The tunable transmission of the aromatic character of the aglycone through the anomeric effect in C-nucleosides drives its own sugar conformation: A thermodynamic study

Tetrahedron

Volumn 53, Issue 18, 1997, Pages 6433-6464

  Luyten, Ingrid ^a   Thibaudeau, Christophe ^a   Sandström, Anders ^a   Chattopadhyaya, Jyoti ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE;

ARTICLE; CALCULATION; CRYSTAL STRUCTURE; PRIORITY JOURNAL; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0030944463     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00302-5     Document Type: Article

References (65)

1. (a) Plavec, J.; Tong, W.; Chattopadhyaya, J. J. Am. Chem. Soc. 1993, 115, 9734.
2. (b) Plavec, J.; Garg, N.; Chattopadhyaya, J. J. Chem.Soc., Chem. Commun. 1993, 1011.
3. (c) Plavec, J.; Koole, L. H.; Chattopadhyaya, J. J. Biochem. Biophys. Meth. 1992, 25, 253.
4. (d) Koole, L. H.; Buck, H. M.; Nyilas, A.; Chattopadhyaya, J. Can J. Chem. 1987, 65, 2089.
5. (e) Koole, L. H.; Buck, H. M.; Bazin, H.; Chattopadhyaya, J. Tetrahedron 1987, 43, 2289.
6. (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.
7. (g) Plavec, J.; Thibaudeau, C.; Viswanadham, G.; Sund, C.; Chattopadhyaya, J. J. Chem. Soc., Chem. Comm. 1994, 781.
8. (h) Thibaudeau, C.; Plavec, J.; Watanabe, K. A.; Chattopadhyaya, J. J. Chem. Soc., Chem. Comm. 1994, 537.
9. (i) Thibaudeau, C.; Plavec, J.; Garg, N.; Papchikhin, A.; Chattopadhyaya, J. J. Am. Chem. Soc. 1994, 116, 4038.
10. (j) Plavec, J.; Thibaudeau, C.; Chattopadhyaya, J. J. Am. Chem. Soc. 1994, 116, 6558.
11. (k) Thibaudeau, C.; Plavec, J.; Chattopadhyaya, J. J. Am. Chem. Soc. 1994, 116, 8033.
12. (l) J. Plavec Ph.D. Thesis, Department of Bioorganic Chemistry, Uppsala University, Sweden, 1995.
13. (m) Plavec, J.; Thibaudeau, C; Chattopadhyaya, J. Tetrahedron 1995, 57, 11775.
14. (n) Thibaudeau, C.; Plavec, J. and Chattopadhyaya, J. J. Org. Chem. 1996, 61, 266.
15. (o) Chattopadhyaya, J. Nucl. Acids Symposium Series 1996, 35, 111.
16. (p) Plavec, J.; Thibaudeau, C. and Chattopadhyaya, J. Pure and Applied Chemistry, 1996, 68, 2137.
17. (q) Thibaudeau, C. and Chattopadhyaya, J. Nucleosides & Nucleotides 1997, in press.
18. (r) Thibaudeau, C. and Chattopadhyaya, J. J. Org. Chem., 1996, submitted.
19. (a) Cortese, R.; Kammen, H. O.; Spengler, S. J. and Ames, B. N. J. Biol. Chem. 1914, 249, 1103.
20. (b) Samuelsson, T.; Boren, T.; Johansen, T. I. and Lustig, F. J. Biol. Chem. 1988, 263, 13692.
21. (a) Suhadolnik, R. J. Nucleoside Antibiotics, Wiley-Interscience, New York 1970; Nucleosides as Biochemical Probes, Wiley-Interscience, New York 1979; Townsened L. B. in Handbook of Biochemistry and Molecular Biology, 3rd ed., (Fasman G. D. ed.), Vol. 1, p 271, CRC Press, Columbus, Ohio 1975
22. (a) Suhadolnik, R. J. Nucleoside Antibiotics, Wiley-Interscience, New York 1970; Nucleosides as Biochemical Probes, Wiley-Interscience, New York 1979; Townsened L. B. in Handbook of Biochemistry and Molecular Biology, 3rd ed., (Fasman G. D. ed.), Vol. 1, p 271, CRC Press, Columbus, Ohio 1975
23. (a) Suhadolnik, R. J. Nucleoside Antibiotics, Wiley-Interscience, New York 1970; Nucleosides as Biochemical Probes, Wiley-Interscience, New York 1979; Townsened L. B. in Handbook of Biochemistry and Molecular Biology, 3rd ed., (Fasman G. D. ed.), Vol. 1, p 271, CRC Press, Columbus, Ohio 1975
24. (b) Hanessian, S. and Pernet, A. G. Adv. Carbohydr. Chem. Biochem. 1976, 33, 111.
