Chemoenzymatic synthesis of 7-deaza cyclic adenosine 5′-diphosphate ribose analogues, membrane-permeant modulators of intracellular calcium release

Journal of Organic Chemistry

Volumn 73, Issue 5, 2008, Pages 1693-1703

  Zhang, Bo ^a   Bailey, Victoria C ^a   Potter, Barry V L ^a  

^a University of Bath   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOENZYMATIC SYNTHESIS; INTRACELLULAR CALCIUM RELEASE;

CALCIUM; ENZYME ACTIVITY; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS (CHEMICAL);

MEMBRANES;

7 DEAZA 8 BROMO CYCLIC ADENOSINE 5' DIPHOSPHATE RIBOSE; CD38 ANTIGEN; CYCLIC ADENOSINE DIPHOSPHATE RIBOSE; CYCLIC DEAZA 2' DEOXYADENOSINE 5' DIPHOSPHATE RIBOSE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CALCIUM TRANSPORT; CARBON NUCLEAR MAGNETIC RESONANCE; CELL MEMBRANE PERMEABILITY; DRUG CONFORMATION; DRUG SYNTHESIS; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE;

CALCIUM; CELL MEMBRANE PERMEABILITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIC ADP-RIBOSE; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR CONFORMATION;

EID: 41149095126     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071236p     Document Type: Article

References (55)

