Toward partial fucosyl transferase transition state analogues: Methylene sulfono sulfonamide as surrogate of pyrophosphate

Tetrahedron Letters

Volumn 44, Issue 30, 2003, Pages 5715-5718

  Carchon, Gérald ^a   Chrétien, Françoise ^a   Chapleur, Yves ^a  

^a NANCY UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

FUCOSYLTRANSFERASE; PYROPHOSPHORIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COVALENT BOND; SAPONIFICATION; SYNTHESIS;

EID: 0037828866     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01305-4     Document Type: Article

References (40)

1. Kannagi R. Glycoconj. J. 14:1997;577-584.
2. Lasky L.A. Science. 258:1992;964-969.
3. Albelda S.M., Smith C.W., Ward P.A. FASEB J. 8:1994;504-512.
4. Giannis A. Angew. Chem., Int. Ed. Engl. 33:1994;178-180.
5. Macher B.A., Holmes E.H., Swiedler S.J., Stults C.L., Srnka C.A. Glycobiology. 1:1991;577-584.
6. Oriol R., Mollicone R., Cailleau A., Balanzino L., Breton C. Glycobiology. 9:1999;323-334.
7. Palcic M.M., Heerze L.D., Srivastava O.P., Hindsgaul O.J. Biol. Chem. 264:1989;17174-17181.
8. Carbohydrate Mimics; Chapleur Y., Ed.; Weinheim: Wiley-VCH, 1998; pp. 143-155.
9. Compain P., Martin O.R. Bioorg. Med. Chem. 9:2001;3077-3092.
10. Qiao L., Murray B.W., Shimazaki M., Schultz J., Wong C.H. J. Am. Chem. Soc. 118:1996;7653-7662.
11. van der Marel G.A., Heskamp B.M., Veeneman G.H., van Boeckel C.A.A., van Boom J.H. Design and synthesis of potential fucosyl transferase inhibitors. Chapleur Y. Carbohydrate Mimics. 1998;491-510 Weinheim, Wiley-VCH.
12. Muller B., Schaub C., Schmidt R.R. Angew. Chem., Int. Ed. Engl. 37:1998;2893-2897.
13. Amann F., Schaub C., Muller B., Schmidt R.R. Chem. Eur. J. 4:1998;1106-1115.
14. Wischnat R., Martin R., Wong C.H. J. Org. Chem. 63:1998;8361-8365.
15. Schroder P.N., Giannis A. Angew. Chem., Int. Ed. Engl. 38:1999;1379-1380.
16. Schaub C., Muller B., Schmidt R.R. Eur. J. Org. Chem. 2000;1745-1758.
17. Mitchell M.L., Lee L.V., Wong C.H. Tetrahedron Lett. 43:2002;5691-5693.
18. Bhattacharya A.K., Stolz F., Kurzeck J., Ruger W., Schmidt R.R. Bioorg. Med. Chem. 10:2002;1129-1136.
19. Tanaka T., Ozawa M., Miura T., Inazu T., Tsuji S., Kajimoto T. Synlett. 2002;1487-1490.
20. For a survey of different pyrophosphate mimics, see: Wang R., Steensma D.H., Takaoka Y., Yun J.W., Kajimoto T., Wong C.-H. Bioorg. Med. Chem. 5:1997;661-672.
21. Heskamp B.M., van der Marel G.A., van Boom J.H. J. Carbohydr. Chem. 14:1995;1265-1277.
22. Heskamp B.M., Veeneman G.H., van der Marel G.A., van Boeckel C.A.A., van Boom J.H. Tetrahedron. 51:1995;8397-8406 see also Ref. 7 and references cited therein.
23. (c) see also Ref. 7 and references cited therein.
24. Carchon G., Chrétien F., Delannoy P., Verbert A., Chapleur Y. Tetrahedron Lett. 42:2001;8821-8824.
