Comprehensive structural studies of 2′,3′-difluorinated nucleosides: Comparison of theory, solution, and solid state

Journal of the American Chemical Society

Volumn 130, Issue 28, 2008, Pages 9048-9057

  Barchi Jr , Joseph J ^a   Karki, Rajeshri G ^a,b   Nicklaus, Marc C ^a   Siddiqui, Maqbool A ^a   George, Clifford ^a,c   Mikhailopulo, Igor A ^a,d   Marquez, Victor E ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

^c NAVAL RESEARCH LABORATORY   (United States)

^d INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

[No Author keywords available]

Indexed keywords

ARSENIC COMPOUNDS; ATOMIC PHYSICS; ATOMIC SPECTROSCOPY; CRYSTALLOGRAPHY; FLUORINE; MINERALOGY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDES; ORGANIC POLYMERS; SOLID SOLUTIONS; X RAY CRYSTALLOGRAPHY;

AB INITIO CALCULATIONS; FLUORINE ATOMS; FURANOSE RING; NMR SPECTROS COPY; SOLID STATES; STRUCTURAL STUDIES; X RAY CRYSTALLOGRAPHY;

ATOMS;

FLUORINE; NUCLEOSIDE;

AB INITIO CALCULATION; ARTICLE; CONFORMATION; DEFLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; THEORETICAL STUDY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; DEOXYURIDINE; FLUORINE; FOURIER ANALYSIS; HYDROCARBONS, FLUORINATED; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRIMIDINE NUCLEOSIDES; URACIL; URIDINE;

EID: 47349092659     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800964g     Document Type: Article

References (44)

