A search for pyrophosphate mimics for the development of substrates and inhibitors of glycosyltransferases

Bioorganic and Medicinal Chemistry

Volumn 5, Issue 4, 1997, Pages 661-672

  Wang, Ruo ^a   Steensma, Darryl H ^a,b   Takaoka, Yoshikazu ^a   Yun, Joanne W ^a   Kajimoto, Tetsuya ^b   Wong, Chi Huey ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GALACTOSE; GLUCOSE; GLYCOSYLTRANSFERASE; PYROPHOSPHATE; TRANSFERASE INHIBITOR;

ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SUBSTRATE;

AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTIFUNGAL; ANTIVIRAL AGENTS; BINDING SITES; DIPHOSPHATES; ENZYME INHIBITORS; FUCOSYLTRANSFERASES; MALONATES; MANGANESE; MONOSACCHARIDES; N-ACETYLLACTOSAMINE SYNTHASE; PYRIMIDINE NUCLEOSIDES; SUBSTRATE SPECIFICITY; TARTRATES; TUNICAMYCIN;

EID: 0030915738     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)00005-9     Document Type: Article

References (45)

1. Joziasse, D. H. Glycobiology 1993, 3, 97.
2. Wong, C-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 412 and 521.
3. Baguley, B. C.; Römmele, G.; Gruner, J.; Wehrli, W. Eur. J. Biochem. 1979, 97, 345.
4. (a) Endo, A.; Misato, T. Biochem. Biophys. Res. Commun. 1969, 37, 718.
5. (b) Krainer, E.; Khare, R. K.; Naider, F.; Becker, J. M. Anal. Biochem. 1987, 160, 33.
6. (c) Isono, K.; Suzuki, S. Heterocycles 1979, 13, 333.
7. (a) Tkacz, J. S.; Lampen, J. O. Biochem. Biophys. Res. Commun. 1975, 65, 248.
8. (b) Kuo, S.-C.; Lampen, J. O. Biochem. Biophys. Res. Commun. 1974, 58, 287.
9. (c) Savage, K. E.; Baur, P. S. J. Cell. Sci. 1983, 64, 295.
10. (d) Deas, J.; Erecinska, M. Brain Res. 1989, 483, 84.
11. (e) King, I. A.; Tabiowo, A. Biochem. J. 1981, 198, 331.
12. (f) Heifetz, A.; Keeman, R. W.; Elbein, A. D. Biochemistry 1979, 18, 2186.
13. Vaghefi, M. M.; Bernacki, R. J.; Dalley, N. K.; Wilson, B. E.; Robins, R. K. J. Med. Chem. 1987, 30, 1383.
14. Vaghefi, M. M.; Bernacki, R. J.; Hennen, W. J.; Robins, R. K. J. Med. Chem. 1987, 30, 1391.
15. Palcic, M. M.; Heerze, L. D.; Srivastava, O. P.; Hindsgaul, O. J. Biol. Chem. 1989, 264, 17174.
16. Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 8397.
17. Hindsgaul, O.; Kaur, K. J.; Srivastava, G.; Blaszczyk-Thurin, M.; Crawley, S. C.; Heerze, L. D.; Palcic, M. M. J. Biol. Chem. 1991, 266, 17858.
18. Qiao, L.; Murray, B. W.; Shimazaki, M.; Schultz, J.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 7653.
19. Schwarz, R. T.; Datema, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 321.
20. Palcic, M. M.; Ripka, J.; Kaur, K. J.; Shoreibah, M.; Hindsgaul, O.; Pierce, M. J. Biol. Chem. 1990, 265, 6759.
21. Camarasa. M.-J.; Fernandez-Resa. P.; Garcia-Lopez, M-T.; Heras, F. G. D. L.; Mendez-Castrillon, P. P.; Alarcon, B.; Carrasco, L. J. Med. Chem 1985, 28, 40.
