Oligo-2'-fluoro-2'-deoxynucleotide N3'→P5' phosphoramidates: Synthesis and properties

Nucleic Acids Research

Volumn 24, Issue 15, 1996, Pages 2966-2973

  Schultz, Ronald G ^a   Gryaznov, Sergei M ^a  

^a ILLUMINA INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; IODINE; NUCLEIC ACID; OLIGODEOXYRIBONUCLEOTIDE; PHOSPHODIESTERASE; PHOSPHORAMIDIC ACID DERIVATIVE; RNA; SNAKE VENOM;

ARTICLE; COMPLEX FORMATION; DNA SYNTHESIS; HYDROLYSIS; OXIDATION; PRIORITY JOURNAL; SYNTHESIS; THERMOSTABILITY;

BASE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; FLUORINE COMPOUNDS; HEAT; HYDROLYSIS; MOLECULAR SEQUENCE DATA; NUCLEIC ACID CONFORMATION; NUCLEIC ACID DENATURATION; OLIGODEOXYRIBONUCLEOTIDES; PYRIMIDINES; RNA;

SERPENTES;

EID: 0030038280     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/24.15.2966     Document Type: Article

References (30)

1. Helene,C. and Toulme,J.-J. (1990) Biochim. Biophys. Acta, 1049, 99-125.
2. Uhlman,E. and Peyman,A. (1990) Chem. Rev., 90, 544-584
3. Bielinska,A., Shivdasami,R.A., Zhang,L. and Nabel,G.J. (1990) Science, 250, 997-101.
4. Wyatt,J.R., Vickers,T.A., Roberson,J.L., Buckheit,R.W.,Jr, Klimkait,J., DeBeats,E., Davis,P.W., Rayner,B., Imbach,J.-L. and Ecker,D.J. (1994) Proc. Natl Acad. Sci. USA, 91, 1356-1360.
5. DeMesmacker,A., Altman,K.-H., Waldner,A. and Wendeborn,S. (1995) Curr Opin. Struct. Biol.,5, 343-355.
6. Gryaznov,S.M. and Chen,J.-K. (1994) J. Am. Chem. Soc., 116, 3143-3144.
7. Gryaznov,S.M., Lloyd,D.H., Chen,J.-K., Schultz,R.G., DeDionisio,L.A., Ratmeyer,L. and Wilson,W.D. (1995) Proc. Natl Acad. Sci. USA, 92, 5798-5802.
8. Chen,J.-K., Schultz,R.G., Lloyd,D.H. and Gryaznov,S.M. (1995) Nucleic Acids Res., 23, 2661-2668.
9. Ding,D., Gryaznov,S.M., Lloyd,D.H., Chandrasekaran,S., Yao,S., Ratmeyer,L., Li Pan,Y. and Wilson,W.D. (1996) Nucleic Acids Res., 24, 354-360.
10. Gryaznov,S. M. and Letsinger,R.L. (1992) Nucleic Acids Res., 20, 3403-3409.
11. Kawasaki,A.M., Casper,M.D., Freier,S.M., Lesnik,E.A., Zounes,M.C., Cummins,L.L., Gonzalez,C. and Cook,P.D. (1993) J. Med. Chem., 36, 831-841.
12. Monia,B.P., Lesnik,EA, Gonzalez,C., Lima,W.F., McGee,D., Guinosso,C.J., Kawasaki,A.M., Cook,P.D. and Freier,S.M. (1993) J. Biol. Chem., 268, 14514-14522.
13. Pieken,W.A., Olsen,D.B., Benseler,F., Aurup,K.H. and Eckstein,F. (1991) Science, 253, 314-317.
14. Ikehara,M. (1984) Heterocycles, 21, 75-90.
15. Guschlbauer,W. and Jankowski,K. (1980) Nucleic Acids Res., 8, 1421-1433.
16. Webb,T.R., Mitsuya,H. and Broder,S. (1988) J. Med. Chem., 31, 1475-1479.
17. Codington,J.F., Fecher,R. and Fox,J.J. (1960) J. Am. Chem. Soc., 82, 2794-2803.
18. Codington,J.F., Fecher,R. and Fox,J.J. (1962) J. Org. Chem., 27, 163-167.
19. Reichman,U., Hollenberg,D.H., Chu,C.K., Watanabe,K.A. and Fox,J.J. (1976) J. Org. Chem., 41, 2042-2043.
20. Divakar,K.J. and Reese,C.B. (1982) J. Chem. Soc. Perkin Trans.,1, 1171-1176.
21. Atkinson,T. and Smith,M. (1984) In Gait,M.J. (ed.), Oligonucleotide Synthesis. A Practical Approach. IRL Press, Oxford, UK, pp. 35-81.
22. Knorr,R., Trzeciak,A., Bannwarth,W. and Gillessen,D. (1989) Tetrahedron Lett.,30, 1927-1930.
23. Bannwarth,W. (1988) Helv. Chem. Acta, 71, 1517-1527.
24. Gryaznov,S.M. and Letsinger,R.L. (1991) J. Am. Chem. Soc., 113, 5876-5877.
25. Gryaznov,S.M. and Letsinger,R.L. (1992) Tetrahedron Lett., 33, 4127-4128.
26. Krug,A., Oretskaya,T.S., Volkov,E.M., Cech,D., Shabarova,Z.A. and Rosenthal,A. (1989) Nucleosides Nucleotides, 8, 1473-1483.
27. Williams,D.M., Beuseler,F. and Eckstein,F. (1991) Biochemistry, 30, 4001-4009.
28. Caruthers,M.H. (1991) Acc. Chem. Res., 24, 278-284.
29. Gryaznov,S.M. and Letsinger,R.L. (1993) Nucleic Acids Res., 21, 1403-1408.
30. Obenland,C.O., Mangold,D.J. and Marino,M.P. (1966) Inorg. Synth., 8, 53-56.