1. Galione, A.; Lee, H. C.; Busa, W. Science 1991, 253, 1143-1146.
2. Koshiyama, H.; Lee, H. C.; Tashjian, A. H. J. Biol. Chem. 1991, 266, 16985-16988.
3. Takasawa, S.; Nata, K.; Yonekura, H.; Okamoto, H. Science 1993, 259, 370-373.
4. Clapper, D. L.; Walseth, T. F.; Dargie, P. J.; Lee, H. C. J. Biol. Chem. 1987, 262, 9561-9568.
5. Dargie, P. J.; Agre, M. C.; Lee, H. C. Cell Regul. 1990, 279-290.
6. Guse, A. H. FEBS 2005, 272, 4590-4597.
7. Lee, H. C.; Aarhus, R. Cell Regul. 1991, 2, 203-209.
8. Walseth, T. F.; Lee, H. C. Biochem. Biophys. Acta 1993, 1178, 235-242.
9. Prasad, G. S.; McRee, D. E.; Stura, E. A.; Levitt, D. G.; Lee, H. C.; Stout, C. D. Nat. Struct. Biol. 1996, 3, 957-963.
10. 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.
11. Zhang, B.; Muller-Steffner, H.; Schuber, F.; Potter, B. V. L. Biochemistry 2007, 46, 4100-4109.
12. Potter, B. V. L.; Walseth, T. F. Curr. Mol. Med. 2004, 4, 303-311.
13. Guse, A. H. Curr. Med. Chem. 2004, 11, 847-855.
14. Wagner, G. K.; Guse, A. H.; Potter, B. V. L. J. Org. Chem. 2005, 70, 4810-4819.
15. Moreau, C.; Wagner, G. K.; Weber, K.; Guse, A. H.; Potter, B. V. L. J. Med. Chem. 2006, 49, 5162-5176.
16. Liu, Q.; Kriksunov, I. A.; Moreau, C.; Graeff, R.; Potter, B. V. L.; Lee, H. C.; Hao, Q. J. Biol. Chem. 2007, 282, 24825-24832.
17. Shuto, S.; Fukuoka, M.; Kudoh, T.; Garnham, C.; Gallone, A.; Potter, B. V. L.; Matsuda, A. J. Med. Chem. 2003, 46, 4741-47490.
18. Kudoh, T.; Fukuoka, M.; Ichikawa, S.; Murayama, T.; Ogawa, Y.; Hashii, M.; Higashida, H.; Kunerth, S.; Weber, K.; Guse, A. H.; Potter, B. V. L.; Matsuda, A.; Shuto, S. J. Am. Chem. Soc. 2005, 127, 8846-8855.
19. Bailey, V. C.; Fortt, S. M.; Summerhill, R. J.; Gallone, A.; Potter, B. V. L. FEBS Lett. 1996, 379, 227-230.
20. Gu, X. F.; Yang, Z.; Zhang, L.; Kunerth, S.; Fliegert, R.; Weber, K.; Guse, A. H.; Zhang, L. J. Med. Chem. 2004, 47, 5674-5682.
21. Guse, A. H.; Gu, X.; Zhang, L.; Weber, K.; Kramer, E.; Yang, Z.; Jin, H.; Li, Q.; Carrier, L.; Zhang, L. J. Biol. Chem. 2005, 280, 15952-15959.
22. Bailey, V. C.; Sethi, J. K.; Fortt, S. M.; Galione, A.; Potter, B. V. L. Chem. Biol. 1997, 4, 51-61.
23. Sethi, J. K.; Empson, R. M.; Bailey, V. C.; Potter, B. V. L.; Galione, A. J. Biol. Chem. 1997, 272, 16358-16363.
24. Bailey, V. C.; Sethi, J. K.; Galione, A.; Potter, B. V. L. Chem. Commun. 1997, 695-696.
25. Guse, A. H.; da Silva, C. P.; Berg, I.; Skapenko, A. L.; Weber, K.; Heyer, P.; Hohenegger, M.; Ashamu, G. A.; Schulze-Koops, H.; Potter, B. V. L.; Mayr, G. W. Nature 1999, 398, 70-73.
26. Reyes-Harde, M.; Empson, R.; Potter, B. V. L.; Galione, A.; Stanton, P. K. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4061-40660.
27. Shuto, S.; Matsuda, A. Curr. Med. Chem. 2004, 11, 827-845.
28. Ashamu, G. A.; Galione, A.; Potter, B. V. L. J. Chem. Soc. Chem. Commun. 1995, 1359-1360.
29. Prabahar, K. J.; Cole, T. D.; Ferris, J. P. J. Am. Chem. Soc. 1994, 116, 10914-10920.
30. Lee, J.; Churchill, H.; Choi, W. B.; Lynch, J. E.; Roberts, F. E.; Volante, R. P.; Reider, P. J. Chem. Commun. 1999, 729-730.
31. Bergstrom, D. E.; Brattesani, A. J. Nucleic Acids Res. 1980, 8, 6213-6219.
32. Mitchell, R. H.; Lai, Y. H.; Williams, R. V. J. Org. Chem. 1979, 44, 4733-4735.
33. Ikehara, M.; Uesugi, S.; Yoshida, K. Biochemistry 1972, 11, 830-836.
34. Sarma, R. H.; Lee, H. C.; Evans, F. E.; Yathindra, N.; Sundaralingam, M. J. Am. Chem. Soc. 1974, 96, 7337-7348.
35. Ikemoto, T.; Haze, A.; Hatano, H.; Kitamoto, Y.; Ishida, M.; Nara, K. Chem. Pharm. Bull. 1995, 43, 210-215.
36. Hughes, N. H.; Kenner, G. W.; Todd, J. Chem. Soc. 1957, 3733-3736.
37. Wang, L.; Aarhus, R.; Lee, H. C.; Walseth, T. F. Biochim. Biophys. Acta 1999, 1472, 555-564.
38. Walseth, T. F.; Aarhus, R.; Gurnack, M. E.; Wong, L.; Breitinger, H. G.; Gee, K. R.; Lee, H. C. Methods Enzymol. 1997, 280, 294-305.
39. Moffatt, J. G.; Khorana, H. G. J. Am. Chem. Soc. 1961, 83, 649-658.
40. Lee, H. C.; Aarhus, R.; Levitt, D. Nat. Struct. Biol. 1994, 1, 143-144.
41. Ashamu, G. A.; Sethi, J. K.; Galione, A.; Potter, B. V. L. Biochemistry 1997, 36, 9509-9517.
42. Seela, F.; Muth, H.-P.; Bindig, U. Synthesis 1988, 670-674.
43. Tsytovich, A. V.; Shamshin, D. V.; Burkovskii, V. B.; Shvets, V. I. Russ. J. Bioorg. Chem. 1995, 21, 756-761.
44. Hoffer, M. Chem. Ber. 1960, 93, 2777-2780.
45. Hotoda, H.; Murayama, K.; Miyamoto, S.; Iwata, Y.; Takahashi, M.; Kawase, Y.; Tanzawa, K.; Kaneko, M. Biochemistry 1999, 38, 9234-9241.
46. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333-2344.
47. Birdsall, B.; Birdsall, N. J. M.; Feeney, J.; Thornton, J. J. Am. Chem. Soc. 1975, 97, 2845-2850.
48. Graham, S. M.; Macaya, D. J.; Sengupta, R. N.; Turner, K. B. Org. Lett. 2004, 6, 233-236.
49. Wada, T.; Inageda, K.; Aritomo, K.; Tokita, K.; Nishina, H.; Takahashi, K.; Katada, T.; Sekine, M. Nucleosides Nucleotides 1995, 14, 1301-1314.
50. Zhang, B.; Wagner, G.; Weber, K.; Garnham, C.; Morgan, A. J.; Galione, A.; Guse, A. H.; Potter, B. V. L. J. Med. Chem. 2008, in press.
51. Garrett, E. R.; Mehta, P. J. J. Am. Chem. Soc. 1972, 94, 8532-8540.
52. Moreau, C.; Woodman, T. J.; Potter, B. V. L. Chem. Commum. 2006, 1127-1129.
53. Johnson, R. W.; Marschner, T. M.; Oppenheimer, N. J. J. Am. Chem. Soc. 1988, 110, 2257-2263.
54. Kaplan, N. O.; Colowick, S. P.; Barnes, C. C. J. Biol. Chem. 1951, 191, 461-472.
55. Graeff, R.; Munshi, C.; Aarhus, R.; John, M.; Lee, H. C. J. Biol. Chem. 2001, 276, 12169-12173.