Skip to main content
NCBI home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1986 Jul 25;14(14):5885–5900. doi: 10.1093/nar/14.14.5885

Use of a 1-hydroxybenzotriazole activated phosphorylating reagent towards the synthesis of short RNA fragments in solution.

E de Vroom, A Fidder, J E Marugg, G A van der Marel, J H van Boom
PMCID: PMC311598  PMID: 2426660

Abstract

Evidence will be presented to show that the reagents 3a-c (X = O) obtained by the reaction of 2-chlorophenylphosphorodichloridate with 1-hydroxybenzotriazole or 1-hydroxy-6-trifluoromethyl (6-nitro) benzotriazoles, respectively, do not give, under normal coupling conditions, phosphorylation of the lactam functions in uracil or guanine. Reagent 3b (X = O) proved to be very convenient for the in situ formation of 3'-5'-phosphotriester linkage. The latter will be illustrated by the synthesis of several RNA fragments.

Full text

PDF
5885

Selected References

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

  1. Efimov V. A., Chakhmakhcheva O. G., Ovchinnikov YuA Improved rapid phosphotriester synthesis of oligodeoxyribonucleotides using oxygen-nucleophilic catalysts. Nucleic Acids Res. 1985 May 24;13(10):3651–3666. doi: 10.1093/nar/13.10.3651. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. 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]
  3. Marugg J. E., Piel N., McLaughlin L. W., Tromp M., Veeneman G. H., van der Marel G. A., van Boom J. H. Polymer supported DNA synthesis using hydroxybenzotriazole activated phosphotriester intermediates. Nucleic Acids Res. 1984 Nov 26;12(22):8639–8651. doi: 10.1093/nar/12.22.8639. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. 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]
  5. 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]
  6. Wreesmann C. T., Fidder A., van der Marel G. A., van Boom J. H. Synthesis of short RNA fragments by the benzotriazolyl phosphotriester approach. Nucleic Acids Res. 1983 Dec 10;11(23):8389–8405. doi: 10.1093/nar/11.23.8389. [DOI] [PMC free article] [PubMed] [Google Scholar]

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

RESOURCES