13C-1H and 13C-13C spin couplings in [2'-13C]2'-deoxyribonucleosides: Correlations with molecular structure

Journal of the American Chemical Society

Volumn 119, Issue 7, 1997, Pages 1737-1744

  Bandyopadhyay, Tapasree ^a   Wu, Jian ^b   Stripe, Wayne A ^a   Carmichael, Ian ^c   Serianni, Anthony S ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b University of Texas Medical Branch School of Medicine   (United States)

^c UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 13; DEOXYRIBONUCLEOSIDE;

ARTICLE; DNA STRUCTURE; DRUG STRUCTURE; ISOTOPE LABELING; NUCLEAR MAGNETIC RESONANCE;

EID: 0030974046     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961622g     Document Type: Article

References (67)

1. Fesik, S. W.; Zuiderweg, E. R. P. Q. Rev. Biophys. 1990, 23, 97-131.
2. (a) Bodenhausen, G.; Ruben, D. J. Chem. Phys. Lett. 1980, 69, 185-189.
3. (b) Bax, A.; Griffey, R. H.; Hawkins, B. L. J. Magn. Reson. 1983, 55, 301.
4. (c) Müller, L. J. Am. Chem. Soc. 1979, 101, 4481-4484.
5. (d) Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093-2094.
6. (a) Kay, L. E.; Torchia, D.; Bax, A. Biochemistry 1989, 28, 8972-8979.
7. (b) Peng, J. W.; Wagner, G. J. Magn. Reson. 1992, 98, 308-332.
8. (c) Nirmala, N. R.; Wagner, G. J. Am. Chem. Soc. 1988, 110, 7557-7558.
9. (d) Kay, L. E.; Bull, T. E.; Nicholson, L. K.; Griesinger, C.; Schwalbe, H.; Bax, A.; Torchia, D. A. J. Magn. Reson. 1992, 100, 538-558.
10. Biamonti, C.; Rios, C. B.; Lyons, B. A.; Montelione, G. T. Adv. Biophys. Chem. 1994, 4, 51-120.
11. (a) Fesik, S. W.; Zuiderweg, E. R. P. J. Magn. Reson. 1988, 78, 588-593.
12. (b) Marion, D.; Kay, L. E.; Sparks, S. W.; Torchia, D. A.; Bax, A. J. Am. Chem. Soc: 1989, 111, 1515-1517.
13. Wüthrich, K. NMR of Proteins and Nucleic Acids, J. Wiley and Sons: New York, 1986.
14. Muchmore, D. C.; McIntosh, L. P.; Russell, C. B.; Anderson, D. E.; Dahlquist, F. W. Methods Enzymol. 1989, 177, 44-73.
15. (a) Nikonowicz, E. P.; Sirr, A.; Legault, P.; Jucker, F. M.; Baer, L. M.; Pardi, A. Nucl. Acids Res. 1992, 20, 4507-4513.
16. (b) Lancelot, G.; Chanteloup, L.; Beau, J.-M.; Thuong, N. T. J. Am. Chem. Soc. 1993, 115, 1599-1600.
17. (c) Michnicka, M. J.; Harper. J. W.; King, G. C. Biochemistry 1993, 32, 395-400.
18. (d) Tate, S.; Ono, A.; Kainosho, M. J. Am. Chem. Soc. 1994, 116, 5977-5978.
19. (e) Wu, J.; Serianni, A. S. Biopolymers 1994, 34, 1175-1186.
20. (f) SantaLucia, J., Jr.; Shen, L. X.; Cai, Z.; Lewis, H.; Tinoco, I., Jr. Nucl. Acids Res. 1995, 23, 4913-4921.
21. (a) Bandyopadhyay, T.; Wu, J.; Serianni, A. S. J. Org. Chem. 1993, 58, 5513-5517.
22. (b) Kline, P. C.; Serianni, A. S. Magn. Reson. Chem. 1990, 28, 324-330.
23. Kline, P. C.; Serianni, A. S. J. Am. Chem. Soc. 1990, 112, 7373-7381.
24. Robins, M. J.; Wilson, J. S.; Hansske, F. J. Am. Chem. Soc. 1983, 105, 4059-4065.
25. Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234-1255.
26. (a) Braunschweiler, L.; Ernst, R. R. J. Magn. Reson. 1983, 53, 521-528.
27. (b) Serianni, A. S.; Podlasek, C. A. Carbohydr. Res. 1994, 259, 277-282.
28. (c) Wu, J.; Serianni, A. S. Carbohydr. Res. 1992, 226, 209-219.
29. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzales, C.; Martin, R. L.; Fox, D. J.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92, Revision C.3; Gaussian, Inc.: Pittsburgh, PA, 1992.
