Isomerization through cleavage and recombination of imidazolide linkage in the condensed tricyclic system related to hypermodified bases of phenylalanine transfer ribonucleic acids

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 10, 1999, Pages 1464-1472

  Itaya, Taisuke ^a   Kanai, Tae ^a   Ohyama, Shin Ichi ^a   Shirasaki, Yoshihisa ^a   Muramoto, Nobuhiro ^a   Ono, Yukiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Equilibrium constant; Hydrogen bonding catalysis; Imidazolide methanolysis; Linear free energy relationship; Pyrimidone fission recyclization; tRNA hypermodified base

Indexed keywords

HYDROGEN; IMIDAZOLINE; METHANOL; OXYGEN; PHENYLALANINE; RNA;

AMINO ACID TRANSPORT; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DNA CLEAVAGE; DNA RECOMBINATION; HYDROGEN BOND; ISOMERISM; STEREOCHEMISTRY;

EID: 0032753043     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.1464     Document Type: Article

References (52)

1. Staab H.A., Angew. Chem., 74, 407-423 (1962).
2. a) Itaya T., Mizutani A., Takeda M., Shioyama C., Chem. Pharm. Bull., 37, 284-291 (1989);
3. b) Itaya T., Mizutani A., Iida T., ibid., 39, 1407-1414 (1991);
4. c) References cited in ref. 2a.
5. Itaya T., Matsumoto H., Watanabe T., Harada T., Chem. Pharm. Bull., 33, 2339-2347 (1985).
6. Itaya T., Mizutani A., Watanabe N., Chem. Pharm. Bull., 37, 1221-1225 (1989).
7. Itaya T., Morisue M., Takeda M., Kumazawa Y., Chem. Pharm. Bull., 38, 2656-2661 (1990).
8. a) Ivancsics C., Zbiral E., Justus Liebigs Ann. Chem., 1975, 1934-1943;
9. b) El Khadem H. S., Kawai J., Swartz D. L., Heterocycles, 28, 239-248 (1989);
10. c) Leonard N. J., Bhat B., Wilson S. R., Cruickshank K. A., J. Am. Chem. Soc., 113, 1398-1406 (1991);
11. d) Arnold W., Büttelmann B., Heitz M.-P., Wyler R., Heterocycles, 43, 2607-2614 (1996);
12. e) See also Loakes D., Brown D. M., Salisbury S. A., Tetrahedron Lett., 39, 3865-3868 (1998) and references cited therein.
13. Treatment of piperonyl alcohol (152 mg, 1 mmol) with boiling MeOH (150 ml) for 3 h in the presence of 10% Pd-C (186 mg) did not afford the methyl ether, but produced piperonal (120 mg, 80%). Accordingly, this procedure appears to be ineffective for benzylation of alcohols.
14. a) Litchfield G. J., Shaw G., J. Chem. Soc., (B), 1971, 1474-1484;
15. b) Srivastava P. C., Mancuso R. W., Rousseau R. J., Robins R. K., J. Med. Chem., 17, 1207-1211 (1974);
16. c) Thomas H. J., Avery L. N., Brockman R. W., Montgomery J. A., ibid., 30, 431-434 (1987);
17. d) Groziak M. P., Bhat B., Leonard N. I., Proc. Natl. Acad. Sci. U.S.A., 85, 7174-7176 (1988);
18. e) Bhat B., Groziak M. P., Leonard N. J., J. Am. Chem. Soc., 112, 4891-4897 (1990);
19. f) Groziak M. P., Huan Z.-W., Ding H., Meng Z., Stevens W. C., Robinson P. D., J. Med. Chem., 40, 3336-3345 (1997).
20. Lukens L. N., Buchanan J. M., J. Biol. Chem., 234, 1799-1805 (1959).
21. Itaya T., Kanai T., Heterocycles, 46, 101-104 (1997).
22. Itaya T., Morisue M., Shimomichi M., Ozasa M., Shimizu S., Nakagawa S., J. Chem. Soc., Perkin Trans. 1, 1994, 2759-2765.
23. a) Kasai H., Goto M., Takemura S., Goto T., Matsuura S., Tetrahedron Lett., 1971, 2725-2728;
