Solid-phase synthesis of positively charged deoxynucleic guanidine (DNG) modified oligonucleotides containing neutral urea linkages: Effect of charge deletions on binding and fidelity

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 8, 2000, Pages 1893-1901

  Linkletter, Barry A ^a   Bruice, Thomas C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEMENTARY DNA; DEOXYNUCLEIC GUANIDINE; DEOXYRIBONUCLEOTIDE; GUANIDINE; OLIGONUCLEOTIDE; UNCLASSIFIED DRUG; UREA;

ARTICLE; BASE PAIRING; BINDING AFFINITY; CONTROLLED STUDY; DNA BINDING; DNA DENATURATION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MELTING POINT; NONHUMAN; TEMPERATURE;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; DNA; GUANIDINES; MOLECULAR STRUCTURE; NUCLEIC ACID DENATURATION; OLIGONUCLEOTIDES; TEMPERATURE; UREA;

EID: 0033863248     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(00)00146-2     Document Type: Article

References (30)

1. Agrawal S., Zhao Q.Y. Curr. Opin. Chem. Biol. 2:1998;519.
2. Temsamani J.G.P. Biotech. Appl. Biochem. 26:1997;65.
3. De Mesmaeker A., Häner R., Martin P., Moser H.E. Acc. Chem. Res. 28:1995;366.
4. De Mesmaeker A., Waldner A., Lebreton J., Hoffmann P., Fritsch V., Wolf R.M., Freier S.M. Angew. Chem., Int. Ed. Engl. 33:1994;226.
5. Tseng B.Y., Ts'o P.O.P. Antisense Res. Dev. 5:1995;251.
6. Waldner, A.; De Mesmaeker, A.; Lebreton, J.; Fritsch, V.; Wolf, R. M. Synlett 1994, 57.
7. Morvan F., Sangvhi Y.S., Perbost M., Vasseur J.-J., Bellon L. J. Am. Chem. Soc. 118:1996;255.
8. von Matt P., Altmann K.-H. Bioorg. Med. Chem. Lett. 7:1997;1553.
9. Wang J., Matteucci M.D. Bioorg. Med. Chem. Lett. 7:1997;229.
10. Nielsen P.E. Pure Appl. Chem. 70:1998;105.
11. Uhlmann E., Peyman A., Breipohl G., Will D.W. Angew. Chem., Int. Ed. Engl. 37:1998;2796.
12. Peyman A., Uhlmann E., Wagner K., Augustin S., Breipohl G., Will D.W., Schäfer A., Wallmeier H. Angew. Chem., Int. Ed. Engl. 35:1996;2636.
13. Fujii M., Yoshida K., Hidaka J. Bioorg. Med. Chem. Lett. 7:1997;637.
14. Ueno Y., Mikawa M., Matsuda A. Bioconjugate Chem. 9:1998;33.
15. Skibo E.B., Xing C. Biochemistry. 37:1998;15199.
16. Dempcy R.O., Almarsson Ö., Bruice T.C. Proc. Natl. Acad. Sci. USA. 91:1994;7864.
17. Barawkar D.A., Linkletter B., Bruice T.C. Bioorg. Med. Chem. Lett. 8:1998;1517.
18. Huang C.Y., Uno T., Murphy J.E., Lee S., Hamer J.D., Escobedo J.A., Cohen F.E., Radhakrishnan R., Qwarki V., Zuckermann R.N. Chem. Biol. 5:1998;345.
19. Dempcy R.O., Browne K.A., Bruice T.C. Proc. Natl. Acad. Sci. USA. 92:1995;6097.
20. Dempcy R.O., Browne K.A., Bruice T.C. J. Am. Chem. Soc. 117:1995;6140.
21. Barawkar D.A., Bruice T.C. Proc. Natl. Acad. Sci. USA. 95:1998;11047.
22. Linkletter B.A., Szabo I.E., Bruice T.C. J. Am. Chem. Soc. 121:1999;3888.
23. Just, G.; Grozinger, K. Synthesis 1976, 457.
24. Ernst, S.; Richter, C.; Hobert, A.; Mariam, G. G.; Schulze, K. J. Heterocycl. Chem. 1995, 32, 275.
25. Ullas, G. V.; Chu, C. K.; Ahn, M. K.; Kosugi, Y. J. Org. Chem. 1998, 53, 2413.
26. Waldner, A.; De Mesmaeker, A.; Lebreton, J.; Fritsch, V.; Wolf, R. M. Synlett, 1994, 57.
27. Luo J., Bruice T.C. J. Am. Chem. Soc. 120:1998;1115.
28. Masunov A., Dannenberg J.J. J. Phys. Chem. A. 103:1999;178.
29. Job P. Ann. Chim. 9:1928;113.
30. Blaskó A., Dempcy R.O., Minyat E.E., Bruice T.C. J. Am. Chem. Soc. 118:1996;7892.