Synthesis of oligonucleotides containing thiazole and thiazole N-oxide nucleobases

Organic Letters

Volumn 4, Issue 6, 2002, Pages 877-880

  Miller, Tod J ^a   Farquar, Hannah D ^a   Sheybani, Arsham ^a   Tallini, Camille E ^a   Saurage, Andrea S ^a   Fronczek, Frank R ^a   Hammer, Robert P ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE; OLIGONUCLEOTIDE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; NUCLEOSIDES; OLIGONUCLEOTIDES; THIAZOLES;

EID: 0037149667     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017003g     Document Type: Article

References (21)

1. Daves, G. D., Jr.; Cheng, C. C. Prog. Med. Chem. 1976, 13, 303-349.
2. Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1-65.
3. Loakes, D. Nucleic Acids Res. 2001, 29, 2437-2447.
4. Steitz, T. A. J. Biol. Chem. 1999, 274, 17395-17398.
5. Kiefer, J. R.; Mao, C.; Braman, J. C.; Beese, L. S. Nature 1998, 391, 304-307.
6. Eom, S. H.; Wang, J. M.; Steitz, T. A. Nature 1996, 382, 278-281.
7. Quo, M. J.; Hildbrand, S.; Leumann, C. J.; McLaughlin, L. W.; Waring, M. J. Nucleic Acids Res. 1998, 26, 1863-1869.
8. (a) Gutierrez, A. J.; Terhorst, T. J.; Matteucci, M. D.; Froehler, B. C. J. Am. Chem. Soc. 1994, 116, 5540-5544.
9. (b) Hammer, R. P.; Cameron, M. A.; Sapp, A. L. Synthesis and Thermodynamic Properties of Nucleic Acids containing Non-Hydrogen-Bonding Nucleoside Analogues, T225; 35th National Organic Symposium, Trinity University, San Antonio, Texas, June 22-26, 1997.
10. Begtrup, M.; Hansen, L. B. L. Acta Chem. Scand. 1992, 46, 372-383.
11. Srivastava, P. C.; Pickering, M. V.; Allen, L. B.; Streeter, D. G.; Campbell, M. T.; Witkowski, J. T.; Sidwell, R. W.; Robins, R. K. J. Med. Chem. 1977, 20, 256-262.
12. Dalley, N. K.; Pétrie, C. R., III; Revankar, G. R.; Robins, R. K. Nucleosides Nucleotides 1985, 4, 651-659.
13. Ramasamy, K. S.; Lau, J. Y. N. Nucleosides Nucleotides Nucleic Acids 2001, 20, 1329-1331.
14. Vernin, G. In Thiazole and Its Derivatives; Metzaer, J. V., Ed.; John Wiley & Sons: New York, 1979; Vol. 34, pp 165-335.
15. Wigerinck, P.; Snoeck, R.; Claes, P.; Declercq, E.; Herdewijn, P. J. Med. Chem. 1991, 34, 1767-1772.
16. Baldwin, J. J.; Christy, M. E.; Denny, G. H.; Habecker, C. N.; Freedman, M. B.; Lyle, P. A.; Ponticello, G. S.; Varga, S. L.; Gross, D. M.; Sweet, C. S. J. Med. Chem. 1986, 29, 1065-1080.
17. Caron, S.; Do, N. M.; Sieser, J. E. Tetrahedron Lett. 2000, 41, 2299-2302.
18. Goldstein, B. M.; Takusagawa, F.; Berman, H. M.; Srivastava, P. C.; Robins, R. K. J. Am. Chem. Soc. 1983, 105, 7416-7422.
19. Ochiai, E. In Aromatic Amine Oxides; Elsevier Publishing Company: New York, 1967; pp 190-196.
20. Albini, A.; Pietra, S. In Heterocyclic N-oxides; CRC Press: Boca Raton, FL, 1991; pp 120-123.
21. Thiazole N-oxide phosphoramidite 11 is stable for 1 year when stored at -20°C.