25. (c) Daves, G. D. and Cheng, C. C. Prog. Med. Chem. 1976, 13, 303.
26. (d) Buchanan J. G. Forsch. Chem. Org. Naturst. 1983, 44 243.
27. (e) Hacksell, U. and Daves, G. D. Prog. Med. Chem. 1985, 22, 1.
28. (f) There are other types of C-glycosyl natural products in which the aglycons are not nitrogen heterocycles. Some of these C-glycosyl compounds have shown anticancer activity. Daves G. D. Acc. Chem. Res. 1990, 23, 201.
29. (a) Tvaroska, I.; Bleha, T. Adv. Carbohydr.Chem. 1989, 47, 45.
30. (b) Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019.
31. (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.
32. (d) Box, V. G. S. Heterocycles 1990, 31, 1157.
33. (e) Olson, W.K.; Sussman, J.L. J. Am. Chem. Soc. 1982, 104, 270.
34. (f) Olson, W.K. J. Am. Chem. Soc. 1982, 104, 278.
35. (g) Phillips, L.; Wray, V. J. Chem. Soc., Chem. Commun. 1973, 90.
36. (h) Brunck, T.K.; Weinhold, F. J. Am. Chem. Soc. 1979, 101, 1700.
37. (i) Murcko, M.A.; DiPaola, R.A. J. Am. Chem. Soc. 1992, 114, 10010.
38. (j) Wiberg, K.B.; Murcko, M.A.; Laidig, K.E.; MacDougall, P.J. J. Phys. Chem. 1990, 94, 6956.
39. Edward, J.T. Chem. Ind. (London) 1955, 1102.
40. (a) Lücken, E. A. C.J. Chem. Soc. 1959, 2954.
41. (b) Romers, C.; Altona, C; Buys, H. R.; Havinga, E. Top. Stereochem. 1969, 4, 39.
42. Saenger, W. Principles of Nucleic Acid Structure, Springer Verlag, Berlin, 1988 .
43. Perrin, C. L.; Armstrong, K. B.; Fabian, M. A. J. Am. Chem. Soc. 1994, 116, 715.
44. Salzner, U. J. Org. Chem. 1995, 60, 986.
45. Cosse-Barbi, A.; Watson, D. G.; Dubois, J.E. Tetrahedron Lett. 1989, 30, 163.
46. "Dictionary of Organic Compounds", volume 3, fifth edition, Chapman and Hall, New York, and references therein.
47. Ward, D. C., Reich, E. and Stryer, L. J. Biol. Chem. 1969, 244, 1228.
48. Watanabe, K. A. Chem. Nucleosides Nucleotides 1994, 3, 421. Ed. Townsed, L.B. (Plenum; New York).
49. (a) De Leeuw, F. A. A. M. and Altona, C. J. Comp. Chem. 1983, 4, 428 and PSEUROT, QCPE program No 463.
50. (b) Diez, E.; Fabian, J. S.; Guilleme, J.; Altona, C. and Donders, L.A. Mol. Phys. 1989, 68, 49.
51. (c) Donders, L. A.; de Leeuw, F. A. A. M. and Altona, C. Magn. Reson. Chem. 1989, 27, 556.
52. (d) Altona, C.; Ippel, J.H.; Hoekzema, A. J. A. W.; Erkelens, C.; Groesbeek, G.; Donders, L.A. Magn. Res. Chem. 1989, 27, 564.
53. (e) Van Wijk, J., unpublished result.
54. Wyman, J. and Gill, S. J. Binding and Linkage. Functional Chemistry of Biological Macromolecules; University Science Books: Mill Valley, CA, 1990, 330.
55. (a) The differences between C4′-O4′ and O4′-C1′ bond distances in X-ray crystal structures of most β-D-ribofuranosyl-C-nucleosides are smaller (≡0.01 Å) than in N-counterparts (≡0.03 Å) and therefore we were uncertain of the presence (ref. 1h) of the anomeric effect in β-D-ribofuranosyl-C-nucleosides. For the X-ray crystal structures of pyrimidine β-D-ribofuranosyl-C-nucleoside 4-thio-ψ-uridine, see Barnes, C.L.; Hawkinson, S.W.; Wigles, P.W. Acta Crystallogr., Sect. B 1980, 36, 2299; for isocytidine hydrochloride, see Birnbaum, G.I.; Watanabe, K.A.; Fox, J.J. Can. J. Chem. 1980, 58, 1633; for 2′-chloro-2′-deoxy-l,3-dimethyl-ψ-uridine, see Pankiewicz, K.W.; Watanabe, K.A.; Takayanagi, H.; Itoh, T.; Ogura, H. J. Heterocycl. Chem. 1985, 22, 1703. The X-ray crystal structures of some purine β-D-ribofuranosyl-C-nucleosides have been also elucidated by Koyama, G.; Nakamura, H.; Umezawa, H.; Iitaka, Y. Acta Crystallogr., Sect. B 1976, 32, 813 [for formycin B (2)], Abola, J.E.; Sims, M.J.; Abraham, D.J.; Lewis, A.F.; Townsend, L.B. J. Med. Chem. 1974, 17, 62 (for 2-methyl-formycin A), Prusiner, P.; Brennan, T.; Sundaralingam, M. Biochemistry 1973, 12, 1196 (for formycin A monohydrate).
