The quantitation of the competing energetics of the stereoelectronic and steric effects of the 3'-OH and the aglycone in the α- versus β-D- and -L- 2'-deoxyribonucleosides by 1H-NMR

Tetrahedron

Volumn 54, Issue 9, 1998, Pages 1867-1900

  Thibaudeau, Christophe ^a   Földesi, András ^a   Chattopadhyaya, Jyoti ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; DEOXYRIBONUCLEOSIDE; PROTON;

ARTICLE; CONFORMATION; ENERGY TRANSFER; PKA; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOSPECIFICITY;

EID: 0032567873     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10403-3     Document Type: Article

References (75)

1. 1. Thibaudeau, C.; Földesi; A; Chattopadhyaya, J. Tetrahedron 1997, 53, 14043.
2. 2. Thibaudeau, C.; Plavec, J.; Chattopadhyaya, J. J. Org. Chem. 1996, 61, 266.
3. 3. (a) Urata, H.; Ogura, E.; Shinohara, K.; Ueda, Y.; Akagi, M. J. Am. Chem. Soc. 1991, 113, 8174.
4. (b) Doi, M.; Inoue, M.; Tomoo, K.; Ishida, T.; Ueda, Y.; Akagi, M. ; Urata, H. J. Am. Chem. Soc. 1993, 115, 10432.
5. 4. Jyoce, G.F.; Visser, G.M.; van Boeckel, C.A.A.; van Boom, J.H.; Orgel, L.E.; van Westrenen, J. Nature 1984, 310, 602.
6. 5. Kaplan, N.O.; Ciotti, M.M.; Stolzenbach, F.E.; Bachur, N.R. J. Am. Chem. Soc. 1955, 77, 813.
7. 6. (a) Suzuki, S.; Suzuki, K.; Imai, T.; Suzuki, N.; Okuda, S. J. Biol. Chem. 1965, 240 , 554.
8. (b) Suzuki, K.; Nakano, H.; Suzuki, S. J. Biol. Chem. 1967, 242, 3319.
9. 7. Dinglinger, F.; Renz, P. Hoppe-Seyler's Z. physiol. Chem. 1971, 362, 1157.
10. 8. (a) LePage, G.A.; Junga, I.G. Mol. Pharmacol. 1967, 2, 37.
11. (b) LePage, G.A. Can. J. Biochem. 1968, 46, 655.
12. (c) Perry, A.; LePage, G.A. Cancer Res. 1969, 29, 617.
13. (d) Nakai, Y.; LePage, G.A. Cancer Res. 1972, 32, 2445.
14. (e) Tamaoki, T.; LePage, G.A. Cancer Res. 1975, 35, 1015.
15. 9. Bobek, M.; Bloch, A. J. Med. Chem. 1975, 18, 784.
16. 10. Falke, D.; Range, K.; Arendes, J.; Müller, W.E.G. Biochim. Biophys. Acta 1979, 563, 36.
17. 11. Christensen, L.F.; Broom, A.D.; Robins, M.J.; Bloch, A. J. Med. Chem. 1972, 15, 735.
18. 12. Séquin, U. Experientia 1973, 29, 1059.
19. 13. (a) Morvan, F.; Rayner, B.; Imbach, J.-L.; Chang, D.-K.; Lown, J.W. Nucleic Acids Res. 1987, 75, 4241.
20. (b) Morvan, F.; Rayner, B.; Imbach, J.-L.; Lee, M.; Hartley, J.A.; Chang, D.-K.; Lown J.W. Nucleic Acids Res. 1987, 15, 7027.
21. 14. (a) Kilpatrick, J.E.; Pitzer, K.S. ; Spitzer, R. J. Am. Chem. Soc. 1947, 69, 2483.
22. (b) Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8205.
23. (c) Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333.
