Rapid synthetic route toward structurally modified derivatives of cyclic adenosine 5′-diphosphate ribose

Journal of Organic Chemistry

Volumn 70, Issue 12, 2005, Pages 4810-4819

  Wagner, Gerd K ^a,c   Guse, Andreas H ^b   Potter, Barry V L ^a  

^a University of Bath   (United Kingdom)

^b UNIVERSITY MEDICAL CENTER HAMBURG EPPENDORF   (Germany)

^c UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM; ENZYMES; PHOSPHATES; POSITIVE IONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CADPR; CYCLIC ADENOSINE 5′-DIPHOSPHATE RIBOSE; CYCLIC DINULEOTIDES; T-LYMPHOCYTES;

DERIVATIVES;

CYCLIC 8 AMINOINOSINE 5' DIPHOSPHATE RIBOSE; CYCLIC 8 AZIDOINOSINE 5' DIPHOSPHATE RIBOSE; CYCLIC 8 BROMOINOSINE 5' DIPHOSPHATE RIBOSE; CYCLIC 8 PHENYLINOSINE 5' DIPHOSPHATE RIBOSE; CYCLIC ADENOSINE DIPHOSPHATE RIBOSE; CYCLIC INOSINE 5' DIPHOSPHATE RIBOSE; DINUCLEOTIDE; INOSINE PHOSPHATE; UNCLASSIFIED DRUG;

AGONIST; ARTICLE; BIOSYNTHESIS; CALCIUM TRANSPORT; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLIZATION; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; REACTION ANALYSIS; SECOND MESSENGER; STRUCTURE ANALYSIS;

ANIMALS; APLYSIA; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIC ADP-RIBOSE; MOLECULAR STRUCTURE;

EID: 20344397685     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050085s     Document Type: Article

References (50)

