Skip to main content
PMC home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1975 May;2(5):699–706. doi: 10.1093/nar/2.5.699

Synthetic analogues of polynucleotides. (Part) XIV. The synthesis of poly (3'-0-carboxymethyl-2'-deoxycytidine) and its interaction with polyinosinic acid.

R C Bleaney, A S Jones, R T Walker
PMCID: PMC343622  PMID: 1144061

Abstract

Poly (3'-O-carboxymethyl-2'-deoxyctidine) (VII) has been synthesised by the polymerisation of 3'-O-carboxymethyl-4-N-phenoxyacety-2'-deoxycytidine (V) and removal of the phenoxyacetyl groups under acidic conditions. V was obtained by the action of 2,4-dinitrophenyl phenylacetate on 3'-O-carboxymethyl-5'-O-triphenylmethyl-2'-deoxycytidine (III) followed by removal of the triphenylmethyl group under carefully controlled acidic conditions. The polymer, VII gave a hypochromic effect of about 20% at 250nm when mixed with poly (1) in 0.2Macetate, pH 5.0. It appeared, therefore, that a complex was formed. Upon heating a solution of this complex there was an initial decrease in optical density followed by a much larger increase to give a Tm of about 60 degrees. Attempts to form the 3'-O-carboxymethyl derivative of 4-N-phenoxyacetyl-5'-O-'triphenylmethyl-2'-deoxycytidine to give a shorter synthetic route to VII were not successful. 3'-O-Carboxymethyl-2'-deoxycytidine was obtained by removal of thetriphenylmethyl group from III. Attempts to polymerise this compound in concentrated aqueous solution with a water-soluble carbodiimide were not successful.

Full text

PDF
706

Selected References

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

  1. Cowling G. J., Jones A. S., Walker R. T. Polynucleotide analogue inhibition of messenger-stimulated transfer RNA binding to ribosomes. Biochim Biophys Acta. 1971 Dec 30;254(3):452–456. doi: 10.1016/0005-2787(71)90879-3. [DOI] [PubMed] [Google Scholar]
  2. Edge M. D., Hodgson A., Jones A. S., MacCoss M., Walker R. T. Synthetic analogues of polynucleotides. IX. Synthesis of 3'-O-carboxymethyl-2'-deoxyribonucleosides and their use in the synthesis of an analogue of 2'-deoxyadenylyl-(3' leads to 5'-)-thymidine 3'-phosphate. J Chem Soc Perkin 1. 1973;3:290–294. [PubMed] [Google Scholar]
  3. Edge M. D., Hodgson A., Jones A. S., Walker R. T. Synthetic analogues of polynucleotides. 8. Analogues of oligonucleotides containing carboxymethylthymidine. J Chem Soc Perkin 1. 1972;16:1991–1996. doi: 10.1039/p19720001991. [DOI] [PubMed] [Google Scholar]
  4. Edge M. D., Jones A. S. Synthetic analogues of polynucleotides. V. Analogues of trinucleoside diphosphates containing carboxymethylthymidine. J Chem Soc Perkin 1. 1971;10:1933–1939. doi: 10.1039/j39710001933. [DOI] [PubMed] [Google Scholar]
  5. Gait M. J., Jones A. S., Walker R. T. Synthetic-analogues of polynucleotides XII. Synthesis of thymidine derivatives containing an oxyacetamido- or an oxyformamido-linkage instead of a phosphodiester group. J Chem Soc Perkin 1. 1974;0(14):1684–1686. [PubMed] [Google Scholar]
  6. Halford M. H., Jones A. S. Synthetic analogues of polynucleotides. IV. Carboxymethyl derivatives of uridine and of thymidine. J Chem Soc Perkin 1. 1968;21:2667–2670. doi: 10.1039/j39680002667. [DOI] [PubMed] [Google Scholar]
  7. Jones A. S., MacCoss M., Walker R. T. Synthetic analogues of polynucleotides. X. The synthesis of poly-(3'-O-carboxymethyl-2'-deoxyadenosine) and its interaction with polynucleotides. Biochim Biophys Acta. 1973 Feb 4;294(1):365–377. [PubMed] [Google Scholar]
  8. Steward D. L., Herndon W. C., Jr, Schell K. R. Influence of 2'-O-acetylation on the antiviral activity of polyribonucleotides. Biochim Biophys Acta. 1972 Mar 14;262(2):227–232. doi: 10.1016/0005-2787(72)90237-7. [DOI] [PubMed] [Google Scholar]

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

RESOURCES