An efficient synthesis of cyclic IDP- and cyclic 8-bromo-IDP-carbocyclic-riboses using a modified hata condensation method to form an intramolecular pyrophosphate linkage as a key step. An entry to a general method for the chemical synthesis of cyclic ADP-ribose analogues

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5238-5248

  Fukuoka, Masayoshi ^a   Shuto, Satoshi ^a   Minakawa, Noriaki ^a   Ueno, Yoshihito ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE DIPHOSPHATE; ADENOSINE DIPHOSPHATE RIBOSE; AMINE; BROMINE DERIVATIVE; CYCLIC NUCLEOTIDE; HYPOXANTHINE DERIVATIVE; INOSINE DERIVATIVE; IODINE; PHOSPHOROTHIOIC ACID DERIVATIVE; PYROPHOSPHATE; RIBOSE; SILVER NITRATE;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034714481     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0000877     Document Type: Article

References (46)

1. This paper constitutes part 195 of Nucleosides and Nucleotides. Part 194: Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394.
2. Clapper, D. L.; Walseth, T. F.; Dargie, P. J.; Lee, H. C. J. Biol. Chem. 1987, 262, 9561-9568.
3. (a) Galione, A. Science 1993, 259, 325-326.
4. (b) Lee, H. C.; Galione A.; Walseth, T. F. Vitam. Horm. (San Diego) 1994, 48, 199-257.
5. (c) Dousa, T. P.; Chini, E. N.; Beers, K. W. Am. J. Physiol. 1996, 277, C1007-C1024.
6. (d) Lee H. C. Physiol. Rev. 1997, 77, 1133-1164.
7. (e) Lee, H. C. Cell Biochem. Biophys. 1998, 28, 1-17.
8. (f) Galione, A.; Cui, Y.; Empson, R; Iino, S.; Wilson, H.; Terrar, D. Cell Biochem. Biophys. 1998, 28, 19-30.
9. (g) Guse, A. H. Cell Signalling 1999, 11, 309-316.
10. (a) Walseth, T. F.; Lee, H. C. Biochim. Biophys. Acta 1993, 1178, 235-242.
11. (b) Lee, H. C.; Aarhus, R.; Walseth, T. P. Science 1993, 261, 352-355.
12. (c) Graeff, R. M.; Walseth, T. J.; Fryxell, K.; Branton, W. D.; Lee, H. C. J. Biol. Chem. 1994, 269, 30260-30267.
13. (d) Zhang, F.-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 1701-1706.
14. (e) Zhang, F.-J.; Gu, Q.-M.; Jing, P. C.; Sih, C. J. Bioorg. Med. Chem. Lett. 1995, 5, 2267-2272.
15. (f) Zhang, F.-J.; Yamada, S.; Gu, Q.-M.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 1203-1208.
16. (g) Zhang, F.-J.; Sih, C. J. Tetrahedron Lett. 1995, 63, 9289-9292.
17. (h) Zhang, F.-J.; Sih, C. J. Bioorg. Med. Chem. Lett. 1996, 6, 2311-2316.
18. (i) Ashamu, G. A.; Galione, A.; Potter, B. V. L. J. Chem. Soc., Chem. Commun. 1995, 1359-1356.
19. (j) Bailey, B. C.; Fortt, S. M.; Summerhill, R. J.; Galione, A.; Potter, B. V. L. FEBS Lett. 1996, 379, 227-230.
20. (k) Bailey, V. C.; Sethi, J. K.; Fortt, S. M.; Galione, A.; Potter, B. V. L. Chem. Biol. 1997, 4, 51-60.
21. (l) Bailey, V. C.; Sethi, J. K.; Galione, A.; Potter, B. V. L. J. Chem. Soc., Chem. Commun. 1997, 695-696.
22. (m) Sethi, J. K.; Empson, R. M.; Bailey, V. C.; Potter, B. V. L. Galione, A J. Biol. Chem. 1997, 272, 16358-16363.
