New solid support for the synthesis of 3′-oligonucleotide conjugates through glyoxylic oxime bond formation

Organic Letters

Volumn 9, Issue 2, 2007, Pages 219-222

  Spinelli, Nicolas ^a   Edupuganti, Om Prakash ^a   Defrancq, Eric ^a   Dumy, Pascal ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GLYOXYLIC ACID DERIVATIVE; OLIGONUCLEOTIDE; OXIME; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; STEREOISOMERISM; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; GLYOXYLATES; MOLECULAR STRUCTURE; OLIGONUCLEOTIDES; OXIMES; PEPTIDES; STEREOISOMERISM;

EID: 33846617784     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062607b     Document Type: Article

References (34)

1. Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 543-584.
2. Klinman, D. M. Int. Rev. Immunol. 2006, 25, 135-154.
3. Beaucage, S. L. Curr. Med. Chem. 2001, 8, 1213-1244.
4. Gothelf, K. V.; LaBean, T. H. Org. Biomol. Chem. 2005, 3, 4023-4037.
5. (a) Tung, C. H.; Stein, S. Bioconjugate Chem. 2000, 11, 605-18.
6. (b) Gait, M. J. Cell Mol. Life Sci. 2003, 60, 844-853.
7. (c) Venkatesan, N.; Kim, B. H. Chem. Rev. 2006, 106, 3712-3761.
8. Zatsepin, T. S.; Oretskaya, T. S. Chem. Biodiversity 2004, 1, 1401-1417.
9. Gosse, C.; Boutonne, A.; Aujard, I.; Chami, M.; Kononov, A.; Cogne-Laage, E.; Allemand, J.-F.; Li, J.; Jullien, L. J. Phys. Chem. B 2004, 108, 6485-6497.
10. Grimm, G. N.; Boutonne, A. S.; Lincoln, P.; Nordén, B.; Hélène, C. ChemBioChem 2002, 3, 324-331.
11. (a) Harrison, J. G.; Balasubramanian, S. Nucleic Acids Res. 1998, 26, 3136-3145.
12. (b) Arar, K.; Aubertin, A. M.; Roche, A. C.; Monsigny, M.; Mayer, R. Bioconjugate Chem. 1995, 6, 573-577.
13. (a) Antopolsky, M.; Azhayeva, E.; Tengvall, U.; Auriola, S.; Jaaskelainen, I.; Ronkko, S.; Honkakoski, P.; Urtti, A.; Lonnberg, H.; Azhayev, A. Bioconjugaie Chem. 1999, 10, 598-606.
14. (b) Maurel, F.; Debart, F.; Cavelier, F.; Thierry, A. R.; Lebleu, B.; Vasseur, J. J.; Vives, E. Bioorg. Med. Chem. Lett. 2005, 15, 5084-5087.
15. Zatsepin, T. S.; Stetsenko, D. A.; Gait, M. J.; Oretskaya, T. S. Bioconjugate Chem. 2005, 16, 470-489.
16. (a) Ollivier, N.; Olivier, C.; Gouyette, C.; Huynh-Dinh, T.; GrasMasse, H.; Melnyk, O. Tetrahedron Lett. 2002, 43, 997-999.
17. (b) Raddatz, S.; Mueller-Ibeler, J.; Kluge, J.; Wäss, L.; Burdinski, G.; Havens, J. R.; Onofrey, T. J.; Wang, D.; Schweitzer, M. Nucleic Acids Res. 2002, 30, 4793-4802.
18. (a) Gierlich, J.; Burley, G. A.; Gramlich, P. M. E.; Hammond, D. M.; Carell, T. Org. Lett. 2006, 8, 3639-3642.
19. (b) Bouillon, C.; Meyer, A.; Vidai, S.; Jochum, A.; Chevolot, Y.; Cloarec, J. P.; Praly, J. P.; Vasseur, J. J.; Morvan, F. J. Org. Chem. 2006, 71, 4700-4702.
20. (a) Edupuganti, O. P.; Singh, Y.; Defrancq, E.; Dumy, P. Chem.-Eur. J. 2004, 10, 5988-5995.
21. (b) Zatsepin, T. S.; Stetsenko, D. A.; Arzumanov, A. A.; Romanova, E. A.; Gait, M. J.; Oretskaya, T. S. Bioconjugate Chem. 2002, 13, 822-830.
22. (a) Singh, Y.; Renaudet, O.; Defrancq, E.; Dumy, P. Org. Lett. 2005, 7, 1359-1362.
23. (b) Dey, S.; Sheppard, T. L. Org. Lett. 2001, 3, 3983-3986.
24. (a) Trévisiol, E.; Renard, A.; Defrancq, E.; Lhomme, J. Nucleosides Nucleotides Nucleic Acids 2000, 19, 1427-1439.
25. (b) Salo, H.; Virta, P.; Hakala, H.; Prakash, T. P.; Kawasaki, A. M.; Manoharan, M.; Lönnberg, H. Bioconjugate Chem. 1999, 10, 815-823.
26. Far, S.; Gouyette, C.; Melnyk, O. Tetrahedron 2005, 61, 6138-6142.
27. (a) Liu, H.; Wang, L.; Brock, A.; Wong, C.-H.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 1702-1703.
28. (b) Olivier, C.; Hot, D.; Huot, L.; Ollivier, N.; El-Mahdi, O.; Gouyette, C.; Huynh-Dinh, T.; Gras-Masse, H.; Lemoine, Y.; Melnyk, O. Bioconjugate Chem. 2003, 14, 430-439.
29. Singh, Y.; Defrancq, E.; Dumy, P. J. Org. Chem. 2004, 69, 8544-8546.
30. Aumailley, M.; Gurrath, M.; Muller, G.; Calvete, J.; Timpl, R.; Kessler, H. FEBS Lett. 1991, 291, 50-54.
31. Avino, A.; Guimil Garcia, R.; Albericio, F.; Mann, M.; Wilm, M.; Neubauer, G.; Eritja, R. Bioorg. Med. Chem. 1996, 4, 1649-1658.
32. Pon, R. T. Solid-Phase Supports for Oligonucleotide Synthesis; Humana Press Inc.: Totowa, NJ, 1993; Vol. 20.
33. Forget, D.; Boturyn, D.; Defrancq, E.; Lhomme, J.; Dumy, P. Chem.-Eur. J. 2001, 7, 3970-3984.
34. Trevisiol, E.; Defrancq, E.; Lhomme, J.; Laayoun, A.; Cros, P.; Tetrahedron 2000, 56, 6501-6510.