Optimized synthesis of phosphorothioate oligodeoxyribonucleotides substituted with a 5'-protected thiol function and a 3'-amino group

Nucleic Acids Research

Volumn 28, Issue 3, 2000, Pages 818-825

  Aubert, Yves ^a   Bourgerie, Sylvain ^a   Meunier, Laurent ^a   Mayer, Roger ^a   Roche, Annie Claude ^a   Monsigny, Michel ^a   Thuong, Nguyen T ^a   Asseline, Ulysse ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; FLUORESCEIN ISOTHIOCYANATE; METHANOL; OLIGODEOXYNUCLEOTIDE PHOSPHOROTHIOATE; PHENOL; SIGNAL PEPTIDE; THIOL GROUP;

ARTICLE; NUCLEIC ACID SYNTHESIS; OXIDATION; PRIORITY JOURNAL;

EID: 0034142362     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/28.3.818     Document Type: Article

References (39)

1. Stephenson,M.L. and Zamecnik,P.C. (1978) Proc. Natl Acad. Sci. USA, 75, 285-288.
2. Neidle,S. (1997) Anticancer Drug Des., 12, 433-442.
3. Giovannangeli,C. and Hélène,C. (1997) Antisense Nucleic Acid Drug Dev., 7, 413-421.
4. Soyfer,V.N. and Potoman,V.N. (1996) In Garber,R.C. (ed.), Triple-Helical Nucleic Acids. Springer Verlag, New York, NY.
5. Freier,S.M. and Altmann,K.-H. (1997) Nucleic Acids Res., 25, 4429-4443.
6. Wyman,T.B., Nicol,F., Zelphati,O., Scario,P.V., Plank,C. and Szoka,F.C. (1997) Biochemistry, 36, 3008-3017.
7. Wadhwa,M.S., Collard,W.T., Adami,R.C., McKenzie,D.L. and Rice,K.G. (1997) Bioconjugate Chem., 8, 81-88.
8. Morris,M.C., Vidal,P., Chaloin,L., Heitz,F. and Divita,G. (1997) Nucleic Acids Res., 25, 2730-2736.
9. Eritja,R., Pons,A., Escarceller,M., Giralt,E. and Albericio,F. (1991) Tetrahedron Lett., 47, 4113-4120.
10. Arar,K., Monsigny,M. and Mayer,R. (1993) Tetrahedron Lett., 34, 8087-8090.
11. Bongartz,J.P., Aubertin,A.M., Milhaud,P.G. and Lebleu,B. (1994) Nucleic Acids Res., 22, 49-56.
12. Arar,K., Aubertin,A.-M., Roche,A.-C., Monsigny,M. and Mayer,R. (1995) Bioconjugate Chem., 6, 573-577.
13. Soukchareun,S., Tregear,G.W. and Haralambidis,J. (1995) Bioconjugate Chem., 6, 43-53.
14. Pichon,C., Arar,K., Stewart,A.J., DucDodon,M., Gazzolo,L., Courtoy,P.J., Mayer,R., Monsigny,M. and Roche,A.-C. (1996) Mol. Pharmacol., 51, 431-438.
15. Prochiantz,A. (1996) Curr. Opin. Neurobiol., 6, 629-634.
16. Vives,E. and Lebleu,B. (1997) Tetrahedron Lett., 38, 1183-1186.
17. Tung,C.-H., Wang,J., Leibowitz,M.J. and Stein,S. (1995) Bioconjugate Chem., 6, 292-295.
18. Jensen,O.N., Kulkami,S., Aldrich,J.V. and Barofsky,D.F. (1996) Nucleic Acids Res., 24, 3866-3872.
19. Haralambidis,J., Duncan,L., Angus,K. and Tregear,G.W. (1987) Tetrahedron Lett., 28, 5199-5202.
20. Truffert,J.-C., Asseline,U., Brack,A. and Thuong,N.T. (1996) Tetrahedron, 52, 3005-3016.
21. Peyrottes,S., Mestre,B., Burlina,F. and Gait,M.J. (1998) Tetrahedron, 54, 12513-12522.
22. Agrawal,S. and Zamecnik,P.C. (1990) Nucleic Acids Res., 18, 5419-5423.
23. Asseline,U., Bonfils,E., Kurfürst,R., Chassignol,M., Roig,V. and Thuong,N.T. (1992) Tetrahedron, 48, 1233-1254.
24. Nelson,P.S., Frye,R.A. and Liu,E. (1989) Nucleic Acids Res., 17, 7187-7194.
25. Asseline,U. and Thuong,N.T. (1990) Tetrahedron Lett., 31, 81-84.
26. Petrie,C., Reed,M., Adams,A. and Meyer,R. (1992) Bioconjugate Chem., 3, 85-87.
27. Connolly,B.A. (1985) Nucleic Acids Res., 13, 4485-4502.
28. Ansorge,W., Sproat,B., Stegemann,J., Schwager,C. and Zenke,M. (1987) Nucleic Acids Res., 15, 4593-4602.
29. Gaur,R.K., Sharma,P., Kumar,P. and Gupta,K.C. (1989) Nucleic Acids Res., 17, 4404.
30. Kuijpers,W. and van Boeckel,C.A. (1993) Tetrahedron, 49, 10931-10944.
31. Sorger,P.K. and Pelham,H.R.B. (1987) J. Mol. Biol., 194, 341-344.
32. Atkinson,T. and Smith,M. (1984) In Gait,M.J. (ed.), Oligonucleotides Synthesis: A Practical Approach. IRL Press, Oxford, UK, pp. 35-81.
33. Puglisi,J.D. and Tinocco,I. (1989) Methods Enzymol., 180, 304-325.
34. Beaucage,S. and Caruthers,M. (1981) Tetrahedron Lett., 20, 94-102.
35. Iyer,R., Egan,W., Regan,J. and Beaucage,S. (1990) J. Am. Chem. Soc., 112, 1253-1254.
36. Carlsson,J., Drevin,H. and Axen,R. (1987) Biochem. J., 173, 723-737.
37. Smith,L.M., Fung,S., Hunkapiller,M.W., Hunkapiller,T. and Hood,L.E. (1985) Nucleic Acids Res., 13, 2399-2412.
38. Burns,J.A., Bulter,J.C., Moran,J. and Whitesides,G.M. (1991) J. Org. Chem., 56, 2648-2650.
39. Fidanza,J.A., Ozaki,H. and McLaughlin,L. (1994) In Agrawal,S. (ed.), Protocols for Oligonucleotide Conjugates. Synthesis and Analytical Techniques. Humana Press, Totowa, NJ, pp. 121-143.