Synthesis of a bisubstrate-type inhibitor of N- acetylglucosaminyltransferases

Angewandte Chemie - International Edition

Volumn 43, Issue 42, 2004, Pages 5674-5677

  Hanashima, Shinya ^a   Manabe, Shino ^b   Inamori, Kei Ichiro ^c   Taniguchi, Naoyuki ^c   Ito, Yukishige ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b RIKEN   (Japan)

^c OSAKA UNIVERSITY MEDICAL SCHOOL   (Japan)

Author keywords

Bisubstrates; Glycoproteins; Inhibitors; Solid phase synthesis; Transferases

Indexed keywords

ENZYMES; POLYMERS; RESINS; SYNTHESIS (CHEMICAL);

ONE-POT LIGATION; TRANSFER INTERFERENCE;

ORGANIC COMPOUNDS;

ENZYME INHIBITOR; N ACETYLGLUCOSAMINYLTRANSFERASE; POLYMER; PYROPHOSPHATE; RESIN;

AQUEOUS SOLUTION; ARTICLE; ENZYME INHIBITION; ENZYME SUBSTRATE; EVALUATION; HYBRID; REACTION ANALYSIS; SYNTHESIS;

ARYLAMINE N-ACETYLTRANSFERASE; BINDING SITES; ENZYME INHIBITORS; KINETICS; MODELS, CHEMICAL; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; TRISACCHARIDES; URIDINE DIPHOSPHATE N-ACETYLGLUCOSAMINE; URIDINE MONOPHOSPHATE;

EID: 8444232865     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460388     Document Type: Article

References (41)

