Synthesis and deprotection of oligonucleotides under aprotic conditions

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3691-3694

  Chen, Tongqian ^a   Fu, Jiasheng ^a   Greenberg, Marc M ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; OLIGONUCLEOTIDE;

ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; SYNTHESIS;

INDICATORS AND REAGENTS; OLIGONUCLEOTIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 0034676580     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006604p     Document Type: Article

References (19)

1. (a) Iyer, R. P.; Beaucage, S. I. In Comprehensive Natural Products Chemistry. Vol. 7; Kool, E. T., Ed.; Elsevier: Amsterdam, 1999; 105.
2. (b) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123.
3. (c) Greenberg, M. M. Chem. Res. Toxicol. 1998, 11, 1235.
4. a) Greenberg, M. M.; Barvian, M. R.; Cook, G. P.; Goodman, B. K.; Malray, T. J.; Tronche, C.; Venkatesan, H. J. Am. Chem. Soc. 1997, 119, 1828.
5. (b) Greenberg, M. M.; Matray, T. J. Biochemistry 1997, 36, 14071.
6. (c) Sambandam, A.; Greenberg, M. M. Nucleic Acids Research 1999, 27, 3597.
7. Scaringe, S. A.; Wincott, F. E.; Carruthers, M. H. J. Am. Chem. Soc. 1998, 120, 11820.
8. (a) Hayakawa, Y.; Kataoka, M. J. Am. Chem. Soc. 1998, 120, 12395.
9. (b) Gryaznov, S. M.; Letsinger, R. L. J. Am. Chem. Soc. 1991, 113, 5876.
10. (a) Hayakawa, Y.; Wakabayashi, S.; Kato, H.; Noyori, R. J. Am. Chem. Soc. 1990, 112, 1691.
11. (b) Stutz, A.; Pitsch, S. Synlett 1999, 930.
12. (c) Hayes, J. A.; Brunden, M. J.; Gilham, P. T.; Gough, G. R. Tetrahedron Lett. 1985, 26, 2407.
13. (a) Himmelsbach, F.; Schulz, B. S.; Trichtinger, T.; Charubala, R.; Pfleiderer, W. Tetrahedron 1984, 40, 59.
14. (b) Stengele, K.-P.; Pfleiderer, W. Tetrahedron Lett. 1990, 31, 2549.
15. Manoharan, M.; Prakash, T. P.; Barber-Peoc'h, I.; Bhat, B.; Vasquez, G.; Ross, B. S.; Cook, P. D. J. Org. Chem. 1999, 64, 6468.
16. Small amounts of a product ascribed to the nucleophilic addition of deoxyguanosine to acrylonitrile were observed during the deprotection of the monomer.
17. Tallman, K. A. Ph.D. Dissertation, Colorado State University, Ft. Collins, CO, 2000.
18. Venkatesan, H.; Greenberg, M. M. J. Org. Chem. 1996, 61, 525. The alkylamine-derivatized polystyrene support was manufactured by Amersham Pharmacia Biotech.
19. Dahl, B. J.; Bjergarde, K.; Henriksen, L.; Dahl, O. Acta Chem. Scand. 1990, 44, 639.