Nucleoside recovery in DNA and RNA synthesis

Tetrahedron Letters

Volumn 40, Issue 51, 1999, Pages 8971-8974

  Wang, Weimin ^a   Song, Quanlai ^a   Jones, Roger A ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; NUCLEOSIDE; PHOSPHONIC ACID DERIVATIVE; POLYOL; RNA;

ARTICLE; DNA SYNTHESIS; ESTERIFICATION; RNA SYNTHESIS;

EID: 0033579581     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01914-0     Document Type: Article

References (8)

1. Troev, K.; Borisov, G. Phosphorus and Sulfur 1987, 29, 129-145.
2. Froehler, B. C. Oligodeoxynucleotide synthesis: H-phosphonate approach. In Protocols for Oligonucleotides and Analogs; Agrawal, S., Ed.; Humana Press: Totowa, NJ, 1993; Vol. 20; pp. 63-80.
3. Huss, S.; Gosselin, G.; Stawinski, J.; Strömberg, R.; Imbach, J.-L. Nucleosides and Nucleotides 1988, 7, 321-337.
4. Brill, W. K.-D. Tetrahedron Lett. 1994, 35, 3041-3044.
5. Song, Q.; Wang, W.; Fischer, A.; Zhang, X.; Gaffney, B. L.; Jones, R. A. Tetrahedron Lett. 1999, 40, 4153-4156.
6. Reese, C. B.; Visintin, C. Tetrahedron Lett. 1999, 40, 6477-6480.
7. 4) and evaporated. The residue was purified by flash chromatography on silica gel (ethyl acetate:dichloromethane (0:100-40:60 v/v) for RNA products, methanol:dichloromethane (0:100-5:95 v/v) for DNA products), to give the nucleosides 4 as pure colorless solids in yields of 85 to 95%.
8. The general procedure for deoxynucleosides was: To 0.5 mmol of 1 in 6 mL dry acetonitrile was added 5 mmol of tetrazole. The mixture was shaken for 5 min, and then injected by syringe into a solution of 0.5 mL glycerol or ethylene glycol in 4 mL of dry acetonitrile with stirring, making a final 5% alcohol solution (v/v). After 5 min, 0.5 mL of pyridine was added, and the reaction solution was stirred for 8 h. Dichloromethane (25 mL) was added, and the mixture was washed twice with 25 mL of phosphate buffer (0.5 M, pH 7.0). The organic layer was evaporated, and the residue was purified by flash chromatography on silica gel using methanol:dichloromethane (gradient: 0:100 to 5:95), to give the deoxynucleosides 4 as pure colorless solids in the same high yields as the two-step procedure.