An improved synthesis of oligodeoxynucleotide N3'→P5' phosphoramidates and their chimera using hindered phosphoramidite monomers and a novel handle for reverse phase purification

Nucleic Acids Research

Volumn 26, Issue 16, 1998, Pages 3813-3824

  Fearon, Karen L ^a   Hirschbein, Bernard L ^a   Nelson, Jeffrey S ^a   Foy, Michael F ^a   Nguyen, Mark Q ^a   Okruszek, Andrzej ^b   McCurdy, Sarah N ^a   Frediani, Jeff E ^a   Dedionisio, Lawrence A ^a   Raible, Annette M ^a   Neil Cagle, E ^a   Boyd, Vicky ^c  

^a ILLUMINA INC   (United States)

^b CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^c APPLIED BIOSYSTEMS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN PEROXIDE; OLIGODEOXYNUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; PYRIDINE; RIBONUCLEOTIDE; WATER;

ARTICLE; CONTROLLED STUDY; DNA PURIFICATION; DNA SYNTHESIS; METHODOLOGY; OXIDATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

AMINES; BASE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; OLIGONUCLEOTIDES, ANTISENSE; ORGANOPHOSPHORUS COMPOUNDS; OXIDATION-REDUCTION;

EID: 18244414259     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/26.16.3813     Document Type: Article

References (25)

1. Uhlman,E. and Peyman,A. (1990) Chem. Rev., 90, 544-584.
2. Kibler-Herzog,L., Zon,G., Uzanski,B., Whitter,G. and Wilson,W.D. (1991) Nucleic Acids Res., 19, 2979-2986.
3. Stein,C.A. and Cheng,Y.-C. (1993) Science, 261, 1004-1012.
4. Altmann,K.-H., Fabbro,D., Dean,N.M., Geiger,T., Monia,B.P., Müller,M. and Nicklin,P. (1996) Biochem. Soc. Transact., 24, 630-637.
5. Shibahara,S., Mukai,S., Nishihara,T., Inoue,H., Ohtsuka,E. and Morisawa,H. (1987) Nucleic Acids Res., 15, 4403-4415.
6. Gryaznov,S. and Chen,J.-K. (1994) J. Am. Chem. Soc., 116, 3143-3144.
7. Chen,J.-K., Schultz,R.G., Lloyd,D.H. and Gryaznov,S.M. (1995) Nucleic Acids Res., 23, 2661-2668.
8. 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.
9. Gryzanov,S., Skorski,T., Cucco,C., Nieborowska-Skorska,M., Chiu,C.Y., Lloyd,D., Chen,J.-K., Koziolkiewicz,M. and Calabretta,B. (1996) Nucleic Acids Res., 24, 1508-1514.
10. Skorski,T., Perrotti,D., Nieborowska-Skorska,M., Gryaznov,S. and Calabretta,B. (1997) Proc. Natl Acad. Sci. USA, 94, 3966-3971.
11. Heidenreich,O., Gryaznov,S. and Nerenberg,M. (1997) Nucleic Acids Res., 25, 776-780.
12. DeDionisio,L. and Gryaznov,S.M. (1995) J. Chromatog. B: Biomed. Appl., 669, 125-131.
13. Escudé,C., Giovannangeli,C., Sun,J.-S., Lloyd,D.H., Chen,J.-K., Gryaznov,S.M, Garestier,T. and Hélène,C. (1996) Proc. Natl Acad. Sci. USA, 93, 4365-4369.
14. Giovannangeli,C., Diviacco,S., Labrousse,V., Gryaznov,S., Charneau,P. and Hélène.C. (1997) Proc. Natl Acad. Sci. USA, 94, 79-84.
15. McCurdy,S.N., Nelson,J.S., Hirschbein,B.L. and Fearon,K.L. (1997) Tetrahedron Lett., 38, 207-210.
16. Nelson,J.S., Fearon,K.L., Nguyen,M.Q., McCurdy,S.N., Frediani,J.E., Foy,M.F. and Hirschbein,B.L. (1997) J. Org. Chem., 62, 7278-7287.
17. Batyeva,É.S., Al'fonsov,V.A., Zamaletdinova,G.U. and Pudovik,A.N. (1976) Zh. Obshch. Khim., 46, 2204-2207.
18. Perrin,D.D. (1965) Dissociation Constants of Organic Bases in Aqueous Solution. London Butterworths, London, pp. 41, 137, 141.
19. Zaitseva,V.E., Skaptsova,N.V., Azhayev,A.V. and Krayevsky,A.A. (1984) Bioorganic Chemistry, Russian, 10, 401-407.
20. Nielsen,J. and Caruthers,M.H. (1988) J. Am. Chem. Soc., 110, 6275-6276.
21. Pon,R.T., Usman,N., Damha,M.J. and Ogilvie,K.K. (1986) Nucleic Adas Res., 14, 6453-6470.
22. Kamimura,T., Tsuchiya,M., Koura,K., Sekine,M. and Hata,T. (1983) Tetrahedron Lett., 24, 2775-2778.
23. Nelson,P.S., Muthini,S., Vierra,M., Acosta,L. and Smith,T.H. (1997) BioTechniques, 22, 752-756.
24. Fearon,K.L., Hirschbein,B.L., Chiu,C.-Y., Quijano,M.R. and Zon,G. (1997) In Chadwick,D.J. and Cardew,G. (eds), Oligonucleotides as Therapeutic Agents. John Wiley and Sons, New York, pp. 19-37.
25. Stec,W.J., Uznanski,B., Wilk,A., Hirschbein,B.L., Fearon,K.L. and Bergot,B.J. (1993) Tetrahedron Lett., 34, 5317-5320.