Synthesis of metal-chelating deoxycytidine-analogue phosphoramidites for the automatic synthesis of labelled oligonucleotides

Synthesis

Volumn , Issue 11, 2004, Pages 1835-1843

  Giordano, Cesare ^a   Del Bianco, Cristina ^b   Faini, Sara ^b   Napoli, Anna ^c   Sindona, Giovanni ^c   Cellai, Luciano ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF CALABRIA   (Italy)

Author keywords

Chelates; DNA; Footprinting; Nucleosides; Oligonucleotides

Indexed keywords

AMINO ACIDS; ESTERS; METALS; SYNTHESIS (CHEMICAL);

DEOXYCYTIDINE (DC); PHOSPHORAMIDITES;

CHELATION;

5' O (4,4' DIMETHOXYTRITYL) N4 [2 [2 [[2 BIS(ETHOXYCARBONYLMETHYLAMINO)ETHYL]ETHOXYCARBONYLMETHYLAMINO]ACETYLAMINO]ETHYL] 2' DEOXYCYTIDINE 3' O (2 CYANOETHYL) N,N DIISOPROPYLPHOSPHORAMIDITE; 5' O (4,4' DIMETHOXYTRITYL) N4 [4 [2 [[2 BIS(ETHOXYCARBONYLMETHYLAMINO)ETHYL]ETHOXYCARBONYLMETHYLAMINO]ACETYLAMINO]CYCLOHEXYL] 2' DEOXYCYTIDINE 3' O (2 CYANOETHYL) N,N DIISOPROPYLPHOSPHORAMIDITE; 5' O (4,4' DIMETHOXYTRITYL) N4 [4 [N,N BIS [2 [BIS(2 ETHOXYCARBONYLMETHYLAMINO)ETHYL]ETHOXYCARBONYLMETHYLAMINO]ACETYLAMINO]CYCLOHEXYL] 2' DEOXYCYTIDINE 3' O (2 CYANOETHYL) N,N DIISOPROPYLPHOSPHORAMIDITE; 5' O (4,4' DIMETHOXYTRITYL) N4 [6 [2 [[2 BIS(ETHOXYCARBONYLMETHYLAMINO)ETHYL]ETHOXYCARBONYLMETHYLAMINO]ACETYLAMINO]HEXYL] 2' DEOXYCYTIDINE 3' O (2 CYANOETHYL) N,N DIISOPROPYLPHOSPHORAMIDITE; CHELATING AGENT; CYTIDINE DERIVATIVE; OLIGODEOXYNUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DNA FOOTPRINTING; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 4043141672     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829143     Document Type: Article

References (26)

1. Meares, C. F.; Wensel, T. G. Acc. Chem. Res. 1984, 17, 202.
2. Rebizac, R.; Schaefer, M.; Dellacherie, E. Bioconjugate Chem. 1998, 9, 94.
3. Montembault, V.; Soutif, J.-C.; Brosse, J.-C.; Hindrè, F.; Le Joune, J.-J. React. Funct. Polym. 1997, 32, 43; Chem. Abstr. 1997, 126, 154510.
4. Montembault, V.; Soutif, J.-C.; Brosse, J.-C.; Hindrè, F.; Le Joune, J.-J. React. Funct. Polym. 1997, 32, 43; Chem. Abstr. 1997, 126, 154510.
5. Martin, V. V.; Ralston, W. H.; Hynes, M. R.; Keana, J. F. W. Bioconjugate Chem. 1995, 6, 616.
6. Meares, C. F.; De Riemer, L. H.; Goodwin, D. A. In Bleomycin: Chemical, Biochemical and Biological Aspects; Hecht, S. M., Ed.; Springer-Verlag: Berlin, 1979, 309-323.
7. Critical Stability Constants, Vol. 1; Martel, A. E.; Smith, R. M., Eds.; Plenum: New York, 1974.
8. Taylor, J. S.; Schultz, P. J.; Dervan, P. B. Tetrahedron 1984, 40, 457.
9. Herzberg, R. P.; Dervan, P. B. Biochemistry 1984, 23, 3934.
10. Schultz, P. J.; Dervan, P. B. J. Biomol. Struct. Dyn. 1984, 1, 1133.
11. Schultz, P. J.; Dervan, P. B. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 6834.
12. Schultz, P. J.; Taylor, J. S.; Dervan, P. B. J. Am. Chem. Soc. 1982, 104, 6861.
13. Herzberg, R. P.; Dervan, P. B. J. Am. Chem. Soc. 1982, 104, 313.
14. Iwahara, J.; Anderson, D. E.; Murphy, E. C.; Clore, G. M. J. Am. Chem. Soc. 2003, 125, 6634.
15. Dryer, G. B.; Dervan, P. B. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 968.
16. Giordano, C.; Fratini, F.; Attanasio, D.; Cellai, L. Synthesis 2001, 565.
17. Hay, R. V.; Nolan, K. B. J. Chem. Soc., Dalton Trans. 1975, 1348.
18. Smith, J.; Liras, J. L.; Schneider, S. E.; Anslyn, E. V. J. Org. Chem. 1996, 61, 8811.
19. Roget, A.; Bazin, H.; Teoule, R. Nucleic Acid Res. 1989, 17, 7643.
20. Burks, E.; Koshti, N.; Jacobs, H.; Gopalan, A. Synlett 1998, 1285.
21. Roy, B. C.; Mallik, S. Org. Lett. 2001, 3, 1877.
22. Adamczyk, M.; Fishpaugh, J. R.; Heuser, K. J. Org. Prep. Proced. Int. 1998, 30, 339.
23. Gustaffson, J.; Haerd, T. Biochemistry 1993, 32, 13463.
24. Coffin, J. M.; Hughes, S. H. In Retroviruses; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, 1997.
25. Perrin, D. D.; Armarego, L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: London, 1988.
26. Schmitt-Willich, H.; Olatzek, J.; Niedballa, U.; Raduechel, B.; Muehler, A.; Frenzel, T.; Ebert, W. Ger. Offen. DE 4425857, 1996; Chem. Abstr. 1996, 124, 232789.