HIV-1 reverse transcriptase can discriminate between two conformationally locked carbocyclic AZT triphosphate analogues

Journal of the American Chemical Society

Volumn 120, Issue 12, 1998, Pages 2780-2789

  Marquez, Victor E ^a   Ezzitouni, Abdallah ^a   Russ, Pamela ^a   Siddiqui, Maqbool A ^a   Ford Jr , Harry ^a   Feldman, Ron J ^a   Mitsuya, Hiroaki ^a   George, Clifford ^b   Barchi Jr , Joseph J ^a  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RNA DIRECTED DNA POLYMERASE;

ANTIVIRAL ACTIVITY; ARTICLE; CONFORMATIONAL TRANSITION; ENZYME BINDING; ENZYME CONFORMATION; ENZYME INHIBITION; GENE TARGETING; GLYCOSYLATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 0032054586     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973535+     Document Type: Article

References (56)

1. (a) For a recent review on the use of anti-HIV nucleosides, see: Anti-HIV Nucleosides: Past, Present and Future; Mitsuya, H., Ed.; R. G. Landes Co.: 810 S. Church St., Georgetown, TX, 1997.
2. (b) Luzuriaga, K.; Bryson, Y.; Krogstad, P.; Robinson, J.; Stechenberg, B.; Lamson, M.; Cort, S.; Sullivan, J. L. New Engl. J. Med. 1997, 336, 1343.
3. (c) Perelson, A. S.; Essunger, P.; Cao, Y.; Vesanen M.; Hurley, A.; Saksela, K.; Markowitz, M.; Ho, D. D. Nature 1997, 387, 188.
4. (a) Van Roey, P.; Salerno, J. J.; Duax, W. L.; Chu, C. K.; Ahn, M. K.; Schinazi, R. F. J. Am. Chem. Soc. 1988, 110, 2277.
5. (b) Van Roey, P.; Salerno, J. M.; Chu, C. K.; Schinazi, R. F. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 3929.
6. (a) Altona, C.; Sundaranlingam, M. J. Am. Chem. Soc. 1972, 94, 8205.
7. (b) For a comprehensive review of these concepts, see: Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984.
8. Van Roey, P.; Taylor, E. W.; Chu, C. K.; Schinazi, R. F. Ann. N.Y. Acad. Sci. 1990, 616, 29.
9. Taylor, E. W.; Van Roey, P.; Schinazi, R. F.; Chu, C. K. Antiviral Chem. Chemother. 1990, 1, 163.
10. Plavec, J.; Tong, W.; Chattopadhyaya, J. J. Am. Chem. Soc. 1993, 115, 9734.
11. DeLeeuw, H. P. M.; Haasnoot, C. A. G.; Altona, C. Isr. J. Chem. 1980 20, 108.
12. (a) Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Barchi, J. J., Jr. Tetrahedron Lett. 1993, 34, 6233.
13. (b) Altmann, K.-H.; Kesselring, R.; Francotte, E.; Rihs, G. Tetrahedron Lett. 1994, 35, 2331.
14. (c) Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Mitsuya, H.; Barchi, J. J., Jr. J. Med. Chem. 1994, 37, 3389.
15. (d) Altmann, K.-H.; Imwinkelried, R.; Kesselring, R.; Rihs, G. Tetrahedron Lett. 1994, 35, 7625.
16. (e) Ezzitouni, A.; Barchi, J. J., Jr.; Marquez, V. E. J. Chem. Soc., Chem. Commun. 1995, 1345.
17. (f) Jeong, L. S.; Marquez, V. E.; Yuan, C.-S.; Borchardt, R. T. Heterocycles 1995, 41, 2651.
18. (g) Siddiqui, M. A.; Ford, H., Jr.; George, C.; Marquez, V. E. Nucleosides Nucleotides 1996, 15, 235.
19. (h) Jeong, L. S.; Marquez, V. E. Tetrahedron Lett. 1996, 37, 2353.
20. (i) Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. J. Med. Chem. 1996, 39, 3739.
21. (J) Ezzitouni, A.; Marquez, V. E. J. Chem. Soc., Perkin Trans. 1 1997, 1073.
22. (k) Ezzitouni, A.; Russ, P.; Marquez, V. E. J. Org. Chem. 1997, 62, 4870.
23. The correct numbering system for these compounds must follow the nomenclature for the bicyclo[3.1.0]hexane system. This numbering system is used in the Experimental Section and in the discussion of the chemical synthesis described in the text. However, a nucleoside numbering system, such as the one used in Figures 2 and 4, is utilized when comparing the conformation of these bicyclonucleosides with conventional nucleosides.
