Triarylmethyl substituted 4,5-dicyanoimidazoles as activators for Rp- diastereoselective synthesis of TpN dinucleoside methylphosphonates

Nucleosides and Nucleotides

Volumn 18, Issue 6-7, 1999, Pages 1169-1174

  Schell, Peter ^a   Laux, Wolfgang H G ^a   Engels, Joachim W ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4,5 DICYANOIMIDAZOLE DERIVATIVE; DICHLOROMETHANE; IMIDAZOLE DERIVATIVE; METHYLPHOSPHONIC ACID; NICOTINAMIDE; OLIGODEOXYNUCLEOTIDE; PYRROLE; UNCLASSIFIED DRUG;

CATALYSIS; CHEMICAL REACTION; CHIMERA; CHIRALITY; CONFERENCE PAPER; DIASTEREOISOMER; PROTEIN DNA BINDING; PROTEIN RNA BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032781544     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319908044654     Document Type: Conference Paper

References (30)

1. a) Miller, P. S. Bio/Technology, 1991, 9, 358-362;
2. b) Miller, P. S. Progress in Nucleic Acid Research and Molecular Biology, 1996, 52, 261-291.
3. Uhlmann, E.; Peyman, A. Chem. Rev., 1990, 90, 543-584.
4. Giles, R. V.; Spiller, D. G.; Grzybowski, J.; Clark, R. E.; Nicklin, P. and Tidd, D. T. Nucleic Acids Res., 1998, 26, 1567-1575.
5. Agrawal, S.; Jiang, Z.; Zhao, Q.; Shaw, D.; Sun, D.; Saxinger, C. Nucleosides & Nucleotides, 1997, 16(7-9), 927-936.
6. On the problem of P-substituted oligonucleotides: Lebedev, A. V.; Wickstrom, E. Perspectives in Drug Discovery and Design, 1996, 4, 17-40, cit. Lit..
7. a) Lesnikowski, Z. J.; Jaworska, M.; Stec, W. J. Nucleic Acids Res., 1990, 18, 2109-2115;
8. b) Vyazovkina, E. V.; Savchenko, E. V.; Lokhov, S. G.; Engels, J. W.; Wickstrom, E.; Lebedev, A. V. ibid., 1994, 22, 2404-2409;
9. c) Reynolds, M. A.; Hogrefe, R. I.; Jaeger, J. A.; Schwartz, D. A.; Riley, T. A.; Marvin, W. B.; Daily, W. J.; Vaghefi, M. M.; Knowles, S. K.; Klem, R. E.; Arnold Jr., L. J. ibid., 1996, 24, 4584-4591.
10. a) Smith, S. A.; McLaughlin, L. W. Biochemistry, 1997, 36, 6046-6058;
11. b) Strauss-Soukup, J. K.; Vaghefi, M. M.; Hogrefe, R. I.; Maher III, L. J. ibid., 1997, 36, 8692-8698;
12. c) Iwai, S.; Maeda, M.; Shimada, Y.; Hori, N.; Murata, T.; Morioka, H.; Ohtsuka, E. ibid., 1994, 33, 5581-5588;
13. d) Pritchard, C. E.; Grasby, J. A.; Hamy, F.; Zacharek, A. M.; Singh, M.; Karn, J.; Gait, M.J. Nucleic Acids Res., 1994, 22, 2592-2600;
14. e) Noble, S. A.; Fisher, E. F.; Caruthers, M. H. ibid., 1984, 12, 3387-3404.
15. a) Lesnikowski, Z. J. Bioorganic Chemistry, 1993, 21, 127-155, cit. Lit.;
16. b) Jaworska-Maslanka, M. M.; Kacperczyk, W.; Korczynski, D.; Lesnikowski, Z. J. Antisense & Nucleic Acid Drug Development, 1997, 7, 23-30;
17. c) Daily, W. J.; Schwartz, D. A.; Riley, T. A.; Arnold Jr., L. J.; Marvin, WO. B.; Scurria, M. A.; Hopkins, S. A.; Atkins, M. B.; Garcia, C. D.; Pirrung, M. C. Nucleosides & Nucleotides, 1997, 16(4), 417-432;
18. d) Stec, W. J.; Wozniak, L. A.; Pyzowski, J.; Niewiarowski, W. Antisense & Nucleic Acid Drug Development, 1997, 7, 381-395.
19. a) LeBec, C.; Wickstrom, E. Tetrahedron Lett., 1994, 35, 9525-9528;
20. b) LeBec, C.; Wickstrom, E. J. Org. Chem., 1996, 61, 510-513.
21. a) Dahl, B. H.; Nielsen, J.; Dahl, O. Nucleic Acids Res., 1987, 15(4), 1729-1743;
22. b) Berner, S.; Mühlegger, K.; Seliger, H. ibid., 1989, 17(3), 853-864.
23. Stec, W.J.; Zon, G. Tetrahedron Lett., 1984, 25(46), 5279-5282.
24. Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn., 1995, 68, 36-56.
25. Schell, P.; Engels, J. W. Tetrahedron Lett., submitted for publication.
26. Zieger, H. E.; Wo, S. J. Org. Chem., 1994, 59, 3838-3840.
27. LeBel, N. A.; Post, M. E.; Whang, J. J. J. Am. Chem. Soc., 1964, 86, 3759-3767.
28. Begland, R. W.; Hartter, D. R.; Jones, F. N.; Sam, D. J.; Sheppard, W. A.; Webster, O. W.; Weigert, F. J. J. Org. Chem., 1974, 39(16), 2341-2350.
29. Moriya, O.; Minamide, H.; Urata, Y. Synthesis, 1984, 1057-1058.
30. Egert, E.; Beck, H.; Bolte, M.; Gemmel, E. "MOMO 2.00 - A Molecular Modeling Program", Frankfurt University, 1997.