Skip to main content
NCBI home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1995 Jan 11;23(1):51–57. doi: 10.1093/nar/23.1.51

Incorporation of 2'-amido-nucleosides in oligodeoxynucleotides and oligoribonucleotides as a model for 2'-linked conjugates.

C Hendrix 1, B Devreese 1, J Rozenski 1, A van Aerschot 1, A De Bruyn 1, J Van Beeumen 1, P Herdewijn 1
PMCID: PMC306629  PMID: 7870590

Abstract

The functionalisation of oligodeoxynucleotides and oligoribonucleotides by incorporation of 2'-amido-2'-deoxyribonucleosides, possibly containing a reporter group via the 2'-amido bond, was examined. Therefore 2'-acetamido-ribonucleosides containing a small methyl group at the 2'-amido bond were synthesized as model compounds. In order to evaluate the influence of this 2'-modification on the hybridization capacities, 2'-acetamido-2'-deoxyuridine was incorporated in both RNA and DNA strands. The suitability of phosphoramidite chemistry for the introduction of this modified nucleoside was proven using laser desorption mass spectrometry of the final oligonucleotide. The presence of the 2'-modification destabilised both RNA-RNA, DNA-DNA and mixed duplexes. Therefore, it can be concluded that the 2'-acetamido group is not a good linker for attachment of reporter groups to oligonucleotides.

Full text

PDF
51

Selected References

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

  1. Augustyns K., Godard G., Hendrix C., Van Aerschot A., Rozenski J., Saison-Behmoaras T., Herdewijn P. Hybridization specificity, enzymatic activity and biological (Ha-ras) activity of oligonucleotides containing 2,4-dideoxy-beta-D-erythro-hexopyranosyl nucleosides. Nucleic Acids Res. 1993 Oct 11;21(20):4670–4676. doi: 10.1093/nar/21.20.4670. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Augustyns K., Vandendriessche F., Van Aerschot A., Busson R., Urbanke C., Herdewijn P. Incorporation of hexose nucleoside analogues into oligonucleotides: synthesis, base-pairing properties and enzymatic stability. Nucleic Acids Res. 1992 Sep 25;20(18):4711–4716. doi: 10.1093/nar/20.18.4711. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Aurup H., Tuschl T., Benseler F., Ludwig J., Eckstein F. Oligonucleotide duplexes containing 2'-amino-2'-deoxycytidines: thermal stability and chemical reactivity. Nucleic Acids Res. 1994 Jan 11;22(1):20–24. doi: 10.1093/nar/22.1.20. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Covey T. R., Huang E. C., Henion J. D. Structural characterization of protein tryptic peptides via liquid chromatography/mass spectrometry and collision-induced dissociation of their doubly charged molecular ions. Anal Chem. 1991 Jul 1;63(13):1193–1200. doi: 10.1021/ac00013a003. [DOI] [PubMed] [Google Scholar]
  5. Furukawa Y., Honjo M. A novel method for the synthesis of purine nucleosides using Friedel-Crafts catalysts. Chem Pharm Bull (Tokyo) 1968 Jun;16(6):1076–1080. doi: 10.1248/cpb.16.1076. [DOI] [PubMed] [Google Scholar]
  6. Ono A., Chen C. N., Kan L. S. DNA triplex formation of oligonucleotide analogues consisting of linker groups and octamer segments that have opposite sugar-phosphate backbone polarities. Biochemistry. 1991 Oct 15;30(41):9914–9912. doi: 10.1021/bi00105a015. [DOI] [PubMed] [Google Scholar]
  7. Pieles U., Zürcher W., Schär M., Moser H. E. Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: a powerful tool for the mass and sequence analysis of natural and modified oligonucleotides. Nucleic Acids Res. 1993 Jul 11;21(14):3191–3196. doi: 10.1093/nar/21.14.3191. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Temsamani J., Tang J. Y., Padmapriya A., Kubert M., Agrawal S. Pharmacokinetics, biodistribution, and stability of capped oligodeoxynucleotide phosphorothioates in mice. Antisense Res Dev. 1993 Fall;3(3):277–284. doi: 10.1089/ard.1993.3.277. [DOI] [PubMed] [Google Scholar]
  9. Van Aerschot A., Everaert D., Balzarini J., Augustyns K., Jie L., Janssen G., Peeters O., Blaton N., De Ranter C., De Clercq E. Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides. J Med Chem. 1990 Jun;33(6):1833–1839. doi: 10.1021/jm00168a046. [DOI] [PubMed] [Google Scholar]
  10. Verheyden J. P., Wagner D., Moffatt J. G. Synthesis of some pyrimidine 2'-amino-2'-deoxynucleosides. J Org Chem. 1971 Jan 29;36(2):250–254. doi: 10.1021/jo00801a002. [DOI] [PubMed] [Google Scholar]
  11. Wagner R. W., Matteucci M. D., Lewis J. G., Gutierrez A. J., Moulds C., Froehler B. C. Antisense gene inhibition by oligonucleotides containing C-5 propyne pyrimidines. Science. 1993 Jun 4;260(5113):1510–1513. doi: 10.1126/science.7684856. [DOI] [PubMed] [Google Scholar]

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

RESOURCES