Preparation of C8-amine and acetylamine adducts of 2′-deoxyguanosine suitably protected for DNA synthesis

Organic Letters

Volumn 4, Issue 24, 2002, Pages 4205-4208

  Gillet, Ludovic C J ^a   Schärer, Orlando D ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DEOXYGUANOSINE; DNA; DRUG DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMINES; DEOXYGUANOSINE; DNA; MOLECULAR STRUCTURE;

EID: 0037191621     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026474f     Document Type: Article

References (32)

1. (a) Heflich, R. H.; Neft, R. E. Mut. Res. 1994, 318, 73-174.
2. (b) Schut, H. A. J.; Snyderwine, E. G. Carcinogenesis 1999, 20, 353-368.
3. (c) Heflich, R. H.; Howard, P. C.; Beland, F. A. Mut. Res. 1985, 149, 25-32.
4. O'Handley, S. F.; Sanford, D. G.; Xu, R.; Lester, C. C.; Hingerty, B. E.; Broyde, S.; Krugh, T. R. Biochemistry 1993, 52, 2481-2497.
5. (a) van Oosterwijk, M. F.; Filon, R.; de Groot, A. J. L.; van Zeeland, A. A.; Mullenders, L. H. F. J. Biol. Chem. 1998, 273, 13599-13604.
6. (b) Shibutani, S.; Suzuki, N.; Grollman, A. P. Biochemistry 1998, 37, 12034-12041.
7. (a) Gunz, D.; Hess, M. T.; Naegeli, H. J. Biol. Chem. 1996, 271, 25089-25098.
8. (b) Batty, D. P.; Wood, R. D. Gene 2000, 241, 193-204.
9. Stöhrer, G.; Osband, J. A.; Alvarado-Urbina, G. Nucleic Acids Res. 1983, 11, 5093-5101.
10. Zhou, Y.; Chladek, S.; Romano, L. J. J. Org. Chem. 1994, 59, 556-563.
11. Zhou, Y.; Romano, L. J. Biochemistry 1993, 32, 14043-14052.
12. (a) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609-3612.
13. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
14. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
15. (d) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144-1157.
16. Lakshman, M. K.; Keeler, J. C.; Hilmer, J. H.; Martin, J. Q. J. Am. Chem. Soc. 1999, 121, 6090-6091.
17. (a) De Riccardis, F.; Bonala, R. R.; Johnson, F. J. Am. Chem. Soc. 1999, 121, 10453-10460.
18. (b) Harwood: E. A.; Hopkins, P. B.; Sigurdsson, S. T. J. Org. Chem. 2000, 65, 2959-2964.
19. Schoffers, E.; Olsen, P. D.; Means, J. C. Org. Lett. 2001, 3, 4221-4223.
20. Wang, Z.; Rizzo, C. J. Org. Lett. 2001, 3, 565-568.
21. Meier, C.; Gräsl, S. Synlett 2002, 802-804.
22. Schulhof, J. C.; Molko, D.; Teoule, R. Nucleic Acids Res. 1987, 397-416.
23. Gannett, P. M.; Sura, T. P. Synth. Com. 1993, 23, 1611-1615.
24. 3 yielded no detectable product or took several days to go to completion.
25. Failure of efficient coupling of acetyl arylamines under similar conditions has been reported previously (Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525-7546. Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35-37).
26. Failure of efficient coupling of acetyl arylamines under similar conditions has been reported previously (Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525-7546. Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35-37).
27. Klaspars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
28. Compound 9 was further successfully converted to its 5′-O-DMTr-3′-O-phosphoramidite derivative using standard methods.
29. These new deprotection conditions have been developed in our laboratory to release oligonucleotides from the ultra-mild Q-supports and to remove all the protecting groups, including the cyanoethyl groups on the phosphates and the ultra-mild exocyclic amino protections on the bases, for oligomers that contained very base labile modifications (Alzeer, J.; Gillet, L. C. J.; Schärer, O. D. Manuscript in preparation).
30. iPrPac group in less than 1 h.
31. iPrPac-protected dG was previously observed during the capping step of standard oligonucleotide synthesis (Zhu, Q.; Delaney, M. O.; Greenberg, M. M. Bioorg. Med. Chem. Lett. 2001, 11, 1105-1107).
32. Our conditions allow the coupling of amines such as p-aminobenzophenone that we found to be too unstable to be activated to their N-hydroxylamine for direct coupling with dG.