24. 15. (a) de Leeuw, H.P.M; Haasnoot, C.A.G. ; Altona, C. Isr. J. Chem. 1980, 20, 108.
25. (b) Altona, C.; Francke, R.; de Haan, R.; Ippel, J.H.; Daalmans, G.J.; Westra Hoekzema, A.J.A.; van Wijk, J. Magn. Res.on Chem. 1994, 32, 670.
26. 16. (a) Feigon, J.; Wang, A. H. -J.; van der Marel, G. A.; van Boom, J. H.; Rich, A. Nucleic Acids Res. 1984, 12, 1243.
27. (b) Tran-Dinh, S.; Taboury, J.; Neumann, J. -M.; Huynh-Dinh, T.; Genissel, B.; Laglois d'Estaintot, B.; Igolen, J. Biochemistry 1984, 23, 1362.
28. 17. (a) Davis, P. W.; Hall, K.; Cruz, P.; Tinoco, I.; Neilson, T. Nucleic Acids Res. 1986, 14, 1279.
29. (b) Davis, P. W.; Adamiak, R. W.; Tinoco, I. Biopolymers 1990, 29, 109.
30. 18. (a) Agback, P.; Sandstrom, A.; Yamakage, S. -I.; Sund, C.; Glemarec, C.; Chattopadhyaya, J. J. Biochem. Biophys. Methods 1993, 27, 229.
31. (b) Agback, P.; Glemarec, C.; Yin, L.; Sandstrom, A.; Plavec, J.; Sund, C.; Yamakage, S. -I.; Wiswanadham, G.; Rousse, B.; Puri, N.; Chattopadhyaya, J. Tetrahedron Lett. 1993, 34, 3929.
32. 19. Izatt, R. M.; Christensen, J.J .; Rytting, J. H. Chem. Rev. 1971, 71, 439.
33. 20. Hoffmann, R.A.; van Wijk, J.; Leeflang, B.R.; Kamerling, J.P.; Altona, C.; Vliegenthart, J.F.G. J. Am. Chem. Soc., 1992, 114, 3710.
34. 21. (a) Plavec, J.; Tong, W.; Chattopadhyaya, J. J. Am. Chem. Soc. 1993, 115, 9734.
35. (b) Plavec, J.; Garg, N.; Chattopadhyaya, J. J. Chem. Soc., Chem. Commun. 1993, 1011.
36. (c) Plavec, J.; Koole, L. H.; Chattopadhyaya, J. J. Biochem. Biophys. Meth. 1992, 25, 253.
37. (d) Koole. L. H.; Buck, H. M.; Nyilas, A.; Chattopadhyaya, J. Can J. Chem. 1987, 65, 2089.
38. (e) Koole, L. H.; Buck, H. M.; Bazin, H.; Chattopadhyaya, J. Tetrahedron 1987, 43, 2289.
39. (f) Koole, L. H.; Plavec, J.; Liu, H.; Vincent, B. R.; Dyson, M. R.; Coe, P. L.; Walker, R. T.; Hardy, G. W.; Rahim, S. G.; Chattopadhyaya J. J. Am. Chem. Soc. 1992, 114, 9934.
40. (g) Plavec, J.; Thibaudeau, C.; Viswanadham, G.; Sund, C.; Chattopadhyaya, J. J. Chem. Soc., Chem. Commun. 1994, 781.
41. (h) Thibaudeau, C.; Plavec, J.; Watanabe, K. A.; Chattopadhyaya, J. J. Chem. Soc., Chem. Commun. 1994, 537.
42. (i) Thibaudeau, C.; Plavec, J.; Garg, N.; Papchikhin, A.; Chattopadhyaya, J. J. Am. Chem. Soc. 1994, 116, 4038.
43. (j) Plavec, J.; Thibaudeau, C.; Chattopadhyaya, J. J. Am. Chem. Soc. 1994, 116, 6558.
44. (k) Thibaudeau, C.; Plavec, J.; Chattopadhyaya, J. J. Am. Chem. Soc. 1994, 116, 8033.
45. (l) Plavec, J.; Thibaudeau, C; Chattopadhyaya, J. Tetrahedron 1995, 51, 11775.
