Chimera of dimethylene sulfone-, methyl sulfide-, and methyl sulfoxide-linked ribonucleotides and DNA

Journal of Organic Chemistry

Volumn 61, Issue 21, 1996, Pages 7620-7626

  Baeschlin, Daniel K ^a   Hyrup, Birgitte ^a,b   Benner, Steven A ^a   Kichert, Clemens ^a,c  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c TUFTS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEIC ACID; OLIGODEOXYNUCLEOTIDE;

ARTICLE; DRUG SYNTHESIS; HYBRIDIZATION;

EID: 0029855948     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960669h     Document Type: Article

References (35)

1. See, e.g.: (a) Eschenmoser, A. Pure Appl. Chem. 1993, 65, 1179-1188. (b) Hunziker, J.; Roth, H.-J.; Böhringer, M.; Giger, A.; Diederichsen, U.; Göbel, M.; Krishnan, R.; Jaun, B.; Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1993, 76, 259-351. (c) Schneider, K. C.; Benner, S. A. J. Am. Chem. Soc. 1990, 112, 453-455.
2. See, e.g.: (a) Eschenmoser, A. Pure Appl. Chem. 1993, 65, 1179-1188. (b) Hunziker, J.; Roth, H.-J.; Böhringer, M.; Giger, A.; Diederichsen, U.; Göbel, M.; Krishnan, R.; Jaun, B.; Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1993, 76, 259-351. (c) Schneider, K. C.; Benner, S. A. J. Am. Chem. Soc. 1990, 112, 453-455.
3. See, e.g.: (a) Eschenmoser, A. Pure Appl. Chem. 1993, 65, 1179-1188. (b) Hunziker, J.; Roth, H.-J.; Böhringer, M.; Giger, A.; Diederichsen, U.; Göbel, M.; Krishnan, R.; Jaun, B.; Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1993, 76, 259-351. (c) Schneider, K. C.; Benner, S. A. J. Am. Chem. Soc. 1990, 112, 453-455.
4. (a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745-1768.
5. (b) Perigaud, C.; Gosselin, G.; Imbach, J.-L. Nuclesides Nucleotides 1992, 11, 903-945.
6. (a) Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 544-584.
7. (b) Milligan, J. F.; Matteucci, M. D.; Martin, J. C. J. Med. Chem. 1993, 36, 1923-1937.
8. (a) Huang, Z.; Schneider, K. C.; Benner, S. A. J. Org. Chem. 1991, 56, 3869-3882.
9. (b) Schneider, K. C.; Benner, S. A. Tetrahedron Lett. 1990, 31, 335-338.
10. (c) Richert, C.; Roughton, A. L.; Benner, S. A. J. Am. Chem. Soc. 1996, 118, 4518-4531.
11. Roughton, A. L.; Portmann, S.; Benner, S. A.; Egli, M. J. Am. Chem. Soc. 1995, 117, 7249-7250.
12. Hyrup, B.; Richert, C.; Schulte-Herbrüggen, T.; Benner, S. A.; Egli, M. Nucleic Acids Res. 1995, 23, 2427-2433.
13. Szarek, W. A.; Zamojski, A.; Tiwari, K. N.; Ison, E. R. Tetrahedron Lett. 1986, 27, 3827-3830.
14. (a) Vorbrüggen, H.; Bennua, B. Chem. Ber. 1981, 114, 1279-1286.
15. (b) Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234-1255.
16. Baeschlin, D. K.; Daube, M;. Blättler, M. O.; Benner, S. A.; Richert, C. Tetrahedron Lett. 1996, 37, 1591-1592.
17. Kierzek, R.; Kopp, D. W.; Edmonds, M.; Caruthers, M. H. Nucleic Acids Res. 1986, 14, 4751-4764.
18. Pieles, U.; Zürcher, W.; Schär, M.; Moser, H. E. Nucleic Acids Res. 1993, 21, 3191-3196.
19. Habus, I.; Temsamani, J.; Agrawal, S. Bioorg. Med. Chem. Lett. 1994, 4, 1065-1070.
