Use of 1,2,4-dithiazolidine-3,5-dione (DtsNH) and 3-ethoxy-1,2,4-dithiazoline-5-one (EDITH) for synthesis of phosphorothioate-containing oligodeoxyribonucleotides

Nucleic Acids Research

Volumn 24, Issue 9, 1996, Pages 1602-1607

  Xu, Qinghong ^a   Musier Forsyth, Karin ^a   Hammer, Robert P ^b   Barany, George ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; OLIGODEOXYNUCLEOTIDE PHOSPHOROTHIOATE; SULFUR; THIAZOLIDINE DERIVATIVE;

ARTICLE; DNA SYNTHESIS; METHODOLOGY; PRIORITY JOURNAL;

BASE SEQUENCE; INDICATORS AND REAGENTS; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; OLIGODEOXYRIBONUCLEOTIDES; THIAZOLES; THIAZOLIDINEDIONES; THIONUCLEOTIDES;

EID: 0029993626     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/24.9.1602     Document Type: Article

References (41)

1. Eckstein, F. and Gish, G. (1989) TIBS, 14, 97-100
2. Zon, G. and Stec, W.J. (1991) In Eckstein, F. (ed.), Oligonucleotides and Analogues: A Practical Approach. IRL Press, Oxford, pp. 87-108.
3. Iversen, P. (1991) Anti-Cancer Drug Des., 6, 539-568.
4. Uhlmann, E. and Peyman, A. (1990) Chem. Rev., 90, 544-583.
5. Gao, W.-Y., Han, F.-S., Storm, C., Egan, W and Cheng, Y.-C. (1992) Mol. Pharmacol., 41, 223-229.
6. Wagner, R.W. (1994) Nature, 372, 333-335.
7. Bongartz, J.-P., Aubertin, A.-M., Milhaud, P.G. and Lebleu, B. (1994) Nucleic Acids Res., 22, 4681-4688.
8. Fidanza, J.A., Ozaki, H. and McLaughlin, L.W. (1992) J. Am. Chem. Soc., 114, 5509-5517.
9. Musier-Forsyth, K. and Schimmel, P. (1994) Biochemistry, 33, 773-779.
10. Koziolkiewicz, M. and Stec, W.J. (1992) Biochemistry, 31, 9460-9466.
11. Milligan, J.F. and Uhlenbeck, O.C. (1989) Biochemisty, 28, 2849-2855.
12. Moore, M.J. and Sharp, P.A. (1993) Nature. 365, 364-368.
13. Garegg, P.J., Regberg, T., Stawinski, J. and Strömberg, R. (1985) Chemica Scripta, 25, 280-282.
14. Froehler, B C. (1986) Tetrahedron Lett., 27, 5575-5578.
15. Agrawal, S. and Tang, J.-Y. (1990) Tetrahedron Lett., 31, 7541-7544.
16. Stec, W.J., Zon, G., Egan, W. and Stec, B. (1984) J. Am. Chem. Soc., 106, 6077-6079.
17. Connolly, B.A., Potter, B V.L., Eckstein, F., Pingoud, A. and Grotjahn, L. (1984) Biochemistry, 23, 3443-3453.
18. Iyer, R.P., Phillips, L.R., Egan, W., Regan, J.B. and Beaucage, S.L. (1990) J. Org. Chem., 55, 4693-4699.
19. Vu, H. and Hirschbein, B.L (1991) Tetrahedron Lett., 32, 3005-3008.
20. Roelen, H.C.P.F., Kamer, P.C.J., van den Elst, H., van der Marel, G.A. and van Boom, J.H. (1991) Recl. Trav. Chim. Pays-Bas., 110, 325-331.
21. Rao, M.V., Reese, C.B. and Zhengyun, Z. (1992) Tetrahedron Lett., 33, 4839-4842.
22. Stec, W.J., Uznanski, B., Wilk, A., Hirschbein, B.L., Fearon, K.L. and Bergot, B.J. (1993) Tetrahedron Lett., 34, 5317-5320.
23. Rao, M.V. and Macfarlane, K. (1994) Tetrahedron Lett., 35, 6741-6744.
24. Efimov, V. A., Kalinkina, A. L., Chakhmakhcheva, O. G., Hill, T. S. and Jayaraman, K. (1995) Nucleic Acids Res., 23, 4029-4033.
25. Zumach, G. and Kühle, E. (1970) Angew Chem. Int. Ed. Engl., 9, 54-63.
26. Dahms, G., Haas, A. and Klug, W. (1971) Chem. Ber., 104, 2732-2742.
27. Barany, G. Ph.D. thesis (1977) The Rockefeller University, Dissertation Abstr., 38, 5893-B.
28. Chen, L., Thompson, T.R., Hammer, R.P. and Barany, G. (1996) submitted
29. Wyrzykiewicz, T. K. and Cole, D. L. (1995) Bioorg. Chem., 23, 33-41.
30. Ausserer, W. A. and Biros, M. L. (1995) BioTechniques, 19, 136-139.
31. Sproat, B., Colonna, F., Mullah, B., Tsou, D., Andrus, A., Hampel, A. and Vinayak, R. (1995) Nucleoside Nucleotides, 14, 255-273.
32. Bergot, B. J. (Mar. 7, 1995) U. S. Patent, 5, 395,928.
33. Little, D. P., Chorush, R. A., Speir, J. P., Senko, M. W., Kelleher, N. L. and McLafferty, F. W. (1994) J. Am. Chem. Soc., 116, 4893-4897.
34. Potier, N., Van Dorsselaer, A., Cordier, Y., Roch, O. and Bischoff, R. (1994) Nucleic Acids Res., 22, 3895-3903.
35. Barany, G. and Merrifield, R.B. (1977) J. Am. Chem. Soc., 99, 7363-7365.
36. Barany, G. and Merrifield, R.B. (1979) Anal. Biochem., 95, 160-170.
37. Barany, G. and Merrifield, R.B. (1980) J. Am Chem. Soc., 102, 3084-3095.
38. Barany, G. (1982) Crystal Structure Commun., 11, 913-928.
39. Albericio, F. and Barany, G. (1987) Int. J. Peptide Protein Res., 30, 177-205.
40. Barany, G., Albericio, F., Chang, J.L., Ferrer, M., Hammer, R.P., Kneib-Cordomer, N., Ottinger, E.A. and Solé, N.A. (1992) ORGN 184. American Chemical Society, 203rd National Meeting, San Francisco, California, April 5-10, 1992.
41. Hammer, R.P. and Barany, G. (1987) American Chemical Society, 21st Great Lakes Regional Meeting, Chicago, Illinois, June 10-12, 1987.