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. 1993 Mar 25;21(6):1473–1479. doi: 10.1093/nar/21.6.1473

Solid-phase synthesis and hybridization properties of DNA containing sulfide-linked dinucleosides.

S H Kawai 1, D Wang 1, P A Giannaris 1, M J Damha 1, G Just 1
PMCID: PMC309335  PMID: 8464740

Abstract

Oligodeoxyribonucleotides incorporating non-hydrolyzable dialkyl sulfide linked thymidine dimers (TsT) were synthesized chemically by the solid-phase approach. The sulfide dimer TsT was stable to degradation by snake-venom phosphodiesterase, calf spleen phosphodiesterase, Nuclease P1 and Nuclease S1. Thermal denaturation analysis indicated that the incorporation of TsT dimers into DNA weakened, but did not prevent, binding to complementary DNA and RNA over a wide range of salt concentrations (10 mM to 2 M NaCl).

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Selected References

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

  1. Augustyns K., Van Aerschot A., Van Schepdael A., Urbanke C., Herdewijn P. Influence of the incorporation of (S)-9-(3,4-dihydroxybutyl)adenine on the enzymatic stability and base-pairing properties of oligodeoxynucleotides. Nucleic Acids Res. 1991 May 25;19(10):2587–2593. doi: 10.1093/nar/19.10.2587. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. 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]
  3. Cormier J. F., Ogilvie K. K. Synthesis of hexanucleotide analogues containing diisopropylsilyl internucleotide linkages. Nucleic Acids Res. 1988 May 25;16(10):4583–4594. doi: 10.1093/nar/16.10.4583. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Dagle J. M., Andracki M. E., DeVine R. J., Walder J. A. Physical properties of oligonucleotides containing phosphoramidate-modified internucleoside linkages. Nucleic Acids Res. 1991 Apr 25;19(8):1805–1810. doi: 10.1093/nar/19.8.1805. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Damha M. J., Giannaris P. A., Zabarylo S. V. An improved procedure for derivatization of controlled-pore glass beads for solid-phase oligonucleotide synthesis. Nucleic Acids Res. 1990 Jul 11;18(13):3813–3821. doi: 10.1093/nar/18.13.3813. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Dolnick B. J. Antisense agents in pharmacology. Biochem Pharmacol. 1990 Aug 15;40(4):671–675. doi: 10.1016/0006-2952(90)90300-a. [DOI] [PubMed] [Google Scholar]
  7. 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]
  8. Froehler B., Ng P., Matteucci M. Phosphoramidate analogues of DNA: synthesis and thermal stability of heteroduplexes. Nucleic Acids Res. 1988 Jun 10;16(11):4831–4839. doi: 10.1093/nar/16.11.4831. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Marcus-Sekura C. J., Woerner A. M., Shinozuka K., Zon G., Quinnan G. V., Jr Comparative inhibition of chloramphenicol acetyltransferase gene expression by antisense oligonucleotide analogues having alkyl phosphotriester, methylphosphonate and phosphorothioate linkages. Nucleic Acids Res. 1987 Jul 24;15(14):5749–5763. doi: 10.1093/nar/15.14.5749. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Matsukura M., Shinozuka K., Zon G., Mitsuya H., Reitz M., Cohen J. S., Broder S. Phosphorothioate analogs of oligodeoxynucleotides: inhibitors of replication and cytopathic effects of human immunodeficiency virus. Proc Natl Acad Sci U S A. 1987 Nov;84(21):7706–7710. doi: 10.1073/pnas.84.21.7706. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Miller P. S., Chandrasegaran S., Dow D. L., Pulford S. M., Kan L. S. Synthesis and template properties of an ethyl phosphotriester modified decadeoxyribonucleotide. Biochemistry. 1982 Oct 26;21(22):5468–5474. doi: 10.1021/bi00265a014. [DOI] [PubMed] [Google Scholar]
  12. Morvan F., Rayner B., Imbach J. L., Thenet S., Bertrand J. R., Paoletti J., Malvy C., Paoletti C. alpha-DNA II. Synthesis of unnatural alpha-anomeric oligodeoxyribonucleotides containing the four usual bases and study of their substrate activities for nucleases. Nucleic Acids Res. 1987 Apr 24;15(8):3421–3437. doi: 10.1093/nar/15.8.3421. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Puglisi J. D., Tinoco I., Jr Absorbance melting curves of RNA. Methods Enzymol. 1989;180:304–325. doi: 10.1016/0076-6879(89)80108-9. [DOI] [PubMed] [Google Scholar]
  14. Stirchak E. P., Summerton J. E., Weller D. D. Uncharged stereoregular nucleic acid analogs: 2. Morpholino nucleoside oligomers with carbamate internucleoside linkages. Nucleic Acids Res. 1989 Aug 11;17(15):6129–6141. doi: 10.1093/nar/17.15.6129. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Thuong N. T., Asseline U., Roig V., Takasugi M., Hélène C. Oligo(alpha-deoxynucleotide)s covalently linked to intercalating agents: differential binding to ribo- and deoxyribopolynucleotides and stability towards nuclease digestion. Proc Natl Acad Sci U S A. 1987 Aug;84(15):5129–5133. doi: 10.1073/pnas.84.15.5129. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Uznanski B., Niewiarowski W., Stec W. J. Activity of acid deoxyribonuclease towards diastereoisomers of thymidyl 3'-(4-nitrophenyl phosphorothioate). Stereochemistry of transnucleotidylation reaction. J Biol Chem. 1986 Jan 15;261(2):592–598. [PubMed] [Google Scholar]
  17. Wilk A., Koziolkiewicz M., Grajkowski A., Uznanski B., Stec W. J. Backbone-modified oligonucleotides containing a butanediol-1,3 moiety as a 'vicarious segment' for the deoxyribosyl moiety--synthesis and enzyme studies. Nucleic Acids Res. 1990 Apr 25;18(8):2065–2068. doi: 10.1093/nar/18.8.2065. [DOI] [PMC free article] [PubMed] [Google Scholar]

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