Skip to main content
NCBI home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1987 Dec 10;15(23):9933–9943. doi: 10.1093/nar/15.23.9933

Preparation of the individual diastereomers of adenylyl-(2'-5')-P-thioadenylyl-(2'-5')-adenosine and their 5'-phosphorylated derivatives.

E de Vroom 1, A Fidder 1, C P Saris 1, G A van der Marel 1, J H van Boom 1
PMCID: PMC306541  PMID: 3697086

Abstract

The individual diastereomers of trimer A2'p5'A2'p(s)5'A, containing one phosphorothioate linkage, were prepared via a modified hydroxybenzotriazole phosphotriester approach. The 5'-phosphorylated derivatives of the latter compounds were obtained after phosphorylation with a 6-trifluoromethyl-1-benzotriazolyl activated phosphoromorpholidate.

Full text

PDF
9933

Selected References

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

  1. Baglioni C., D'Alessandro S. B., Nilsen T. W., den Hartog J. A., Crea R., van Boom J. H. Analogs of (2'-5')oligo(A). Endonuclease activation and inhibition of protein synthesis in intact cells. J Biol Chem. 1981 Apr 10;256(7):3253–3257. [PubMed] [Google Scholar]
  2. Baglioni C., Minks M. A., Maroney P. A. Interferon action may be mediated by activation of a nuclease by pppA2'p5'A2'p5'A. Nature. 1978 Jun 22;273(5664):684–687. doi: 10.1038/273684a0. [DOI] [PubMed] [Google Scholar]
  3. Clemens M. J., Williams B. R. Inhibition of cell-free protein synthesis by pppA2'p5'A2'p5'A: a novel oligonucleotide synthesized by interferon-treated L cell extracts. Cell. 1978 Mar;13(3):565–572. doi: 10.1016/0092-8674(78)90329-x. [DOI] [PubMed] [Google Scholar]
  4. Doetsch P. W., Suhadolnik R. J., Sawada Y., Mosca J. D., Flick M. B., Reichenbach N. L., Dang A. Q., Wu J. M., Charubala R., Pfleiderer W. Core (2'-5')oligoadenylate and the cordycepin analog: inhibitors of Epstein--Barr virus-induced transformation of human lymphocytes in the absence of interferon. Proc Natl Acad Sci U S A. 1981 Nov;78(11):6699–6703. doi: 10.1073/pnas.78.11.6699. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Doetsch P., Wu J. M., Sawada Y., Suhadolnik R. J. Synthesis and characterization of (2'-5')ppp3'dA(p3'dA)n, an analogue of (2'-5')pppA(pA)n. Nature. 1981 May 28;291(5813):355–358. doi: 10.1038/291355a0. [DOI] [PubMed] [Google Scholar]
  6. Eckstein F. Nucleoside phosphorothioates. Annu Rev Biochem. 1985;54:367–402. doi: 10.1146/annurev.bi.54.070185.002055. [DOI] [PubMed] [Google Scholar]
  7. Eppstein D. A., March Y. V., Schryver B. B., Larsen M. A., Barnett J. W., Verheyden J. P., Prisbe E. J. Analogs of (A2'p)nA. Correlation of structure of analogs of ppp(A2'p)2A and (A2'p)2A with stability and biological activity. J Biol Chem. 1982 Nov 25;257(22):13390–13397. [PubMed] [Google Scholar]
  8. Griffin B. E., Jarman M., Reese C. B. The synthesis of oligoribonucleotides. IV. Preparation of dinucleoside phosphates from 2',5'-protected ribonucleoside derivatives. Tetrahedron. 1968 Jan;24(2):639–662. doi: 10.1016/0040-4020(68)88015-9. [DOI] [PubMed] [Google Scholar]
  9. Haugh M. C., Cayley P. J., Serafinowska H. T., Norman D. G., Reese C. B., Kerr I. M. Analogues and analogue inhibitors of ppp(A2'p)nA. Their stability and biological activity. Eur J Biochem. 1983 Apr 15;132(1):77–84. doi: 10.1111/j.1432-1033.1983.tb07327.x. [DOI] [PubMed] [Google Scholar]
  10. Hughes B. G., Srivastava P. C., Muse D. D., Robins R. K. 2',5'-Oligoadenylates and related 2',5'-oligonucleotide analogues. 1. Substrate specificity of the interferon-induced murine 2',5'-oligoadenylate synthetase and enzymatic synthesis of oligomers. Biochemistry. 1983 Apr 26;22(9):2116–2126. doi: 10.1021/bi00278a011. [DOI] [PubMed] [Google Scholar]
  11. Imai J., Johnston M. I., Torrence P. F. Chemical modification potentiates the biological activities of 2-5A and its congeners. J Biol Chem. 1982 Nov 10;257(21):12739–12745. [PubMed] [Google Scholar]
  12. Jamoulle J. C., Imai J., Lesiak K., Torrence P. F. Synthesis and biological activity of tubercidin analogues of ppp5'A2'p(5'A2'p)n5'A. Biochemistry. 1984 Jun 19;23(13):3063–3069. doi: 10.1021/bi00308a033. [DOI] [PubMed] [Google Scholar]
  13. Jamoulle J. C., Imai J., Lesiak K., Torrence P. F. Synthesis and biological activity of tubercidin analogues of ppp5'A2'p(5'A2'p)n5'A. Biochemistry. 1984 Jun 19;23(13):3063–3069. doi: 10.1021/bi00308a033. [DOI] [PubMed] [Google Scholar]
