The transmission of the electronic character of guanin-9-yl drives the sugar-phosphate backbone torsions in guanosine 3',5'-bisphosphate

Angewandte Chemie - International Edition

Volumn 38, Issue 24, 1999, Pages 3645-3650

  Acharya, Parag ^a   Trifonova, Anna ^a   Thibaudeau, Christophe ^a   Földesi, András ^a   Chattopadhyaya, Jyoti ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Conformation analysis; NMR spectroscopy; Nucleotides; Protonations; RNA

Indexed keywords

GUANINE DERIVATIVE; GUANOSINE 3' DIPHOSPHATE 5' DIPHOSPHATE; PENTOSE PHOSPHATE; RNA; SUGAR PHOSPHATE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; MOLECULAR DYNAMICS; STEREOCHEMISTRY;

EID: 0033576566     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991216)38:24<3645::AID-ANIE3645>3.0.CO;2-O     Document Type: Article

References (42)

1. a) W. Saenger, Principles of Nucleic Acid Structure, Springer, Berlin, 1988;
2. b) R. E. Peter, J. Dandliker, J. K. Barton, Angew. Chem. 1997, 109, 2830-2848; Angew. Chem. Int. Ed. Engl. 1997, 36, 2714-2730;
3. b) R. E. Peter, J. Dandliker, J. K. Barton, Angew. Chem. 1997, 109, 2830-2848; Angew. Chem. Int. Ed. Engl. 1997, 36, 2714-2730;
4. c) E. Meggers, D. Kusch, M. Spichty, U. Wille, B. Giese, Angew. Chem. 1998, 110, 507-510; Angew. Chem. Int. Ed. 1998, 37, 460-465.
5. c) E. Meggers, D. Kusch, M. Spichty, U. Wille, B. Giese, Angew. Chem. 1998, 110, 507-510; Angew. Chem. Int. Ed. 1998, 37, 460-465.
6. a) L. H. Koole, H. M. Buck, A. Nyilas, J. Chattopadhyaya, Can. J. Chem. 1987, 65, 2089;
7. b) J. Plavec, W. Tong, J. Chattopadhyaya, J. Am. Chem. Soc. 1993, 115, 9734;
8. c) J. Plavec, C. Thibaudeau, G. Viswanadham, C. Sund, J. Chattopadhyaya, J. Chem. Soc. Chem. Commun. 1994, 781;
9. d) C. Thibaudeau, J. Plavec, N. Garg, A. Papchikhin, J. Chattopadhyaya, J. Am. Chem. Soc. 1994, 116, 4038;
10. e) J. Plavec, C. Thibaudeau, J. Chattopadhyaya, J. Am. Chem. Soc. 1994, 116, 6558;
11. f) J. Plavec, C. Thibaudeau, G. Viswanadham, C. Sund, A. Sandstrom, J. Chattopadhyaya, Tetrahedron 1995, 51, 11 775, and references therein;
12. g) C. Thibaudeau, J. Plavec, J. Chattopadhyaya, J. Org. Chem. 1996, 61, 266;
13. h) J. Plavec, C. Thibaudeau, J. Chattopadhyaya, Pure Appl. Chem. 1996, 68, 2137;
14. C. Thibaudeau, A. Földesi, J. Chattopadhyaya, Tetrahedron 1997, 53, 14043;
15. j) I. Luyten, C. Thibaudeau, J. Chattopadhyaya, J. Org. Chem. 1997, 62, 8800;
16. k) I. Luyten, C. Thibaudeau, J. Chattopadhyaya, Tetrahedron 1997, 53, 6433;
17. C. Thibaudeau, J. Plavec, J. Chattopadhyaya, J. Org. Chem. 1998, 63, 4967.