30. (a) Podlasek, C. A.; Stripe, W. A.; Carmichael, I.; Shang, M.; Basu, B.; Serianni, A. S. J. Am. Chem. Soc. 1996, 118, 1413-1425.
31. (b) Serianni, A. S.; Chipman, D. M. J. Am. Chem. Soc. 1987, 109, 5297-5303.
32. (a) Serianni, A. S.; Wu, J.; Carmichael, I. J. Am. Chem. Soc. 1995, 117, 8645-8650.
33. (b) Kowalewski, J.; Laaksonen, A.; Roos, B.; Siegbahn, P. J. Chem. Phys. 1979, 71, 2896-2902.
34. Carmichael, I. J. Phys. Chem. 1993, 97, 1789-1792.
35. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8205-8212.
36. Jardetzky, O. Biochim. Biophys. Acta 1980, 621, 227-232.
37. Saenger, W. Principles of Nucleic Acid Structure, Springer-Verlag: New York, 1984, p 61.
38. (a) PSEUROT 6.2, Gorlaeus Laboratories, University of Leiden.
39. (b) de Leeuw, F. A. A. M.; Altona, C. J. Comp. Chem. 1983, 4, 428-437.
40. (c) Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; de Leeuw, H. P. M.; Altona, C. Org. Magn. Reson. 1981, 15, 43-52.
41. (a) Davies, D. B.; Danyluk, S. S. Biochemistry 1974, 13, 4417-4434.
42. (b) Rinkel, L. J.; Altona, C. J. Biomol. Struct. Dyn. 1987, 4, 621-649.
43. 18
44. Serianni, A. S. In NMR of Biological Macromolecules; Stassinopoulou, C., Ed.; NATO ASI Series H: Cell Biology; Springer-Verlag; New York, 1994; Vol. 87, pp 293-306.
45. (a) Davies, D. B.; MacCoss, M.; Danyluk, S. S. J. Chem. Soc., Chem. Commun. 1984, 536-538.
46. (b) Davies, D. B.; Rajani, P.; Sadikot, H. J. Chem. Soc., Perkin Trans. 2 1985, 279-285.
47. (c) Bock, K.; Pedersen, C. Acta Chem. Scand. Ser. B 1977, B31, 354-358.
48. Podlasek, C. A.; Wu, J.; Stripe, W. A.; Bondo, P. B.; Serianni, A. S. J. Am. Chem. Soc. 1995, 117, 8635-8644.
49. Walker, T. E.; London, R. E.; Barker, R.; Matwiyoff, N. A. Carbohydr. Res. 1978, 60, 9-18.
50. Serianni, A. S.; Barker, R. J. Org. Chem. 1984, 49, 3292-3300.
51. (a) Kline, P. C; Serianni, A. S. J. Org. Chem. 1992, 57, 1772-1777.
52. (b) Lemieux, R. U. Pure Appl. Chem. 1971, 25, 527-548.
53. Duker, J. M.; Serianni, A. S. Carbohydr. Res. 1993, 249, 281-303.
54. Carmichael, I.; Chipman, D. M.; Podlasek, C. A.; Serianni, A. S. J. Am. Chem. Soc. 1993, 115, 10863-10870.
55. Marshall, J. L. Carbon-Carbon and Carbon-Proton NMR Couplings: Applications to Organic Stereochemistry and Conformational Analysis, Methods in Stereochemical Analysis; Verlag Chemie International, Deerfield Beach, FL, 1983; Vol. 2, pp 186-193.
56. King-Morris, M. J.; Serianni, A. S. J. Am. Chem. Soc. 1987, 109, 3501-3508.
57. (a) Wu, J.; Bondo, P. B.; Vuorinen, T.; Serianni, A. S. J. Am. Chem. Soc. 1992, 114, 3499-3505.
58. (b) Church, T.; Serianni, A. S. Carbohydr. Res. 1996, 280, 177-186.
59. Serianni, A. S.; Bondo, P. B.; Zajicek, J. J. Magn. Reson. Ser. B 1996, 112, 69-74.
60. Hines, J. V.; Landry, S. M.; Varani, G.; Tinoco, I., Jr. J. Am. Chem. Soc. 1994, 116, 5823-5831.
61. Marino, J. P.; Schwalbe, H.; Glaser, S. J.; Griesinger. C. J. Am. Chem. Soc. 1996, 118, 4388-4395.
62. (a) Grzesiek, S.; Vuister, G. W.; Bax, A. J. Biomol. NMR 1993, 3, 487-493.
63. (b) Bax, A.; Max, D.; Zax, D. J. Am. Chem. Soc. 1994, 114, 6924-6925.
64. Hu, J.-S.; Bax, A. J. Am. Chem. Soc. 1996, 118, 8170-8171.
65. (a) Schwarcz, J. A.; Perlin, A. S. Can. J. Chem. 1972, 50, 3667-3676.
66. (b) Spoormaker, T.; de Bie, M. J. A. Recl. Trav. Chim. Pays-Bas 1978, 97, 85-87.
67. Krivdin, L. B.; Kalabin, G. A. Prog. NMR Spectrosc. 1989, 21, 293-448.