25. For the use of sulfone as phosphate surrogate, see: (a) Schneider, K. C.; Benner, S. A. Tetrahedron Lett. 1990, 31, 335-338; (b) Huang, Z.; Schneider, K. C.; Benner, S. A. Methods. Mol. Biol. 1993, 20, 315-353; (c) Reynolds, R. C.; Crooks, P. A.; Maddry, J. A.; Akthar, M. S.; Montgomery, J. A.; Secrist, J. A., III J. Org. Chem. 1992, 57, 2983-2985; (d) Richert, C.; Roughton, A. L.; Benner, S. A. J. Am. Chem. Soc. 1996, 118, 4518-4531.
26. For the use of sulfone as phosphate surrogate, see: (a) Schneider, K. C.; Benner, S. A. Tetrahedron Lett. 1990, 31, 335-338; (b) Huang, Z.; Schneider, K. C.; Benner, S. A. Methods. Mol. Biol. 1993, 20, 315-353; (c) Reynolds, R. C.; Crooks, P. A.; Maddry, J. A.; Akthar, M. S.; Montgomery, J. A.; Secrist, J. A., III J. Org. Chem. 1992, 57, 2983-2985; (d) Richert, C.; Roughton, A. L.; Benner, S. A. J. Am. Chem. Soc. 1996, 118, 4518-4531.
27. For the use of sulfone as phosphate surrogate, see: (a) Schneider, K. C.; Benner, S. A. Tetrahedron Lett. 1990, 31, 335-338; (b) Huang, Z.; Schneider, K. C.; Benner, S. A. Methods. Mol. Biol. 1993, 20, 315-353; (c) Reynolds, R. C.; Crooks, P. A.; Maddry, J. A.; Akthar, M. S.; Montgomery, J. A.; Secrist, J. A., III J. Org. Chem. 1992, 57, 2983-2985; (d) Richert, C.; Roughton, A. L.; Benner, S. A. J. Am. Chem. Soc. 1996, 118, 4518-4531.
28. For the use of sulfone as phosphate surrogate, see: (a) Schneider, K. C.; Benner, S. A. Tetrahedron Lett. 1990, 31, 335-338; (b) Huang, Z.; Schneider, K. C.; Benner, S. A. Methods. Mol. Biol. 1993, 20, 315-353; (c) Reynolds, R. C.; Crooks, P. A.; Maddry, J. A.; Akthar, M. S.; Montgomery, J. A.; Secrist, J. A., III J. Org. Chem. 1992, 57, 2983-2985; (d) Richert, C.; Roughton, A. L.; Benner, S. A. J. Am. Chem. Soc. 1996, 118, 4518-4531.
29. For the synthesis of sugar sulfonates, see: (a) Musicki, B.; Widlanski, T. S. J. Org. Chem. 1990, 55, 4231-4233; (b) Gervay, J.; Flaherty, T. M.; Holmes, D. Tetrahedron 1997, 53, 16355-16364.
30. For the synthesis of sugar sulfonates, see: (a) Musicki, B.; Widlanski, T. S. J. Org. Chem. 1990, 55, 4231-4233; (b) Gervay, J.; Flaherty, T. M.; Holmes, D. Tetrahedron 1997, 53, 16355-16364.
31. For new reagents for methylene disulfone synthesis see: (a) Hadd, M. J.; Smith, M. A.; Gervay-Hague, J. Tetrahedron Lett. 2001, 42, 5137-5140; (b) Zhu, Y. M.; Drueckhammer, D. G. Tetrahedron Lett. 2002, 43, 1377-1379.
32. For new reagents for methylene disulfone synthesis see: (a) Hadd, M. J.; Smith, M. A.; Gervay-Hague, J. Tetrahedron Lett. 2001, 42, 5137-5140; (b) Zhu, Y. M.; Drueckhammer, D. G. Tetrahedron Lett. 2002, 43, 1377-1379.
33. Wong C.H., Moris-Vara F., Hung S.C., Marron T.G., Lin C.C., Gong K.W., Weitz-Schmidt G. J. Am. Chem. Soc. 119:1997;8152-8158.
34. 2), 119.5 (C-5), 137.3 (C-8), 148.0 (C-4), 157.4 (C-2), 157.8 (-N=CH-), 158.3 (C-6), 162.6 (C-1‴).
35. Vincent S., Mioskowski C., Lebeau L. J. Org. Chem. 64:1999;991-997.
36. +.
37. Elliott R.D., Brockman R.W., Montgomery J.A. J. Med. Chem. 29:1986;1052-1056.
38. 2), 120.3 (C-5), 137.4 (C-8), 147.7 (C-4), 157.9 (-N=CH-), 158.1 (C-6).
39. +.
40. Sasaki T., Minamoto K., Itoh H. Tetrahedron. 36:1980;3509-3515.