18. a) Review: C. Thibaudeau, J. Chattopadhyaya, Stereoelectronic Effects in Nucleosides and Nucleotides and Their Structural Implications, Uppsala University Press, 1999, pp. 27-29 (for the two-state N ⇌ S pseudorotational equilibrium model), 5-23 (for anomeric and gauche effects);
19. b) H. P. M. de Leeuw, C. A. G. Haasnoot, C. Altona, Isr. J. Chem. 1980, 20, 108.
20. a) P. A. Petillo, L. A. Lerner in The Anomeric Effect and Associated Stereoelectronic Effects (Ed.: G. R. J. Thatcher), ACS, Washington DC, 1993, p. 156, and references therein:
21. b) C. L. Perrin, K. B. Armstrong, M. A. Fabian, J. Am. Chem. Soc. 1994, 116, 715.
22. a) P. Dionne, M. St.-Jacques, J. Am. Chem. Soc. 1987, 109, 2616;
23. b) K. B. Wiberg, Acc. Chem. Res. 1996, 29, 229, and references therein.
24. a) C. Altona, M. Sundaralingam, J. Am. Chem. Soc. 1972, 94, 8205;
25. b) C. Altona, M. Sundaralingam, J. Am. Chem. Soc. 1973, 95, 2333.
26. a) F. A. A. M. De Leeuw, C. Altona, J. Comput. Chem. 1983, 4, 428; PSEUROT, QCPE program no. 463, Department of Chemistry, University of Leiden, The Netherlands, 1989;
27. a) F. A. A. M. De Leeuw, C. Altona, J. Comput. Chem. 1983, 4, 428; PSEUROT, QCPE program no. 463, Department of Chemistry, University of Leiden, The Netherlands, 1989;
28. b) C. A. G. Haasnoot, F. A. A. M. de Leeuw, C. Altona, Tetrahedron 1980, 36, 2783.
29. a) E. Diez, J. S. Fabian, J. Guilleme, C. Altona, L. A. Donders, Mol. Phys. 1989, 68, 49;
30. b) L. A. Donders, F. A. A. M. de Leeuw, C. Altona, Magn. Reson. Chem. 1989, 27, 556;
31. c) C Altona, J. H. Ippel, A. J. A. W. Hoekzema, C. Erkelens, G. Groesbeek, L. A. Donders, Magn. Reson. Chem. 1989, 27, 564;
32. d) J. van Wijk, unpublished results.
33. a) M. M. Dhingra, A. Saran, Biopolymers 1982, 21, 859;
34. b) P.P. Lankhorst, C. A. G. Haasnoot, C. Erkelens, C. Altona, J. Biomol. Struct. Dyn. 1984, I. 13870;
35. c) M. J. J. Blommers. D. Nanz, O. Zerbe, J. Biomol. NMR 1994, 4, 595.
36. a) W. H. Press, B. P. Flannery, S.A. Tenkolsky, W. T. Vatterling, Numerical recipes (Fortran version), Cambridge University Press, New York, 1999;
37. b) M. M. W. Mooren, S. S. Wijmenga, G. A. van der Marel, J. H. van Boom, C. W. Hilbers, Nucleic Acids Res. 1994, 22, 2658;
38. c) J. Plavec, J. Chattopadhyaya, Tetrahedron 1995, 36, 1949.
39. See reference [1a], pp. 93-96, and references therein for the anomeric effect across the 3'O-P-O-ester fragment in the sugar-phosphate backbone.
40. 1, ζ , α, and S, ε , ζ, α conformations of 1 to draw the Newman projections are provided in Table S6 in the Supporting Information.
41. a) C. A. G. Haasnoot, F. A. A. M. de Leeuw, H. P. M. de Leeuw, C. Altona. Recl. Trav. Chim. Pays-Bas 1979, 98, 576;
42. b) H. Rosemeyer, G. Tóth, B. Golankiewicz, Z. Kazimierczuk, W. Bourgeois, U. Kretschmer, H. P Muth, F. Seela, J. Org. Chem. 1990, 55, 5784.