22. Kijima-Suda, I.; Miyamoto, Y.; Toyoshima, S.; Itoh, M.; Osawa, T. Cancer Res. 1986, 46, 858.
23. Korytnyk, W.; Angelino, N.; Klohs, W.; Bernacki, R. Eur. J. Med. Chem. 1980, 15, 77.
24. Schmidt, R. R.; Frische, K. Bioorg. Med. Chem. Lett. 1993, 13, 1747.
25. (a) Radin, N. S.; Inokuchi, J. Biochem. Pharmacol 1988, 37, 2879. (b) Carson, K. G.; Ganem, B.; Radin, N. S.; Abe, A.; Shayman, J. A. Tetrahedron Lett. 1994, 35, 2659.
26. (a) Radin, N. S.; Inokuchi, J. Biochem. Pharmacol 1988, 37, 2879. (b) Carson, K. G.; Ganem, B.; Radin, N. S.; Abe, A.; Shayman, J. A. Tetrahedron Lett. 1994, 35, 2659.
27. Hendrickson, T. L.; Spencer, J. R.; Kato. M.; Imperiali, B. J. Am. Chem. Soc. 1996, 118, 7636.
28. Kim, S. C.; Singh, A. N.; Raushel, F. M. Arch. Biochem. Biophys. 1988, 267, 54.
29. (a) Murray, B. W.; Takayama, S.; Schultz, J.; Wong, C.-H. Biochemistry 1996, 35, 11183. (b) Murray, B. W.; Wittmann, V.; Burkart. M. D.; Hung, S.-C.; Wong, C.-H. Biochemistry, 1997, 36, 823.
30. (a) Murray, B. W.; Takayama, S.; Schultz, J.; Wong, C.-H. Biochemistry 1996, 35, 11183. (b) Murray, B. W.; Wittmann, V.; Burkart. M. D.; Hung, S.-C.; Wong, C.-H. Biochemistry, 1997, 36, 823.
31. (a) Cini, R.; Sabat, M.; Sundara Lingam, M.; Burla, M. C.; Nunzi. A.; Polidori, G.; Zanazzi, P. F. J. Biomol. Structure Dynamics 1983, 1, 633. (b) Merritt, E. A.; Sundaralingam, M. Acta Cryst. 1981, B37, 1505. Merritt, E. A.; Sundaralingam, M. Acta Cryst. 1980, B36, 2576. Shorter, A. L.; Harony, T. P.; Scalzo-Brush, T.; Knight, W. B.; Dunaway-Mariano, D.; Sundaralingam, M. Biochemistry 1987, 26, 2060. (e) Cini, R.; Burla, W. C.; Nunzi, A.; Polidori, G. P.; Zanazzi, P. F. J. Chem. Soc. Dalton Trans. 1984, 2467.
32. (a) Cini, R.; Sabat, M.; Sundara Lingam, M.; Burla, M. C.; Nunzi. A.; Polidori, G.; Zanazzi, P. F. J. Biomol. Structure Dynamics 1983, 1, 633. (b) Merritt, E. A.; Sundaralingam, M. Acta Cryst. 1981, B37, 1505. Merritt, E. A.; Sundaralingam, M. Acta Cryst. 1980, B36, 2576. Shorter, A. L.; Harony, T. P.; Scalzo-Brush, T.; Knight, W. B.; Dunaway-Mariano, D.; Sundaralingam, M. Biochemistry 1987, 26, 2060. (e) Cini, R.; Burla, W. C.; Nunzi, A.; Polidori, G. P.; Zanazzi, P. F. J. Chem. Soc. Dalton Trans. 1984, 2467.
33. (a) Cini, R.; Sabat, M.; Sundara Lingam, M.; Burla, M. C.; Nunzi. A.; Polidori, G.; Zanazzi, P. F. J. Biomol. Structure Dynamics 1983, 1, 633. (b) Merritt, E. A.; Sundaralingam, M. Acta Cryst. 1981, B37, 1505. Merritt, E. A.; Sundaralingam, M. Acta Cryst. 1980, B36, 2576. Shorter, A. L.; Harony, T. P.; Scalzo-Brush, T.; Knight, W. B.; Dunaway-Mariano, D.; Sundaralingam, M. Biochemistry 1987, 26, 2060. (e) Cini, R.; Burla, W. C.; Nunzi, A.; Polidori, G. P.; Zanazzi, P. F. J. Chem. Soc. Dalton Trans. 1984, 2467.