46. (m) Plavec, J.; Thibaudeau, C.; Chattopadhyaya, J. in How do the Energetics of the Stereoelectronic Gauche and Anomeric Effects Modulate the Conformation of Nucleos(t)ides ?, International Union of Pure and Applied Chemistry, 1996, in press.
47. 22. (a) De Leeuw, F. A. A. M. and Altona, C. J. Comp. Chem. 1983, 4, 428 and PSEUROT, QCPE program No 463.
48. (b) Diez, E.; Fabian, J. S.; Guilleme, J.; Altona, C. and Donders, L.A. Mol. Phys. 1989, 68, 49.
49. (c) Donders, L. A.; de Leeuw, F. A. A. M. and Altona, C. Magn. Reson. Chem. 1989, 27, 556.
50. (d) Altona, C.; Ippel, J.H.; Hoekzema, A. J. A. W.; Erkelens, C.; Groesbeek, G.; Donders, L.A. Magn. Reson. Chem. 1989, 27, 564.
51. (e) Van Wijk, J., unpublished result.
52. 23. Edward, J.T. Chem. Ind. (London) 1955, 1102.
53. 24. For review articles on the anomeric effect, see: (a) Tvaroska, I.; Bleha, T. Adv. Carbohydr. Chem. 1989, 47, 45.
54. (b) Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019.
55. (c) Petillo, P. A.; Lerner, L. A. in The Anomeric Effect and Associated Stereolectronic Effects, Thatcher, G. R .J. Ed., ACS Symposium Series: Washington, DC, 1993, pp. 156.
56. (d) Box, V. G. S. Heterocycles 1990, 31, 1157.
57. 25. (a) Lucken, E. A. C. J. Chem. Soc. 1959, 2954.
58. (b) Romers, C.; Altona, C; Buys, H. R.; Havinga, E. Top. Stereochem. 1969, 4, 39.
59. (c) Perrin, C. L.; Armstrong, K. B.; Fabian, M. A. J. Am. Chem. Soc. 1994, 116, 715.
60. (d) Salzner, U. J. Org. Chem. 1995, 60, 986.
61. (e) Cosse-Barbi, A.; Watson, D. G.; Dubois, J. E. Tetrahedron Lett. 1989, 30, 163.
62. 26. (a) Olson, W.K.; Sussman, J. L. J. Am. Chem. Soc. 1982, 104, 270.
63. (b) Olson, W.K. J. Am. Chem. Soc. 1982, 104, 278.
64. (c) Phillips, L.; Wray, V. J. Chem. Soc., Chem. Commun. 1973, 90.
65. (d) Brunck, T.K.; Weinhold, F. J. Am. Chem. Soc. 1979, 101, 1700.
66. (e) Murcko, M.A.; DiPaola, R.A. J. Am. Chem. Soc. 1992, 114, 10010.
67. (f) Wiberg, K.B.; Murcko, M.A.; Laidig, K.E.; MacDougall, P.J. J. Phys. Chem. 1990, 94, 6956.
68. 27. Rosemeyer, H.; Tóth, G.; Golankiewicz, B.; Kazimierczuk, Z.; Bourgeois, W.; Kretschmer, U.; Muth, H.-P. and Seela, F. J. Org. Chem. 1990, 55, 5784.
69. 28. (a) Lee, T.D.; Yang, C.N. Phys. Rev. 1956, 104, 254.
70. (b) Quack, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 571.
71. (c) Mason, S.F. Chirality, 1991, 3, 223.
72. (d) Tranter, G.E. Nature, 1985, 318, 172.
73. (e) Tranter, G.E. Chem. Phys. Lett. 1987, 135, 279.
74. (f) Kondepudi, D.K.; Nelson, G.W.; Nature, 1985, 314, 438.
75. 29. DAISY, Spin Simulation Program, provided by Bruker, was used with 7 spins systems.