24. (a) Lai, T. F.; Marsh, R. E. Acta Crystallogr. B 1972, 28, 1982.
25. (b) Green, E. A.; Rosenstein, R. D.; Shiono, R.; Abraham, D. J.; Trus, B. L.; Marsh, R. E. Acta Crystallogr. B 1975, 31, 102.
26. (c) Tavale, S. S.; Sobell, H. M. J. Mol. Biol. 1970, 48, 109.
27. (d) Suck, D.; Saenger, W. J. Am. Chem. Soc. 1972, 94, 6520.
28. Painter, G. R.; Aulabaugh, A. E.; Andrews, C. W. Biochem. Biophys. Res. Commun. 1993, 191, 1166.
29. (a) Plavec, J.; Koole, L. H.; Sandstrom, A.; Chattopadhyaya, J. Tetrahedron 1991, 47, 7363.
30. (b) Lemieux, R. U.; Nagabhushan, T. L.; Paul, B. Can. J. Chem. 1972, 50, 773.
31. (c) Davies, D. B. Prog. Nucl. Magn. Reson. Spectrosc. 1978, 12, 135.
32. Rahman, A. Nuclear Magnetic Resonance: Basic Principles; Springer-Verlag: New York, 1986.
33. Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783.
34. (a) Majumdar, C.; Abbotts, J.; Broder, S.; Wilson, S. H. J. Biol. Chem. 1988, 263, 15657.
35. (b) Kedar, P. S.; Abbotts, J.; Kovacs, T.; Lesiak, K.; Torrence, P.; Wilson, S. H. Biochemistry 1990, 29, 3603.
36. (c) Reardon, J. E.; Miller, W. H. J. Biol. Chem. 1990, 265, 20302.
37. (d) Kati, W. M.; Johnson, K. A.; Jerva, L. F.; Anderson, K. S. J. Biol. Chem. 1992, 267, 25988.
38. (e) Hsie, J.; Zinnen, S.; Modrich, P. J. Biol. Chem. 1993, 268, 24607.
39. (f) Rittinger, K.; Divita, G.; Goody, R. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 8046.
40. Jacobo-Molina, A.; Ding, J. P.; Nanni, R. G.; Clark, A. D.; Lu, X. D.; Tantillo, C.; Williams, R. L.; Kamer, G.; Ferris, A. L.; Clark, P.; Hizi, A.; Hughes, S. H.; Arnold, E. Proc. Natl Acad. Sci. U.S.A. 1993, 90, 6320.
41. (a) Marquez, V. E.; Lim, M.-I. Med. Res. Rev. 1986, 6, 1.
42. (b) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571.
43. (c) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
44. (d) Marquez, V. E. Carbocyclic nucleosides. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; JAI Press Inc.: Greenwich, CT, 1996; Vol. 2, pp 89-146.
45. (a) Kalman, A.; Koritsanzky, T.; Beres, J.; Sagi, G. Nucleosides Nucleotides 1990, 9, 235.
46. (b) Bodenteich, M.; Griengl, H. Tetrahedron Lett. 1987, 28, 5311.
47. Dijkstra, S.; Benevides, J. M.; Thomas, G. J., Jr. J. Mol. Struct. 1991, 242, 283.
48. (a) Eschenmoser, A.; Dobler, M. Helv. Chim. Acta 1992, 75, 218.
49. (b) Pitsch, S.; Wendeborn, S.; Jaun, B.; Eschenmoser, A. Helv. Chim. Acta 1993, 76, 2161.
50. (c) Otting, G. Billeter, M.; Wuthrich, K.; Roth, H. J.; Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1993, 76, 2701.
51. (d) Schlonvogt, I.; Pitsch, S.; Lesueur, C.; Eschenmoser, A.; Jaun, B.; Wolf, R. M. Helv. Chim. Acta 1996, 79, 2316.
52. Macura, S.; Ernst, R. R. Mol. Phys. 1980, 41, 95.
53. Rance, M.; Sorenson, O. W.; Bodenhausen, G.; Wagner, G.; Ernst, R. R.; Wuthrich, K. Biochem. Biophys. Res. Commun. 1983, 117, 479.
54. Bax, A.; Davis, D. G. J. Magn. Reson. 1985, 65, 355.
55. Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; St. Clair, M. H.; Lehrman, S. N.; Gallo, R. C.; Bolognesi, D.; Barry, D. W.; Broder, S. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7096.
56. Ueno, T.; Shirasaka, T.; Mitsuya, H. J. Biol. Chem. 1995, 270, 23605.