Oligonucleoside phosphoramidates from N-pent-4-enoyl nucleoside H-phosphonates

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1543-1546

  Iyer, Radhakrishnan P ^a   Devlin, Theresa ^a   Habus, Ivan ^a   Yu, Dong ^a   Johnson, Suzanne ^a   Agrawal, Sudhir ^a  

^a HYBRIDON INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0030000395     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00067-6     Document Type: Article

References (11)

1. For reviews see: (a) Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 544-584;
2. (b) Agrawal, S, Iyer, R. P. Curr. Op. Biotech. 1995, 6, 12-19;
3. (c) Agrawal, S.; Temsamani, J.; Galbraith, W.; Tang, J. Clin. Pharmacokinet. 1995, 28, 7-16.
4. (a) Froehler, B. C. Tetrahedron Lett. 1986, 27, 5575-78;
5. (b) Agrawal, S.; Goodchild, J.; Civiera, M. P.; Thornton, A. H.; Sarin, P. S.; Zamecnik, P. C. Proc. Natl. Acad. Sci. USA, 1988, 85, 7079-83.
6. Harger, M. J. P. J. Chem. Soc. Chem. Commun. 1976, 555-56.
7. Shabarova, Z.; Bogdanova, A. Advanced Organic Chemistry of Nucleic Acids, VCH Publishers Inc.: New York, 1994; pp. 169-180.
8. For application of PNT nucleosides in phosphoramidite chemistry, see Iyer, R. P.; Yu, D.; Ho, N-H.; Devlin, T.; Agrawal S. J. Org. Chem, 1995, 60, 8132-33.
9. Iyer, R. P.; Devlin, T.; Habus, I., Ho, N-H.; Yu, D.; Agrawal, S. Tetrahedron Lett. (preceding paper).
10. For details of HPLC conditions and analysis, see Iyer, R. P.; Yu, D.; Agrawal, S. Bioorg. Chem. 1995, 23, 1-21.
11. The 5′-DMT group is conveniently removed by brief treatment using Dowex® see Iyer, R. P.; Jiang, Z.; Yu, D.; Tan, W.; Agrawal, S. Synth. Commun. 1995, 25, 3611-3623.