56. (a) The differences between C4′-O4′ and O4′-C1′ bond distances in X-ray crystal structures of most β-D-ribofuranosyl-C-nucleosides are smaller (≡0.01 Å) than in N-counterparts (≡0.03 Å) and therefore we were uncertain of the presence (ref. 1h) of the anomeric effect in β-D-ribofuranosyl-C-nucleosides. For the X-ray crystal structures of pyrimidine β-D-ribofuranosyl-C-nucleoside 4-thio-ψ-uridine, see Barnes, C.L.; Hawkinson, S.W.; Wigles, P.W. Acta Crystallogr., Sect. B 1980, 36, 2299; for isocytidine hydrochloride, see Birnbaum, G.I.; Watanabe, K.A.; Fox, J.J. Can. J. Chem. 1980, 58, 1633; for 2′-chloro-2′-deoxy-l,3-dimethyl-ψ-uridine, see Pankiewicz, K.W.; Watanabe, K.A.; Takayanagi, H.; Itoh, T.; Ogura, H. J. Heterocycl. Chem. 1985, 22, 1703. The X-ray crystal structures of some purine β-D-ribofuranosyl-C-nucleosides have been also elucidated by Koyama, G.; Nakamura, H.; Umezawa, H.; Iitaka, Y. Acta Crystallogr., Sect. B 1976, 32, 813 [for formycin B (2)], Abola, J.E.; Sims, M.J.; Abraham, D.J.; Lewis, A.F.; Townsend, L.B. J. Med. Chem. 1974, 17, 62 (for 2-methyl-formycin A), Prusiner, P.; Brennan, T.; Sundaralingam, M. Biochemistry 1973, 12, 1196 (for formycin A monohydrate).
57. (a) The differences between C4′-O4′ and O4′-C1′ bond distances in X-ray crystal structures of most β-D-ribofuranosyl-C-nucleosides are smaller (≡0.01 Å) than in N-counterparts (≡0.03 Å) and therefore we were uncertain of the presence (ref. 1h) of the anomeric effect in β-D-ribofuranosyl-C-nucleosides. For the X-ray crystal structures of pyrimidine β-D-ribofuranosyl-C-nucleoside 4-thio-ψ-uridine, see Barnes, C.L.; Hawkinson, S.W.; Wigles, P.W. Acta Crystallogr., Sect. B 1980, 36, 2299; for isocytidine hydrochloride, see Birnbaum, G.I.; Watanabe, K.A.; Fox, J.J. Can. J. Chem. 1980, 58, 1633; for 2′-chloro-2′-deoxy-l,3-dimethyl-ψ-uridine, see Pankiewicz, K.W.; Watanabe, K.A.; Takayanagi, H.; Itoh, T.; Ogura, H. J. Heterocycl. Chem. 1985, 22, 1703. The X-ray crystal structures of some purine β-D-ribofuranosyl-C-nucleosides have been also elucidated by Koyama, G.; Nakamura, H.; Umezawa, H.; Iitaka, Y. Acta Crystallogr., Sect. B 1976, 32, 813 [for formycin B (2)], Abola, J.E.; Sims, M.J.; Abraham, D.J.; Lewis, A.F.; Townsend, L.B. J. Med. Chem. 1974, 17, 62 (for 2-methyl-formycin A), Prusiner, P.; Brennan, T.; Sundaralingam, M. Biochemistry 1973, 12, 1196 (for formycin A monohydrate).