20. Bjergårde, K.; Dahl, O. Nucleic Acids Res. 1991, 19, 5843-5850.
21. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984.
22. Meng, B.; Kawai, S. H.; Wang, D.; Just, G.; Giannaris, P. A.; Damha, M. J. Angew. Chem. 1993, 105, 733-735; Angew. Chem., Int. Ed. Engl. 1993, 32, 729-731.
23. Meng, B.; Kawai, S. H.; Wang, D.; Just, G.; Giannaris, P. A.; Damha, M. J. Angew. Chem. 1993, 105, 733-735; Angew. Chem., Int. Ed. Engl. 1993, 32, 729-731.
24. Vesnaver, G.; Breslauer, K. J. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 3569-3573.
25. Hunziker, J.; Leumann, C. Nucleic Acid Analogues: Synthesis and Properties. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, 1995; pp 333-417.
26. Verheyden, J. P. H.; Moffatt, J. G. J. Org. Chem. 1972, 37, 2289-2299.
27. Kawai, S. H.; Wang, D.; Giannaris, P. A.; Damha, M. J.; Just, G. Nucleic Acids Res. 1993, 21, 1473-1479.
28. Just, G.; Kawai, S. H. In Carbohydrate Modifications in Antisense Research; Saghvi, Y. S., Cook, P. D., Eds.; ACS Symposium Series: Washington, DC, 1994; pp 52-65.
29. See, e.g.: (a) Gait, M. J.; Grasby, J. A.; Karn, J.; Mersmann, K.; Pritchard, C. E. Nucleosides Nucleotides 1995, 14, 1133-1144. (b) Perrin, K. A.; Huang, J.; McElroy, E. B.; Iams, K. P.; Widlanski, T. S. J. Am. Chem. Soc. 1994, 116, 7427-7428. (c) Strauss, J. K.; Maher, L. J. Science 1994, 266, 1829-1834. (d) Duggan, L. J.; Hill, T. M.; Wu, S.; Garrison, K.; Zhang, X.; Gottlieb, P. A. J. Biol. Chem. 1995, 270, 28049-28054.
30. See, e.g.: (a) Gait, M. J.; Grasby, J. A.; Karn, J.; Mersmann, K.; Pritchard, C. E. Nucleosides Nucleotides 1995, 14, 1133-1144. (b) Perrin, K. A.; Huang, J.; McElroy, E. B.; Iams, K. P.; Widlanski, T. S. J. Am. Chem. Soc. 1994, 116, 7427-7428. (c) Strauss, J. K.; Maher, L. J. Science 1994, 266, 1829-1834. (d) Duggan, L. J.; Hill, T. M.; Wu, S.; Garrison, K.; Zhang, X.; Gottlieb, P. A. J. Biol. Chem. 1995, 270, 28049-28054.
31. See, e.g.: (a) Gait, M. J.; Grasby, J. A.; Karn, J.; Mersmann, K.; Pritchard, C. E. Nucleosides Nucleotides 1995, 14, 1133-1144. (b) Perrin, K. A.; Huang, J.; McElroy, E. B.; Iams, K. P.; Widlanski, T. S. J. Am. Chem. Soc. 1994, 116, 7427-7428. (c) Strauss, J. K.; Maher, L. J. Science 1994, 266, 1829-1834. (d) Duggan, L. J.; Hill, T. M.; Wu, S.; Garrison, K.; Zhang, X.; Gottlieb, P. A. J. Biol. Chem. 1995, 270, 28049-28054.
32. See, e.g.: (a) Gait, M. J.; Grasby, J. A.; Karn, J.; Mersmann, K.; Pritchard, C. E. Nucleosides Nucleotides 1995, 14, 1133-1144. (b) Perrin, K. A.; Huang, J.; McElroy, E. B.; Iams, K. P.; Widlanski, T. S. J. Am. Chem. Soc. 1994, 116, 7427-7428. (c) Strauss, J. K.; Maher, L. J. Science 1994, 266, 1829-1834. (d) Duggan, L. J.; Hill, T. M.; Wu, S.; Garrison, K.; Zhang, X.; Gottlieb, P. A. J. Biol. Chem. 1995, 270, 28049-28054.
33. Baeschlin, D. K.; Hyrup, B.; Benner, S. A.; Richert, C. Unpublished results.
34. Barone, A. D.; Tang, J.-Y.; Caruthers, M. H. Nucleic Acids Res. 1984, 12, 4051-4061.
35. Egholm, M.; Nielsen, P.; Buchardt, O.; Berg, R. H. J. Am. Chem. Soc. 1992, 114, 9677-9678.