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. 1988 Aug 11;16(15):7633–7645. doi: 10.1093/nar/16.15.7633

Synthesis of nucleic acid methylphosphonothioates.

H C Roelen 1, E de Vroom 1, G A van der Marel 1, J H van Boom 1
PMCID: PMC338431  PMID: 3412896

Abstract

The reagent obtained in situ by treating methylphosphonothioic dichloride with 1-hydroxy-6-trifluoromethylbenzotriazole could be used for the introduction of methylphosphonothioate linkages. The individual diastereomers of the protected dimer d-Tp(S,Me)A were applied in the synthesis of the chiral pure (R or S) hexamers d-[CpCpTp(S,Me)ApGpG]. The reagent showed also to be very effective for the preparation of the 3',5'-cyclic methylphosphonothioate of uridine.

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Selected References

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

  1. Blake K. R., Murakami A., Miller P. S. Inhibition of rabbit globin mRNA translation by sequence-specific oligodeoxyribonucleotides. Biochemistry. 1985 Oct 22;24(22):6132–6138. doi: 10.1021/bi00343a015. [DOI] [PubMed] [Google Scholar]
  2. Blake K. R., Murakami A., Spitz S. A., Glave S. A., Reddy M. P., Ts'o P. O., Miller P. S. Hybridization arrest of globin synthesis in rabbit reticulocyte lysates and cells by oligodeoxyribonucleoside methylphosphonates. Biochemistry. 1985 Oct 22;24(22):6139–6145. doi: 10.1021/bi00343a016. [DOI] [PubMed] [Google Scholar]
  3. Eckstein F. Nucleoside phosphorothioates. Annu Rev Biochem. 1985;54:367–402. doi: 10.1146/annurev.bi.54.070185.002055. [DOI] [PubMed] [Google Scholar]
  4. Griffiths A. D., Potter B. V., Eperon I. C. Stereospecificity of nucleases towards phosphorothioate-substituted RNA: stereochemistry of transcription by T7 RNA polymerase. Nucleic Acids Res. 1987 May 26;15(10):4145–4162. doi: 10.1093/nar/15.10.4145. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Haeuptle M. T., Frank R., Dobberstein B. Translation arrest by oligodeoxynucleotides complementary to mRNA coding sequences yields polypeptides of predetermined length. Nucleic Acids Res. 1986 Feb 11;14(3):1427–1448. doi: 10.1093/nar/14.3.1427. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. König W., Geiger R. Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexycarbodiimid unter Zusatz von 1-Hydroxy-benzotriazolen. Chem Ber. 1970;103(3):788–798. doi: 10.1002/cber.19701030319. [DOI] [PubMed] [Google Scholar]
  7. Marugg J. E., de Vroom E., Dreef C. E., Tromp M., van der Marel G. A., van Boom J. H. Synthesis of nucleic acid methylphosphonates via the 1-hydroxybenzotriazole phosphotriester approach. Nucleic Acids Res. 1986 Mar 11;14(5):2171–2185. doi: 10.1093/nar/14.5.2171. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Marugg J. E., van den Bergh C., Tromp M., van der Marel G. A., van Zoest W. J., van Boom J. H. Synthesis of phosphorothioate-containing DNA fragments by a modified hydroxybenzotriazole phosphotriester approach. Nucleic Acids Res. 1984 Dec 11;12(23):9095–9110. doi: 10.1093/nar/12.23.9095. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Miller P. S., Annan N. D., McParland K. B., Pulford S. M. Oligothymidylate analogues having stereoregular, alternating methylphosphonate/phosphodiester backbones as primers for DNA polymerase. Biochemistry. 1982 May 11;21(10):2507–2512. doi: 10.1021/bi00539a033. [DOI] [PubMed] [Google Scholar]
  10. Miller P. S., McParland K. B., Jayaraman K., Ts'o P. O. Biochemical and biological effects of nonionic nucleic acid methylphosphonates. Biochemistry. 1981 Mar 31;20(7):1874–1880. doi: 10.1021/bi00510a024. [DOI] [PubMed] [Google Scholar]
  11. Murakami A., Blake K. R., Miller P. S. Characterization of sequence-specific oligodeoxyribonucleoside methylphosphonates and their interaction with rabbit globin mRNA. Biochemistry. 1985 Jul 16;24(15):4041–4046. doi: 10.1021/bi00336a036. [DOI] [PubMed] [Google Scholar]
  12. Noble S. A., Fisher E. F., Caruthers M. H. Methylphosphonates as probes of protein-nucleic acid interactions. Nucleic Acids Res. 1984 Apr 11;12(7):3387–3404. doi: 10.1093/nar/12.7.3387. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Reese C. B., Zard L. Some observations relating to the oximate ion promoted unblocking of oligonucleotide aryl esters. Nucleic Acids Res. 1981 Sep 25;9(18):4611–4626. doi: 10.1093/nar/9.18.4611. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Smith C. C., Aurelian L., Reddy M. P., Miller P. S., Ts'o P. O. Antiviral effect of an oligo(nucleoside methylphosphonate) complementary to the splice junction of herpes simplex virus type 1 immediate early pre-mRNAs 4 and 5. Proc Natl Acad Sci U S A. 1986 May;83(9):2787–2791. doi: 10.1073/pnas.83.9.2787. [DOI] [PMC free article] [PubMed] [Google Scholar]

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