Synthesis of new aminoacyl-adenylate analogs having an N-acyl phosphoramidate linkage

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3725-3728

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

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE DERIVATIVE; AMINOACYL TRANSFER RNA; PHOSPHORAMIDIC ACID DERIVATIVE; TETRAZOLE DERIVATIVE;

AMINOACYLATION; ARTICLE; MOLECULAR DYNAMICS; REACTION ANALYSIS; RNA SYNTHESIS;

EID: 0032575199     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00570-X     Document Type: Article

References (27)

1. 1. (a) Hoagland, M. B. Biochim. Biophys. Acta 1955, 16, 288.
2. (b) Hoagland, M. B.; Zamecnik, P. C.; Keller, E. B. J. Biol. Chem. 1956, 218, 345.
3. 2. Friest, W. Biochemistry 1989, 28, 6787.
4. 3. Cassio, D.; Lemoine, F.; Waller, J.-P.; Sandrin, E.; Boissonnas, R. Biochemistry 1967, 6, 827.
5. 4. Dprion, C.; Chenevert, R.; Lacosta, L.; Lapointe, J.; BioMed. Chem. Lett. 1993, 3, 2699.
6. 5. Biryukov, A. I.; Ishmuratov, B. K.; Khomutov, R. M. FEBS Lett. 1978, 91, 249.
7. 6. Ueda, H.; Shoku, Y.; Hayashi, N.; Mitsunaga, J.; In, Y.; Doi, M.; Inoue, M.; Ishida, T. Biochim. Biophys. Acta 1991, 1080, 126.
8. 7. Biou, V.; Yaremchuk, A.; Tukalo, M.; Cusack, S. Science 1994, 265, 1404.
9. 8. (a) Uramoto, M.; Kim, C. J.; Shin-ya, K.; Kusakabe, H.; Isono, K. J. Antibiot. 1991, 44, 375.
10. (b) Phillips, D. R.; Uramoto, M.; Isono, K.; McCloskey, J. A. J. Org. Chem. 1993, 58, 854.
11. 9. (a) Roberts, W. P.; Tate, M. E.; Kerr, A. Nature 1977, 265, 379.
12. (b) Tate, M. E.; Murphy, P. J.; Kerr, A. Nature 1979, 280, 697.
13. 10. Challis, B. C.; Iley, J. N. J. Chem. Soc., Perkin Trans. 2 1987, 1489.
14. 11. Henddrickse, T. F.; Mizrahi, V.; Modro, T. A. Phosphorus Sulfur 1984, 20, 93.
15. 12. Mizrahi, V.; Modro, T. A. J. Org. Chem. 1982, 47, 3533.
16. 13. Chakravarty, P. K.; Greenlee, W. J.; Parsons, W. H.; Patchett, A. A.; Combs, P.; Roth, A.; Busch, R. D.; Mellin, T. N. J. Med. Chem. 1989, 32, 1886.
17. 14. Desmarchelier, J. M.; Fukuto, T. R. J. Org. Chem. 1972, 37, 4218.
18. 15. Robles, J.; Pedroso, E.; Grandas, A. J. Org. Chem. 1995, 60, 4856.
19. 16. Wada, T.; Sekine, M. Tetrahedron Lett. 1994, 35, 757.
20. 17. Gryaznov, S. M.; Letsinger, R. L. Nucleic Acid Res. 1992, 20. 1879.
21. 18. Froehler, B. C.; Matteucci, M. D. Tetrahedron Lett. 1983, 24, 3171.
22. 19. Sekine, M.; Hata, T. J. Org. Chem. 1983, 26, 3011.
23. 20. (a) Sekine, M.; Masuda, N.; Hata, T. Tetrahedron 1985, 41, 5445.
24. (b) Sekine, M.; Hata, T. Bull Chem. Soc. Jpn. 1985, 58, 336.
25. + 494.1553. Observed for m/z 494.1552.
26. + 446.1553. Observed for m/z 446.1560.
27. + 444.1397. Observed for m/z 444.1402.