1. Ismail, F. M. D. J. Fluorine Chem. 2002, 118, 27-33.
2. Kirk, K. L.; Filler, R. Biomed. Front. Fluorine Chem. 1996, 639, 1-24.
3. Park, B. K.; Kitteringham, N. R.; O'Neill, P. M. Annu. Rev. Pharmacol. Toxicol. 2001, 41, 443-470.
4. Meng, W. D.; Qing, F. L. Curr. Top. Med. Chem. 2006, 6, 1499-1528.
5. Pankiewicz, K. W. Carbohydr. Res. 2000, 327, 87-105.
6. Marquez, V. E.; Tseng, C. K. H.; Mitsuya, H.; Aoki, S.; Kelley, J. A.; Ford, H.; Roth, J. S.; Broder, S.; Johns, D. G.; Driscoll, J. S. J. Med Chem. 1990, 33, 978-985.
7. Roth, J. S.; McCully, C. M.; Balis, F. M.; Poplack, D. G.; Kelley, J. A. Drug Metab. Dispos. 1999, 27, 1128-1132.
8. "Lodenosine Trial Halted", Aids Patient Care and Stds. 2000, 14, 61.
9. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333-2344.
10. Vanroey, P.; Salerno, J. M.; Chu, C. K.; Schinazi, R. F. Proc. Natl. Acad. Sci. U. S. A. 1989, 86, 3929-3933.
11. Mirmehrabi, M.; Rohani, S.; Jennings, M. C. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2005, 61, O695-O698.
12. Jagannadh, B.; Reddy, D. V.; Kunwar, A. C. Biochem. Biophys. Res. Commun. 1991, 179, 386-391.
13. Abraham, R. J.; Chambers, E. J.; Thomas, W. A. J. Chem. Soc., Perkins Trans. 2 1994, 949-955.
14. Tavasli, M.; O'Hagan, D.; Pearson, C.; Petty, M. C. Chem. Commun. 2002, 1226-1227.
15. Thibaudeau, C.; Acharya, P.; Chattopadhyaya, J. Stereoelectronic Effects in Nucleosides & Nucleotides and their Structural Implications; 2nd ed.; Uppsala University Press: Uppsala, Sweden, 2005.
16. Mikhailopulo, I. A.; Pricota, T. I.; Sivets, G. G.; Altona, C. J. Org. Chem. 2003, 68, 5897-5908.
17. Sivets, G. G.; Kalinichenko, E. N.; Mikhailopulo, I. A. Lett. Org. Chem. 2006, 3, 402-408.
18. Sivets, G. G.; Kalinichenko, E. N.; Mikhailopulo, I. A. Helv. Chim. Acta 2007, 90, 1818-1836.
19. Brunck, T. K.; Weinhold, F. J. Am. Chem. Soc. 1979, 101, 1700-1709.
20. Marquez, V. E.; Lim, B. B.; Barchi, J. J., Jr.; Nicklaus, M. C. Conformational Studies and Anti-HIV Activity of Mono- and Difluorodideoxy Nucleosides; Plenum Press, New York: 1993; pp 265-284.
21. Bergstrom, D. E.; Swartling, D. J.; Wisor, A.; Hoffmann, M. R. Nucleosides Nucleotides 1991, 10, 693-697.
22. Martin, J. A.; Bushneil, D. J.; Duncan, I. B.; Dunsdon, S. J.; Hall, M. J.; Machin, P. J.; Merrett, J. H.; Parkes, K. E. B.; Roberts, N. A.; Thomas, G. J.; Galpin, S. A.; Kinchington, D. J. Med. Chem. 1990, 33, 2137-2145.
23. SMART and SAINT, Bruker AXS: Madison, WI, 1999.
24. Sheldrick, G. M. SHELXS97 and SHELXL97; University of Göttingen, Göttingen, Germany, 1997.
25. Halgren, T. A. J. Comput. Chem. 1996, 17, 490-519.
26. Qiu, D.; Shenkin, P. S.; Hollinger, F. P.; Still, W. C. J. Phys. Chem. A 1997, 101, 3005-3014.
27. Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379-4386.
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gaussian 98; Gaussian, Inc.: Pittsburgh, 1998.
29. Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.
30. Kupce, E.; Freeman, R. Chem. Phys. Lett. 1996, 250, 523-527.
31. Kupce, E.; Boyd, J.; Campbell, I. D. J. Magn. Res., Ser. B 1995, 106, 300-303.
32. Stott, K.; Stonehouse, J.; Keeler, J.; Hwang, T. L.; Shaka, A. J. J. Am. Chem. Soc 1995, 117, 4199-4200.
33. Thibaudeau, C.; Plavec, J.; Chattopadhyaya, J. J. Org. Chem. 1998, 63, 4967-4984.
34. Plavec, J.; Tong, W. M.; Chattopadhyaya, J. J. Am. Chem. Soc. 1993, 115, 9734-9746.
35. Koole, L. H.; Plavec, J.; Liu, H. Y.; 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, 9936-9943.
36. Thibaudeau, C.; Kumar, A.; Bekiroglu, S.; Matsuda, A.; MarquezV. E.; Chattopadhyaya, J. J. Org. Chem. 1998, 63, 5447-5462.
37. Watts, J. K.; Sadalapure, K.; Choubdar, N.; Pinto, B. M.; Damha, M. J. J. Org. Chem. 2006, 73, 921-925.
38. Seela, F.; Chittepu, P.; He, J.; Eickmeier, H. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2004, 60, O884-O886.
39. Barchi, J. J.; Jeong, L. S.; Siddiqui, M. A.; Marquez, V. E. J. Biochem. Biophys. Methods 1997, 34, 11-29.
40. Barchi, J. J.; Marquez, V. E.; Driscoll, J. S.; Ford, H.; Mitsuya, H.; Shirasaka, T.; Aoki, S.; Kelley, J. A. J. Med. Chem. 1991, 34, 1647-1655.
41. Wasylishen, R. E.; Barfield, M. J. Am. Chem. Soc. 1975, 97, 4545-4552.
42. Ford, H.; Dai, F.; Mu, L.; Siddiqui, M. A.; Nicklaus, M. C.; Anderson, L.; Marquez, V. E.; Barchi, J. J. Biochemistry 2000, 39, 2581-2592.
43. Mikhailopulo, I. A.; Sokolov, Y. A.; He, J. L.; Chittepu, P.; Rosemeyer, H.; Seela, F. Nucleosides Nucleotides Nucl. Acids 2005, 24, 701-705.
44. Amos, R. D.; Handy, N. C.; Jones, P. G.; Kirby, A. J.; Parker, J. K.; Percy, J. M.; Su, M. D. J. Chem. Soc., Perkins Trans. 2 1992, 549-558.