New nucleoside-sugar conjugates: 6-N-glycosyloxyphosphorylated adenosine derivatives as partial structures of agrocin 84

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9223-9228

  Moriguchi, Tomohisa ^a   Wada, Takeshi ^a   Sekine, Mitsuo ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE DERIVATIVE; AGROCIN 84; BACTERIOCIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0030446166     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961489a     Document Type: Article

References (45)

1. (a) Kerr, A.; Htay, H. Physiol. Plant Pathol. 1974, 4, 37.
2. (b) Murphy, P. J.; Roberts, W. P. J. Gen. Mierobiol. 1979, 114, 207.
3. (c) Holmes, B.; Roberts, W. P. J. Appl. Bacteriol. 1981, 50, 443.
4. New, P. B.; Kerr, A. J. Appl. Bacteriol. 1972, 35, 279.
5. Lopez, M. M.; Gorris, M. T.; Salcedo, C. I.; Montojo, A. M.; Miro, M. Appl. Environ. Microbiol. 1989, 55, 741.
6. McCardell, B. A.; Pootjes, C. F. Antimicrob. Agents Chemother. 1976, 10, 498.
7. Das, P. K.; Basu, M.; Chatterjee, G. C. J. Antibiot. 1978, 31, 490.
8. (a) Ryder, M. H.; Slota, J. E.; Scarim, A.; Farrand, S. K. J. Bacteriol. 1987, 169, 4184.
9. (b) Law, I. J.; Strijdom, B. W. Arch. Macrobiol. 1989, 152, 463.
10. (a) Van Zyl, F. G. H.; Strijdom, B. W.; Staphorst, J. L. Appl. Environ. Microbiol. 1986, 52, 234.
11. (b) Cooksey, D. A. Plasmid 1986, 16, 222.
12. (c) Hayman, G. T.; Farrand, S. K. J. Bacteriol. 1988, 170, 1759.
13. (d) Hayman, G. T.; Farrand, S. K. Mol. Gen. Genet. 1990, 223, 465.
14. (a) Jones, D. A.; Ryder, M. H.; Clare, B. G.; Farrand, S. K.; Kerr, A. Mol. Gen. Genet. 1988, 212, 207.
15. (b) Webster, J.; Thomson, J. Mol. Gen. Genet. 1988, 214, 142.
16. (c) Lopez, M. M.; Gorris, M. T.; Salcedo, C. I.; Montojo, A. M.; Miro, M. Appl. Environ. Microbiol. 1989, 55, 741.
17. Kerr, A.; Tate, M. E. Microbiol. Sci. 1984, 1, 1.
18. (a) Roberts, W. P.; Tate, M. E.; Kerr, A. Nature 1977, 265, 379.
19. (b) Tate, M. E.; Roberts, W. P.; Kerr, A. Nature 1979, 280, 697.
20. Caputto, R.; Leloir, L. F.; Cardini, C. E.; Paladini, A. C. J. Biol. Chem. 1950, 184, 333.
21. Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131.
22. Murphy, P. J.; Tate, M. E.; Kerr, A. Eur. J. Biochem. 1981, 115, 539.
23. Thompson, R. R.; Hamilton, R. H.; Pootjes, C. F. Antimicrob. Agents Chemother. 1979, 16, 293.
24. (a) Murray, D. H.; Prokop, J. J. Pharm. Sci. 1965, 54, 1468.
25. (b) Martinez, A. P.; Lee, W. W.; Goodman, L. J. Org. Chem. 1966, 31, 3263.
26. (c) Hansske, F.; Robins, M. J. J. Am. Chem. Soc. 1983, 105, 6736.
27. (d) Nyilas, A.; Chattopadhyaya, J. Synthesis 1986, 196.
28. (e) Kawana, M.; Kuzuhara, H. Tetrahedron Lett. 1987, 28, 4075.
29. (f) Herdewijn, P.; Balzarini, J.; Pauwels, R.; Janssen, G.; Van Aerschot, A.; De Clercq, E. Nucleosides Nucleotides 1989, 8, 1231.
30. (g) Herdewijn, P. Tetrahedron 1989, 45, 6563.
31. (a) Wright, R. S.; Khorana, H. G. J. Am. Chem. Soc. 1955, 77, 3423.
32. (b) Tener, G. M.; Wright, R. S.; Khorana, H. G. J. Am. Chem. Soc. 1956, 78, 506.
33. (c) Aspinall, G. O.; Cottrell, I. W.; Matheson, N. K. Can. J. Biochem. 1972, 50, 574.
34. Bunton, C. A.; Humeres, E. J. Org. Chem. 1969, 34, 572.
35. Vinayak, R.; Hansske, F.; Robins, M. J. J. Heterocycl. Chem. 1993, 30, 1181.
36. (a) Wada, T.; Moriguchi, T.; Sekine, M. J. Am. Chem. Soc. 1994, 116, 9901.
37. (b) Hata, T.; Yamamoto, I.; Sekine, M. Chem. Lett. 1976, 601-604.
38. Nudelman, A.; Herzig, J.; Gottlieb, H. E. Carbohydr. Res. 1987, 162, 145.
39. Caruthers, M. H. J. Am. Chem. Soc. 1986, 108, 2041.
40. Wada, T.; Sekine, M. Tetrahedron Lett. 1994, 35, 757.
41. Maryanoff, B. E.; Reitz, A. B.; Nortey, S. O. Tetrahedron 1988, 44, 3093.
42. Ferrier, R. J.; Haines, S. R. J. Chem. Soc., Perkin Trans. 1 1984, 1675.
43. Backinowsky, L. V.; Nepogod'ev, S. A.; Shashkov, A. S.; Kochetkov, N. K. Carbohydr. Res. 1985, 138, 41.
44. Ritchie, R. G. S.; Cyr, N.; Korsch, B.; Koch, H. J.; Perlin, A. S. Can. J. Chem. 1975, 53, 1424.
45. α-D-Ribofuranose 1-phosphate is hydrolyzed several hundred times faster than α-D-glucopyranose 1-phosphate under acidic conditions. See ref 17.