58. (a) The differences between C4′-O4′ and O4′-C1′ bond distances in X-ray crystal structures of most β-D-ribofuranosyl-C-nucleosides are smaller (≡0.01 Å) than in N-counterparts (≡0.03 Å) and therefore we were uncertain of the presence (ref. 1h) of the anomeric effect in β-D-ribofuranosyl-C-nucleosides. For the X-ray crystal structures of pyrimidine β-D-ribofuranosyl-C-nucleoside 4-thio-ψ-uridine, see Barnes, C.L.; Hawkinson, S.W.; Wigles, P.W. Acta Crystallogr., Sect. B 1980, 36, 2299; for isocytidine hydrochloride, see Birnbaum, G.I.; Watanabe, K.A.; Fox, J.J. Can. J. Chem. 1980, 58, 1633; for 2′-chloro-2′-deoxy-l,3-dimethyl-ψ-uridine, see Pankiewicz, K.W.; Watanabe, K.A.; Takayanagi, H.; Itoh, T.; Ogura, H. J. Heterocycl. Chem. 1985, 22, 1703. The X-ray crystal structures of some purine β-D-ribofuranosyl-C-nucleosides have been also elucidated by Koyama, G.; Nakamura, H.; Umezawa, H.; Iitaka, Y. Acta Crystallogr., Sect. B 1976, 32, 813 [for formycin B (2)], Abola, J.E.; Sims, M.J.; Abraham, D.J.; Lewis, A.F.; Townsend, L.B. J. Med. Chem. 1974, 17, 62 (for 2-methyl-formycin A), Prusiner, P.; Brennan, T.; Sundaralingam, M. Biochemistry 1973, 12, 1196 (for formycin A monohydrate).
59. (a) The differences between C4′-O4′ and O4′-C1′ bond distances in X-ray crystal structures of most β-D-ribofuranosyl-C-nucleosides are smaller (≡0.01 Å) than in N-counterparts (≡0.03 Å) and therefore we were uncertain of the presence (ref. 1h) of the anomeric effect in β-D-ribofuranosyl-C-nucleosides. For the X-ray crystal structures of pyrimidine β-D-ribofuranosyl-C-nucleoside 4-thio-ψ-uridine, see Barnes, C.L.; Hawkinson, S.W.; Wigles, P.W. Acta Crystallogr., Sect. B 1980, 36, 2299; for isocytidine hydrochloride, see Birnbaum, G.I.; Watanabe, K.A.; Fox, J.J. Can. J. Chem. 1980, 58, 1633; for 2′-chloro-2′-deoxy-l,3-dimethyl-ψ-uridine, see Pankiewicz, K.W.; Watanabe, K.A.; Takayanagi, H.; Itoh, T.; Ogura, H. J. Heterocycl. Chem. 1985, 22, 1703. The X-ray crystal structures of some purine β-D-ribofuranosyl-C-nucleosides have been also elucidated by Koyama, G.; Nakamura, H.; Umezawa, H.; Iitaka, Y. Acta Crystallogr., Sect. B 1976, 32, 813 [for formycin B (2)], Abola, J.E.; Sims, M.J.; Abraham, D.J.; Lewis, A.F.; Townsend, L.B. J. Med. Chem. 1974, 17, 62 (for 2-methyl-formycin A), Prusiner, P.; Brennan, T.; Sundaralingam, M. Biochemistry 1973, 12, 1196 (for formycin A monohydrate).
60. (a) The differences between C4′-O4′ and O4′-C1′ bond distances in X-ray crystal structures of most β-D-ribofuranosyl-C-nucleosides are smaller (≡0.01 Å) than in N-counterparts (≡0.03 Å) and therefore we were uncertain of the presence (ref. 1h) of the anomeric effect in β-D-ribofuranosyl-C-nucleosides. For the X-ray crystal structures of pyrimidine β-D-ribofuranosyl-C-nucleoside 4-thio-ψ-uridine, see Barnes, C.L.; Hawkinson, S.W.; Wigles, P.W. Acta Crystallogr., Sect. B 1980, 36, 2299; for isocytidine hydrochloride, see Birnbaum, G.I.; Watanabe, K.A.; Fox, J.J. Can. J. Chem. 1980, 58, 1633; for 2′-chloro-2′-deoxy-l,3-dimethyl-ψ-uridine, see Pankiewicz, K.W.; Watanabe, K.A.; Takayanagi, H.; Itoh, T.; Ogura, H. J. Heterocycl. Chem. 1985, 22, 1703. The X-ray crystal structures of some purine β-D-ribofuranosyl-C-nucleosides have been also elucidated by Koyama, G.; Nakamura, H.; Umezawa, H.; Iitaka, Y. Acta Crystallogr., Sect. B 1976, 32, 813 [for formycin B (2)], Abola, J.E.; Sims, M.J.; Abraham, D.J.; Lewis, A.F.; Townsend, L.B. J. Med. Chem. 1974, 17, 62 (for 2-methyl-formycin A), Prusiner, P.; Brennan, T.; Sundaralingam, M. Biochemistry 1973, 12, 1196 (for formycin A monohydrate).
61. DAISY, Spin Simulation Program, provided by Bruker, was used with 7 spins systems.
62. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8205; ibid 1973, 95, 2333.
63. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8205; ibid 1973, 95, 2333.
64. m(S)).
65. proFit version 4.2, Quantum Soft, Postfach 6613, CH - 8023 Zürich, Switzerland 1990-94