., Uchimiya H., Furukawa T., Haraguchi M., Ikeda R., Sumizawa T., Yoshida H., and Akiyama S. Cancer Res. 64 (2004) 1794-1801
17. Simonsson E., Karlsson S., and Ahren B. Diabetes 47 (1998) 1436-1443
18. Feng L., Senchenkova S.N., Yang J.H., Shashkov A.S., Tao J., Guo H.J., Zhao G., Knirel Y.A., Reeves P., and Wang L. J. Bacteriol. 186 (2004) 383-392
19. Hajko J., Liptak A., and Pozsgay V. Carbohydr. Res. 321 (1999) 116-120
20. Kimura S., Zhang G.X., Nishiyama A., Nagai Y., Nakagawa T., Miyanaka H., Fujisawa Y., Miyatake A., Nagai T., Tokuda M., and Abe Y. J. Hypertens. 23 (2005) 1887-1894
21. Sui L., Dong Y.Y., Watanabe Y., Yamaguchi F., Hatano N., Izumori K., and Tokuda M. Anticancer Res. 25 (2005) 2639-2644
22. Hossain M.A., Izuishi K., Tokuda M., Izumori K., and Maeta H. J. Hepatobil. Pancreatic. Surg. 11 (2004) 181-189
23. Hossain M.A., Wakabayashi H., Izuishi K., Okano K., Yachida S., Tokuda M., Izumori K., and Maeta H. J. Biosci. Bioeng. 101 (2006) 369-371
24. Sui L., Dong Y.Y., Watanabe Y., Yamaguchi F., Hatano N., Tsukamoto I., Izumori K., and Tokuda M. Int. J. Oncol. 27 (2005) 907-912
25. Zehner, L.; Levin, G. V.; Saunders, J. P.; Beadle, J. R. US Patent 5356879, 1994.
26. Donner T.W., Wilber J.F., and Ostrowski D. Diabetes, Obesity Metabolism 1 (1999) 285-291
27. Menavuvu B.T., Poonperm W., Leang K., Noguchi N., Okada H., Morimoto K., Granstrom T.B., Takada G., and Izumori K. J. Biosci. Bioeng. 101 (2006) 340-345
28. Takata M.K., Yamaguchi F., Nakanose Y., Watanabe Y., Hatano N., Tsukamoto I., Nagata M., Izumori K., and Tokuda M. J. Biosci. Bioeng. 100 (2005) 511-516
29. Hotchkiss D.J., Soengas R., Booth K.V., Weymouth-Wilson A.C., Eastwick-Field V., and Fleet G.W.J. Tetrahedron Lett. 48 (2007) 517-520
30. Hotchkiss D.J., Jenkinson S.F., Storer R., Heinz T., and Fleet G.W.J. Tetrahedron Lett. 47 (2006) 315-318
31. Soengas R., Izumori K., Simone M.I., Watkin D.J., Skytte U.P., Soetart W., and Fleet G.W.J. Tetrahedron Lett. 46 (2005) 5755-5759
32. Hotchkiss D.J., Soengas R., Simone M.I., van Ameijde J., Hunter S., Cowley A.R., and Fleet G.W.J. Tetrahedron Lett. 45 (2004) 9461-9464
33. Feinberg H., Mitchell D.A., Drickamer K., and Weis W.I. Science 294 (2001) 2163-2166
34. Koppel E.A., van Gisbergen K.P., Geijtenbeek T.B., and van Kooyk Y. Cell Microbiol. 7 (2005) 157-165
35. Geijtenbeek T.B., Torensma R., van Vliet S.J., van Duijnhoven G.C., Adema G.J., van Kooyk Y., and Figdor C.G. Cell 100 (2000) 575-585
36. Guo Y., Feinberg H., Conroy E., Mitchell D.A., Alvarez R., Blixt O., Taylor M.E., Weis W.I., and Drickamer K. Nat. Struct. Mol. Biol. 11 (2004) 591-598
37. Mitchell D.A., Fadden A.J., and Drickamer K. J. Biol. Chem. 276 (2001) 28939-28945
38. Weis W.I., Drickamer K., and Hendrickson W.A. Nature 360 (1992) 127-134
39. Jones N.A., Jenkinson S.F., Soengas R., Fanefjord M., Wormald M.R., Dwek R.A., Kiran G.P., Devendar R., Takata G., Morimoto K., Izumori K., and Fleet G.W.J. Tetrahedron: Asymmetry 18 (2007) 774-786
40. Witczak Z.J., and Whistler R.L. Carbohydr. Res. 133 (1984) 235-245