23. (n) Ashamu, G. A.; Sethi, J. K; Galione, A.; Potter, B. V. L. Biochemistry 1997, 36, 9509-9517.
24. (o) Zhang, F.-J.; Gu, Q.-M.; Sih, C. J. Bioorg. Med. Chem. 1999, 7, 653-664.
25. (p) Wong, L.; Aarhus, R.; Lee, H. C.; Walseth, T. F. Biochim. Biophys. Acta 1999, 1472, 555-564.
26. Lee, H. C.; Aarhus, R. Biochim. Biophys. Acta 1993, 1164, 68-74.
27. Shuto, S.; Shirato, M.; Sumita, Y.; Ueno, Y.; Matsuda, A. J. Org. Chem. 1998, 52, 1986-1994.
28. Synthetic approaches to carbocyclic analogues of cADP-ribose have been published by other groups. Although the N-1-carbocyclic inosine and adenosine structures have been constructed, formation of the intramolecular pyrophosphate linkage has not been achieved. (a) Fortt, S.; Potter, B. V. L. Tetrahedron Lett. 1997, 38, 5371-5374.
29. (b) Hutchinson, E. J.; Taylor, B. F.; Blackburn, G. M. J. Chem. Soc., Chem. Commun. 1997, 1859-1860.
30. Gu, Q.-M.; Sih, C. J. J. Am. Chem. Soc. 1994, 116, 7481-7486.
31. (a) Nakagawa, I.; Kony, S.; Ohtani, S.; Hata, T. Synthesis 1980, 556-557.
32. (b) Sekine, M.; Kamimura, T.; Hata, T. J. Chem. Soc., Perkin Trans. 1 1985, 997-1000.
33. (c) Sekine, M.; Nishiyama, S.; Kamimura, T.; Osaki, Y.; Hata, T. Bull. Chem. Soc. Jpn. 1985, 58, 850-860.
34. (d) Fukuoka, K.; Suda, F.; Suzuki, R.; Ishikawa, M.; Takaku, H.; Hata, T. Nucleosides Nucleotides 1994, 13, 1557-1567.
35. A preliminary account of this study has been published previously: Fukuoka, M.; Shuto, S.; Minakawa, N.; Ueno, Y.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5361-5364.
36. Although a predominance of anti-over syn-conformers is well-known for natural nucleosides and their analogues, introducing a bulky substituent, such as a bromo group, into the 8-position of purine nucleosides restricts the conformation in a syn-form, through steric repulsion for the ribose moiety: Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1983.
37. Shuto, S.; Shirato, M.; Sumita, Y.; Ueno, Y.; Matsuda, A. Tetrahedron Lett. 1998, 39, 7341-7344.
38. +: see ref 9c.
39. De Napoli, L.; Messere, A.; Montesrchio, D.; Piccialli, G.; Varra, M. J. Chem. Soc., Perkin Trans. 1 1997, 2079-2082: N-1-dinitrophenylinosine derivatives were obtained as a mixture of two rotamers at the N-1-position.
40. The carbocyclic amine 18 was recovered in 87% yield after the reaction and was used repeatedly.
41. Ivanovics, G. A.; Rousseau, R. J.; Kawana, M.; Srivastava, P. C.; Robins, R. K. J. Org. Chem. 1974, 39, 3651-3654.
42. Sasse, K. Methoden der Organiches Chemie; 1971; Vol. 12, No. 2, pp 444-450.
43. Smrt, J. Tetrahedron Lett. 1973, 47, 4727-4728.
44. Sekine, M.; Hamaoki, K.; Hata, T. Bull. Chem. Soc. Jpn. 1981, 54, 3815-3827.
45. Hata, T.; Kamimura, T.; Urakami, K.; Kohno, K.; Sekine, M.; Kumagai, I.; Shinozaki, K.; Miura, K. Chem. Lett. 1987, 117-120.
46. 3 gave the desired 5′-phosphate 13 as a sole product.