  14. Kerr I. M., Brown R. E. pppA2'p5'A2'p5'A: an inhibitor of protein synthesis synthesized with an enzyme fraction from interferon-treated cells. Proc Natl Acad Sci U S A. 1978 Jan;75(1):256–260. doi: 10.1073/pnas.75.1.256. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Krause D., Lesiak K., Imai J., Sawai H., Torrence P. F., Silverman R. H. Activation of 2-5A-dependent RNase by analogs of 2-5A (5'-O-triphosphoryladenylyl(2'----5')adenylyl(2'----5')adenosine ) using 2',5'-tetraadenylate (core)-cellulose. J Biol Chem. 1986 May 25;261(15):6836–6839. [PubMed] [Google Scholar]
  16. 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]
  17. Lesiak K., Torrence P. F. Synthesis and biological activity of a fluorescent analogue of 2-5A. FEBS Lett. 1983 Jan 24;151(2):291–296. doi: 10.1016/0014-5793(83)80089-1. [DOI] [PubMed] [Google Scholar]
  18. Markham A. F., Porter R. A., Gait M. J., Sheppard R. C., Kerr I. M. Rapid chemical synthesis and circular dichroism properties of some 2'-5'-linked oligoriboadenylates. Nucleic Acids Res. 1979 Jun 11;6(7):2569–2582. doi: 10.1093/nar/6.7.2569. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Nyilas A., Vrang L., Drake A., Oberg B., Chattopadhyaya J. The cordycepin analogue of 2,5A and its threo isomer. Chemical synthesis, conformation and biological activity. Acta Chem Scand B. 1986 Sep;40(8):678–688. doi: 10.3891/acta.chem.scand.40b-0678. [DOI] [PubMed] [Google Scholar]
  20. 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]
  21. Sawai H., Imai J., Lesiak K., Johnston M. I., Torrence P. F. Cordycepin analogues of 2-5A and its derivatives. Chemical synthesis and biological activity. J Biol Chem. 1983 Feb 10;258(3):1671–1677. [PubMed] [Google Scholar]
  22. Sawai H., Lesiak K., Imai J., Torrence P. F. Replacement of the ribofuranose oxygen of 2-5A derivatives by methylene: synthesis of an aristeromycin analogue of 2-5A core 5'-monophosphate (5'-O-phosphoryladenylyl)(2'----5')adenyl(2'----5')adenosine. J Med Chem. 1985 Sep;28(9):1376–1380. doi: 10.1021/jm00147a048. [DOI] [PubMed] [Google Scholar]
  23. Schattenkerk C., Wreesmann C. T., van der Marel G. A., van Boom J. H. Synthesis of riboguanosine pentaphosphate ppprGpp (Magic Spot II) via a phosphotriester approach. Nucleic Acids Res. 1985 May 24;13(10):3635–3649. doi: 10.1093/nar/13.10.3635. [DOI] [PMC free article] [PubMed] [Google Scholar]
  24. Schmidt A., Chernajovsky Y., Shulman L., Federman P., Berissi H., Revel M. An interferon-induced phosphodiesterase degrading (2'-5') oligoisoadenylate and the C-C-A terminus of tRNA. Proc Natl Acad Sci U S A. 1979 Oct;76(10):4788–4792. doi: 10.1073/pnas.76.10.4788. [DOI] [PMC free article] [PubMed] [Google Scholar]
  25. Stawinski J., Hozumi T., Narang S. A., Bahl C. P., Wu R. Arylsulfonyltetrazoles, new coupling reagents and further improvements in the triester method for the synthesis of deoxyribooligonucleotides. Nucleic Acids Res. 1977 Feb;4(2):353–371. doi: 10.1093/nar/4.2.353. [DOI] [PMC free article] [PubMed] [Google Scholar]
  26. Torrence P. F., Imai J., Lesiak K., Jamoulle J. C., Sawai H. Oligonucleotide structural parameters that influence binding of 5'-O-triphosphoadenylyl-(2'----5')-adenylyl-(2'----5')-adenosine to the 5'-O-triphosphoadenylyl-(2'----5')-adenylyl-(2'----5')-adenosine dependent endoribonuclease: chain length, phosphorylation state, and heterocyclic base. J Med Chem. 1984 Jun;27(6):726–733. doi: 10.1021/jm00372a004. [DOI] [PubMed] [Google Scholar]
  27. de Vroom E., Fidder A., Marugg J. E., van der Marel G. A., van Boom J. H. Use of a 1-hydroxybenzotriazole activated phosphorylating reagent towards the synthesis of short RNA fragments in solution. Nucleic Acids Res. 1986 Jul 25;14(14):5885–5900. doi: 10.1093/nar/14.14.5885. [DOI] [PMC free article] [PubMed] [Google Scholar]
  28. van der Marel G. A., van Boeckel C. A., Wille G., van Boom J. H. A general method for the synthesis of 5'-monophosphates of DNA fragments via phosphotriester intermediates. Nucleic Acids Res. 1982 Apr 10;10(7):2337–2351. doi: 10.1093/nar/10.7.2337. [DOI] [PMC free article] [PubMed] [Google Scholar]

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

RESOURCES