Skip to main content
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1996 Sep 15;24(18):3643–3644. doi: 10.1093/nar/24.18.3643

Efficient introduction of phosphorothioates into RNA oligonucleotides by 3-ethoxy-1,2,4-dithiazoline-5-one (EDITH).

Q Xu 1, G Barany 1, R P Hammer 1, K Musier-Forsyth 1
PMCID: PMC146137  PMID: 8836195

Abstract

We recently reported on the use of 1,2,4-dithiazolidine-3,5-dione (DtsNH) and 3-ethoxy-1,2,4-dithiazoline-5-one (EDITH) as effective sulfurizing reagents for the preparation of phosphorothioate-containing oligodeoxyribo-nucleotides [Xu et al. (1996) Nucleic Acids Res., 24, 1602-1607]. One challenge in automated solid-phase synthesis of phosphorothioate-containing RNA is to develop sulfurization reagents that are effective in the presence of bulky 2'-OH protecting groups. The present study demonstrates that EDITH is exceedingly effective at low concentrations (0.05 M) and short reaction times (2 min) for the automated synthesis of oligoribonucleotides.

Full Text

The Full Text of this article is available as a PDF (39.4 KB).

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Bourque A. J., Cohen A. S. Quantitative analysis of phosphorothioate oligonucleotides in biological fluids using fast anion-exchange chromatography. J Chromatogr. 1993 Jul 23;617(1):43–49. doi: 10.1016/0378-4347(93)80419-5. [DOI] [PubMed] [Google Scholar]
  2. Christoffersen R. E., Marr J. J. Ribozymes as human therapeutic agents. J Med Chem. 1995 Jun 9;38(12):2023–2037. doi: 10.1021/jm00012a001. [DOI] [PubMed] [Google Scholar]
  3. Crooke R. M., Graham M. J., Cooke M. E., Crooke S. T. In vitro pharmacokinetics of phosphorothioate antisense oligonucleotides. J Pharmacol Exp Ther. 1995 Oct;275(1):462–473. [PubMed] [Google Scholar]
  4. Eckstein F., Gish G. Phosphorothioates in molecular biology. Trends Biochem Sci. 1989 Mar;14(3):97–100. doi: 10.1016/0968-0004(89)90130-8. [DOI] [PubMed] [Google Scholar]
  5. Eckstein F. Nucleoside phosphorothioates. Annu Rev Biochem. 1985;54:367–402. doi: 10.1146/annurev.bi.54.070185.002055. [DOI] [PubMed] [Google Scholar]
  6. Eguchi Y., Itoh T., Tomizawa J. Antisense RNA. Annu Rev Biochem. 1991;60:631–652. doi: 10.1146/annurev.bi.60.070191.003215. [DOI] [PubMed] [Google Scholar]
  7. Scaringe S. A., Francklyn C., Usman N. Chemical synthesis of biologically active oligoribonucleotides using beta-cyanoethyl protected ribonucleoside phosphoramidites. Nucleic Acids Res. 1990 Sep 25;18(18):5433–5441. doi: 10.1093/nar/18.18.5433. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Wincott F., DiRenzo A., Shaffer C., Grimm S., Tracz D., Workman C., Sweedler D., Gonzalez C., Scaringe S., Usman N. Synthesis, deprotection, analysis and purification of RNA and ribozymes. Nucleic Acids Res. 1995 Jul 25;23(14):2677–2684. doi: 10.1093/nar/23.14.2677. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Xu Q., Musier-Forsyth K., Hammer R. P., Barany G. Use of 1,2,4-dithiazolidine-3,5-dione (DtsNH) and 3-ethoxy-1,2,4-dithiazoline-5-one (EDITH) for synthesis of phosphorothioate-containing oligodeoxyribonucleotides. Nucleic Acids Res. 1996 May 1;24(9):1602–1607. doi: 10.1093/nar/24.9.1602. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Nucleic Acids Research are provided here courtesy of Oxford University Press

RESOURCES