1. 2+ signalling have recently appeared in Focus on Calcium. Nature Rev. Mol. Cell Biol. 2003, Vol. 4, No. 7
2. and Regulators of Calcium Signalling and Cellular Function. Curr. Mol. Med. 2004, Vol. 4, No. 4.
3. Lee, H. C. Curr. Mol. Med. 2004, 4, 227-237.
4. Potter, B. V. L.; Walseth, T. F. Curr. Mol. Med. 2004, 4, 303-311.
5. Shuto, S.; Matsuda, A. Curr. Med. Chem. 2004, 11, 827-845.
6. Shuto, S.; Shirato, M.; Sumita, Y.; Ueno, Y.; Matsuda, A. J. Org. Chem. 1998, 63, 1986-1994.
7. Fukuoka, M.; Shuto, S.; Minakawa, N.; Ueno, Y.; Matsuda, A. J. Org. Chem. 2000, 65, 5238-5248.
8. Shuto, S.; Fukuoka, M.; Manikowsky, A.; Ueno, Y.; Nakano, T.; Kuroda, R.; Kuroda, H.; Matsuda, A. J. Am. Chem. Soc. 2001, 123, 8750-8759.
9. Walseth, T. F.; Lee, H. C. Biochim. Biophys. Acta 1993, 1178, 235-242.
10. Bailey, V. C.; Sethi, J. K.; Galione, A.; Potter, B. V. L. Chem. Commun. 1997, 695-696.
11. Ashamu, G. A.; Sethi, J. K.; Galione, A.; Potter, B. V. L. Biochemistry 1997, 36, 9509-9617.
12. Galeone, A.; Mayol, L.; Oliviero, G.; Piccialli, G.; Varra, M. Eur. J. Org. Chem, 2002, 4234-4238.
13. Huang, L. J.; Zhao, Y. Y.; Yuan, L.; Min, J. M.; Zhang, L. H. J. Med. Chem. 2002, 45, 5340-5352.
14. Hutchinson, E. J.; Taylor, B. F.; Blackburn, G. M. Chem. Commun. 1997, 1859-1860.
15. Zhang, F. J.; Sih, C. J. Tetrahedron Lett. 1995, 36, 9289-9292.
16. Graeff, R. M.; Walseth, T. F.; Hill, H. K.; Lee, H. C. Biochemistry 1996, 35, 379-386.
17. Wagner, G. K.; Black, S.; Guse, A. H.; Potter, B. V. L. Chem. Commun. 2003, 1944-1945.
18. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: Berlin, 1984.
19. Schuber, F.; Lund, F. E. Curr. Mol. Med. 2004, 4, 249-261.
20. Schnackerz, K. D.; Vu, C. Q.; Gani, D.; AlvarezGonzalez, R.; Jacobson, M. K. Bioorg. Med. Chem. Lett. 1997, 7, 581-586.
21. Love, M. L.; Szebenyi, D. M. E.; Kriksunov, I. A.; Thiel, D. J.; Munshi, C.; Graeff, R.; Lee, H. C.; Hao, Q. Structure 2004, 12, 477-486.
22. Yamamoto-Katayama, S.; Ariyoshi, M.; Ishihara, K.; Hirano, T.; Jingami, H.; Morikawa, K. J. Mol. Biol. 2002, 316, 711-723.
23. Chenon, M. T.; Pugmire, R. J.; Grant, D. M.; Panzica, R. P.; Townsend, L. B. J. Am. Chem. Soc. 1975, 97, 4636-4642.
24. BIOLOG GmbH, Bremen, Germany.
25. Ikemoto, T.; Haze, A.; Hatano, H.; Kitamoto, Y.; Ishida, M.; Nara, K. Chem. Pharm. Bull. 1995, 43, 210-215.
26. Huang, L. J.; Zhao, Y. Y.; Yuan, L.; Min, J. M.; Zhang, L. H. Bioorg. Med. Chem. Lett. 2002, 12, 887-889.
27. Roelen, H.; Veldman, N.; Spek, A. L.; Kunzel, J. V. D.; Mathot, R. A. A.; Ijzerman, A. P. J. Med. Chem. 1996, 39, 1463-1471.
28. Wlassoff, W. A.; Dobrikov, M. I.; Safronov, I. V.; Dudko, R. Y.; Bogachev, V. S.; Kandaurova, V. V.; Shishkin, G. V.; Dymshits, G. M.; Lavrik, O. I. Bioconjugate Chem. 1995, 6, 352-360.
29. Lee, J.; Churchil, H.; Choi, W. B.; Lynch, J. E.; Roberts, F. E.; Volante, R. P.; Reider, P. J. Chem. Commun. 1999, 729-730.
30. Moffatt, J. G.; Khorana, H. G. J. Am. Chem. Soc. 1961, 83, 649-658.
31. Mukaiyama, T.; Hashimoto, M. Bull. Chem. Soc. Jpn. 1971, 44, 2284.
32. Prabahar, K. J.; Cole, T. D.; Ferris, J. P. J. Am. Chem. Soc. 1994, 116, 10914-10920.
33. Imai, J.; Torrence, P. F. J. Org. Chem. 1985, 50, 1418-1426.
34. Mukaiyama, T.; Matsueda, R.; Suzuki, M. Tetrahedron Lett. 1970, 1901-1904.
35. We find that the turnover rate for this enzymatic conversion considerably depends on the individual batch of commercially available Aplysia californica ADPRC, with reaction times varying from 8 to 48 h.
36. Aritomo, K.; Urashima, C.; Wada, T.; Sekine, M. Nucleosides Nucleotides 1996, 15, 1-16.
37. Amann, N.; Wagenknecht, H. A. Synlett 2002, 687-691.
38. Western, E. C.; Daft, J. R.; Johnson, E. M.; Gannett, P. M.; Shaughnessy, K. H. J. Org. Chem. 2003, 68, 6767-6774.
39. Pathak, T. Chem. Rev. 2002, 102, 1623-1667.
40. Buenger, G. S.; Nair, V. Synthesis 1990, 962-966.
41. Temple, C.; Kussner, C. L.; Montgomery, J. A. J. Org. Chem. 1966, 31, 2210-2215.
42. Temple, C.; Thorpe, M. C.; Coburn, W. C.; Montgomery, J. A. J. Org. Chem. 1966, 31, 935-938.
43. Shuto, S.; Fukuoka, M.; Kudoh, T.; Garnham, C.; Galione, A.; Potter, B. V. L.; Matsuda, A. J. Med. Chem. 2003, 46, 4741-4749.
44. Gu, X. F.; Yang, Z.; Zhang, L.; Kunerth, S.; Fliegert, R.; Weber, K.; Guse, A. H. J. Med. Chem. 2004, 47, 5674-5682.
45. Cartwright, I. L.; Hutchinson, D. W.; Armstrong, V. W. Nucleic Acids Res. 1976, 3, 2331-2339.
46. Guse, A. H.; Cakir-Kiefer, C.; Fukuoka, M.; Shuto, S.; Weber, K.; Bailey, V. C.; Matsuda, A.; Mayr, G. W.; Oppenheimer, N.; Schuber, F.; Potter, B. V. L. Biochemistry 2002, 41, 6744-6751.
47. Guse, A. H.; Roth, E.; Emmrich, F. Biochem. J. 1993, 291, 447-451.
48. Guse, A. H.; da Silva, C. P.; Emmrich, P.; Ashamu, G. A.; Potter, B. V. L.; Mayr, G. W. J. Immunol 1995, 155, 3353-3359.
49. CSA, CSB: Chromatographic system A/B. For details cf. the general Experimental Section in the Supporting Information.
50. Skibo, E. B.; Meyer, R. B. J. Med. Chem. 1981, 24, 1155-1161.