1. Handbook of Glycosyltransferases and Related Genes (Eds.: N. Taniguchi, K. Honke, M. Fukuda), Springer, Tokyo, 2002.
2. a) I. Brockhausen, J. P. Carver, H. Schachter, Biochem. Cell Biol. 1988, 66. 1134-1151;
3. b) R. D. Cummings, I. S. Trowbridge, S. Kornfeld, J. Biol. Chem. 1982, 257, 13421-13427.
4. K. Inamori, T. Endo, Y. Ide, S. Fujii, J. Gu, K. Honke, N. Taniguchi, J. Biol. Chem. 2003. 278, 43102-43109.
5. K. Inamori, T. Endo, J. Gu, I. Matsuo, Y. Ito, S. Fujii, H. Iwasaki, H. Narimatsu, E. Miyoshi, K. Honke, N. Taniguchi, J. Biol. Chem. 2004, 279. 2337-2340.
6. J. W. Dennis, M. Granovsky, C. E. Warren, Biochim. Biophys. Acta 1999, 1473, 21-34.
7. a) J. W. Dennis, S. Laferte, C. Waghorne, M. L. Breitman, R. S. Kerbel, Science 1987, 236, 582-585;
8. b) S. Ihara, E. Miyoshi, J. Ko, K. Murata, S. Nakahara, K. Honke, R. B. Dickson, C.-Y. Lin, N. Taniguchi, J. Biol. Chem. 2002, 277, 16960-16967;
9. c) M. Demetriou, I. R. Nabi, M. Coppolino, S. Dedhar, J. W. Dennis, J. Cell Biol. 1995, 130, 383-392;
10. d) H.-B. Guo, I. Lee, M. Kamar, S. K. Akiyama, M. Pierce, Cancer Res. 2002, 62, 6837-6845;
11. e) H.-B. Guo, I. Lee, M. Kamar, M. Pierce, J. Biol. Chem. 2003, 278, 52 412-52 424;
12. f) M. Demetriou, M. Granovsky, S. Quaggin, J. W. Dennis, Nature 2001, 409, 733-739;
13. g) T. Saito, E. Miyoshi, K. Sasai, N. Nakano, H. Eguchi, K. Honke, N. Taniguchi, J. Biol. Chem. 2002, 277, 17002-17008.
14. M. Granovsky, J. Fata, J. Pawling, W. J. Muller, R. Khokha, J. W. Dennis, Nat. Med. 2000, 6, 306-312.
15. J. W. Dennis, J. Pawling, P. Cheung, E. Partridge, M. Demetriou, Biochim. Biophys. Acta 2002, 1573, 414-422.
16. a) P.-P. Lu, O. Hindsgaul, H. Li, M. M. Palcic, Carbohydr. Res. 1997, 303, 283-291;
17. b) I. Brockhausen, F. Reck, W. Kuhns, S. Khan, K. L. Matta, E. Meinjohanns, H. Paulsen, R. N. Shah, M. A. Baker, H. Schachter, Glycoconjugate J. 1995, 12, 371-379.
18. Previous reports on bisubstrate-type glycosyltransferase inhibitors: a) H. Hashimoto, T. Endo, Y. Kajihara, J. Org. Chem. 1997, 62, 1914-1915;
19. b) B. Waldscheck, M. Streiff, W. Notz, W. Kinzy, R. R. Schmidt, Angew. Chem. 2001, 113, 4120-4124; Angew. Chem. Int. Ed. 2001, 40, 4007-4011;
20. b) B. Waldscheck, M. Streiff, W. Notz, W. Kinzy, R. R. Schmidt, Angew. Chem. 2001, 113, 4120-4124; Angew. Chem. Int. Ed. 2001, 40, 4007-4011;
21. c) H. Hinou, X.-L. Sun, Y. Ito, J. Org. Chem. 2003, 68, 5602-5613.
22. I. Tvaroska, I. Andre, J. P. Carver, J. Am. Chem. Soc. 2000, 122, 8762-8776.
23. S. H. Tahir, O. Hindsgaul, Can. J. Chem. 1986, 64, 1771-1780.
24. a) H. Ando, S. Manabe, Y. Nakahara, Y. Ito, J. Am. Chem. Soc. 2001, 123, 3848-3849;
25. b) H. Ando, S. Manabe, Y. Nakahara, Y. Ito, Angew. Chem. 2001, 113, 4861-4864; Angew. Chem. Int. Ed. 2001, 40, 4725-4728;
26. b) H. Ando, S. Manabe, Y. Nakahara, Y. Ito, Angew. Chem. 2001, 113, 4861-4864; Angew. Chem. Int. Ed. 2001, 40, 4725-4728;
27. c) Y. Ito, S. Manabe, Chem. Eur. J. 2002, 8, 3076-3084;
28. d) S. Hanashima, S. Manabe, Y. Ito, Synlett 2003, 979-982.
29. L. Jian, C. Hartley, T.-H. Chan, Chem. Commun. 1996, 2193-2194.
30. G. Hodosi, P. Kovác, Carbohydr. Res. 1998, 308, 63-75.
31. a) P. Konradsson, D. R. Mootoo, R. E. McDevitt, B. Fraser-Reid, J. Chem. Soc. Chem. Commun. 1990, 270-272;
32. b) G. H. Veeneman, S. H. van Leeuwen, J. H. van Boom, Tetrahedron Lett. 1990, 37, 1331-1334.
33. In this particular case, use of a catalytic amount of TfOH afforded the corresponding orthoester exclusively.
34. C. A. A. van Boeckel, T. Beetz, Tetrahedron Lett. 1983, 24, 3775-3778.
35. Hydrogenolysis in EtOH caused 3-0-deacetylation as a side reaction.
36. Preparation of bis(allyloxy)diisopropylaminophosphine 19: W. Bannwarth, E. Kung, Tetrahedron Lett. 1989, 30, 4219-4222.
37. M. M. Sim, H. Kondo, C.-H. Wong, J. Am. Chem. Soc. 1993, 115, 2260-2267.
38. V. Wittmann, C.-H. Wong, J. Org. Chem. 1997, 62, 2144-2147.
39. -: 1335.36; found: 1335.32.
40. K. Sasai, Y. Ikeda, T. Fujii, T. Tsuda, N. Taniguchi, Glycobiology 2002, 12, 119-127.
41. N. Taniguchi, A. Nishikawa, S. Fujii, J. G. Gu, Methods Enzymol. 1989, 119, 397-408.