24. b) Kasai H., Goto M., Ikeda K., Zama M., Mizuno Y., Takemura S., Matsuura S., Sugimoto T., Goto T., Biochemistry, 15, 898-904 (1976).
25. EtOH nm (ε): 250 (23700), 285 (sh) (7300), 306 (10500).
26. Itaya T., Ogawa K., Tetrahedron, 38, 1767-1773 (1982).
27. Nef J. U., Justus Liebigs Ann. Chem., 335, 247-279 (1904).
28. a) Kusmierek J. T., Jensen D. E., Spengler S. J., Stolarski R., Singer B., J. Org. Chem., 52, 2374 (1987);
29. b) Khazanchi R., Yu P-L., Johnson F., ibid., 58, 2552-2556 (1993).
30. 3) δ: 3.99 (3H, s, Me), 5.71 (2H, s, CH2), 7.20 [1H, d, J=1.7 Hz, C(6)-H], 7.50 [2H, m, C(2′)-, C(6′)-H], 7.63 [1H, d, J=1.7 Hz, C(7)-H], 7.83 [1H, s, C(2)-H], 8.22 [2H, m, C(3′)-, C(5′)-H].
31. 3) δ: 4.01 (3H, s, Me), 6.04 (2H, s, CH2), 7.20 [1H, d, J=1.7 Hz, C(6)-H], 7.48-7.68 [2H, m, C(5′)-, C(6′)-H], 7.63 [1H, d, J= 1.7 Hz, C(7)-H], 7.91 [1H, s,C(2)-H], 8.13-8.23 [1H, m, C(3′)-H].
32. 30)
33. a) Charton M., J. Org. Chem., 30, 3346-3350 (1965);
34. b) Blažević N., Kajfež F., Šunjić V., J. Heterocycl. Chem., 7, 227-229 (1970);
35. c) Collis M. J., Edwards G. R., Chem. Ind. (London), 1971, 1097-1098;
36. d) Cartier O., Paubel J. P., Niviere P., C. R. Hebd. Seances Acad. Sci., Ser. C, 284, 355-357 (1977);
37. e) Tomasik P., Zalewski R., Chodzinski J., Chem. Zvesti, 33, 105-109 (1979);
38. f) Suwinski J., Salwinska E., Watras J., Widel M., Zesz. Nauk. Politech. Slask., Chem., 678, 99-105 (1981).
39. Fife T. H., Natarajan R., Werner M. H., J. Org. Chem., 52, 740-746 (1987).
40. a) Isaacs N. S., "Physical Organic Chemistry," Longman Scientific and Technical, Harlow, 1987, pp. 133-135;
41. b) Exner O., in "Advances in Linear Free Energy Relationships," ed. by Chapman N. B., Shorter J., Plenum Press, New York, 1972, pp. 1-69.
42. Smith J. H., J. Am. Chem. Soc., 98, 3598-3601 (1976).
43. Kogan R. L., Fife T. H., J. Org. Chem., 49, 5229-5232 (1984).
44. Bruice T. C., Fife T. H., J. Am. Chem. Soc., 84, 1973-1979 (1962).
45. Kupchan S. M., Eriksen S. P., Friedman M., J. Am. Chem. Soc., 88, 343-346 (1966).
46. a) Guthrie J. P., "Applications of Biochemical Systems in Organic Chemistry," Part 2, ed. by Jones J. B., Sih C. J., Perlman D., John Wiley and Sons, New York, 1976, pp. 689-691;
47. b) Activation of carbonyl groups by an intramolecular hydroxy group through hydrogen bonding has also been reported for allylation of carbonyl compounds: Yasuda M., Fujibayashi T., Baba A., J. Org. Chem., 63, 6401-6404 (1998); Ito H., Ujita Y., Tateiwa J., Sonoda M., Hosomi A., Chem. Commun., 1998, 2443-2444.
48. b) Activation of carbonyl groups by an intramolecular hydroxy group through hydrogen bonding has also been reported for allylation of carbonyl compounds: Yasuda M., Fujibayashi T., Baba A., J. Org. Chem., 63, 6401-6404 (1998); Ito H., Ujita Y., Tateiwa J., Sonoda M., Hosomi A., Chem. Commun., 1998, 2443-2444.
49. Still W. C., Kahn M., Mitra A., J. Org. Chem., 43, 2923-2925 (1978).
50. -1: 1682 (CO).
51. Assigned by comparison of the peak height of this signal with that of the other CH signal: Itaya T., Ito N., Fujii T., Chem. Pharm. Bull., 44, 594-598 (1996).
52. For example, see Bunnett J. F., "Investigation of Rates and Mechanisms of Reactions," 3rd ed., Part I, ed. by Lewis E. S., John Wiley and Sons, New York, 1974, pp. 145-153.