34. (a) Cini, R.; Sabat, M.; Sundara Lingam, M.; Burla, M. C.; Nunzi. A.; Polidori, G.; Zanazzi, P. F. J. Biomol. Structure Dynamics 1983, 1, 633. (b) Merritt, E. A.; Sundaralingam, M. Acta Cryst. 1981, B37, 1505. Merritt, E. A.; Sundaralingam, M. Acta Cryst. 1980, B36, 2576. Shorter, A. L.; Harony, T. P.; Scalzo-Brush, T.; Knight, W. B.; Dunaway-Mariano, D.; Sundaralingam, M. Biochemistry 1987, 26, 2060. (e) Cini, R.; Burla, W. C.; Nunzi, A.; Polidori, G. P.; Zanazzi, P. F. J. Chem. Soc. Dalton Trans. 1984, 2467.
35. (a) Cini, R.; Sabat, M.; Sundara Lingam, M.; Burla, M. C.; Nunzi. A.; Polidori, G.; Zanazzi, P. F. J. Biomol. Structure Dynamics 1983, 1, 633. (b) Merritt, E. A.; Sundaralingam, M. Acta Cryst. 1981, B37, 1505. Merritt, E. A.; Sundaralingam, M. Acta Cryst. 1980, B36, 2576. Shorter, A. L.; Harony, T. P.; Scalzo-Brush, T.; Knight, W. B.; Dunaway-Mariano, D.; Sundaralingam, M. Biochemistry 1987, 26, 2060. (e) Cini, R.; Burla, W. C.; Nunzi, A.; Polidori, G. P.; Zanazzi, P. F. J. Chem. Soc. Dalton Trans. 1984, 2467.
36. (a) Liu, K. K.-C.; Kajimoto, T.: Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (b) Wang, Y.-F.; Takaoka, Y.; Wong, C.-H. Angew. Chem. 1994, 106, 1343; Angew. Chem. Int. Ed. Engl. 1994, 33, 1242. (c) Wong, C.-H.; Provencher, L.; Porco, J. A. Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
37. (a) Liu, K. K.-C.; Kajimoto, T.: Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (b) Wang, Y.-F.; Takaoka, Y.; Wong, C.-H. Angew. Chem. 1994, 106, 1343; Angew. Chem. Int. Ed. Engl. 1994, 33, 1242. (c) Wong, C.-H.; Provencher, L.; Porco, J. A. Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
38. (a) Liu, K. K.-C.; Kajimoto, T.: Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (b) Wang, Y.-F.; Takaoka, Y.; Wong, C.-H. Angew. Chem. 1994, 106, 1343; Angew. Chem. Int. Ed. Engl. 1994, 33, 1242. (c) Wong, C.-H.; Provencher, L.; Porco, J. A. Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
39. (a) Liu, K. K.-C.; Kajimoto, T.: Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (b) Wang, Y.-F.; Takaoka, Y.; Wong, C.-H. Angew. Chem. 1994, 106, 1343; Angew. Chem. Int. Ed. Engl. 1994, 33, 1242. Wong, C.-H.; Provencher, L.; Porco, J. A. Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
40. Hampton, A. J. Org. Chem. 1961, 83, 3640.
41. Horwitz, J. P.; Tomson, A. J.; Urbanski, J. A.; Chua, J. J. Org. Chem. 1962, 27, 3045.
42. Ichikawa, Y.; Lin, Y.-C.; Dumas, D. P.; Shen, G.-J.; Garcia-Junceda. E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283.
43. Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777.
44. Hayakama, H.; Tanaka, H.; Maruyama, Y.; Miyasaka, T. Chem. Lett. 1985, 1401.
45. Grundler, G.; Schmidt, R. R. Carbohydrate Res. 1985, 135, 203.