On the formation of longmers in phosphorothioate oligodeoxyribonucleotide synthesis

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3875-3878

  Krotz, Achim H ^a   Klopchin, Patrick G ^a   Walker, Kathleen L ^a   Srivatsa, G Susan ^a   Cole, Douglas L ^a   Ravikumar, Vasulinga T ^a  

^a ISIS PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGODEOXYNUCLEOTIDE PHOSPHOROTHIOATE; OLIGODEOXYRIBONUCLEOTIDE; PHOSPHOROTHIOIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0030961842     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00798-3     Document Type: Article

References (14)

1. Crooke, S. T. in Burger's Medicinal Chemistry and Drug Discovery, Vol. 1 (Ed.: M. E. Wolff), Wiley, 1995, pp. 863-900 and references therein.
2. Kisner, D. L. 12th International Roundtable on Nucleosides and Nucleotides, September 19, 1996, La Jolla, CA, USA.
3. (a) McBride, L. C.; Caruthers, M. H. Tetrahedron Lett. 1983, 24, 245;
4. (b) For reviews see: Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311;
5. (c) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123-6194.
6. Ravikumar, V. T.; Andrade, M.; Wyrzykiewicz, T. K.; Scozzari, A.; Cole, D. L. Nucleosides & Nucleotides 1995, 14, 1219-1226.
7. Large scale synthesizers Pharmacia OligoProcess (Pharmacia, Sweden) allow complete synthesis of a 20-mer phosphorothioate oligonucleotide at 0.1 mol scale in 18 h.
8. Köster, H.; Sinha, N. D. Process for the Preparation of Oligonucleotides, United States Patent 4,725,677, February 16, 1988.
9. Krotz, A. H.; Klopchin, P.; Cole, D. L.; Ravikumar, V. T. Bioorg. Med. Chem. Letters 1997, 7, 73-78.
10. Sproat, B.; Colonna, F.; Mullah, B.; Tsou, D.; Andrus A.; Hampel, A.; Vinayak, R. Nucleosides & Nucleotides 1995, 14, 255-273.
11. Lieber, E.; Enkoji, T. J. Org. Chem. 1961, 26, 4472-4479.
12. (a) Brill, W. K.-D.; Nielsen, J.; Caruthers, M. H. J. Am. Chem. Soc. 1991, 113, 397.2-3980.
13. (b) Pieken, W. Oligonucleotides as Therapeutic Agents, January 9, 1997, London, England.
14. 2O, gradient: 0-15 min: 2 to 98% A, 15 to 25 min: 98% A, λ = 254 nm.