Synthesis of oligodeoxynucleotides containing N4-mercaptoethylcytosine and their use in the preparation of oligonucleotide-peptide conjugates carrying c-myc tag-sequence

Bioconjugate Chemistry

Volumn 9, Issue 6, 1998, Pages 831-837

  Gottschling, Dirk ^a   Seliger, Hartmut ^b   Tarrasón, Gema ^c   Piulats, Jaume ^c   Eritja, Ramon ^a  

^a EUROPEAN MOLECULAR BIOLOGY LABORATORY   (Germany)

^b UNIVERSITY OF ULM   (Germany)

^c Laboratori de BioInvestigació   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DNA SYNTHESIS; N4 MERCAPTOETHYLCYTOSINE; NUCLEOTIDE SEQUENCE; OLIGODEOXYNUCLEOTIDE;

MONOCLONAL ANTIBODIES; OLIGONUCLEOTIDES;

LABELINGS; LABELLING SYSTEMS; NONRADIOACTIVE; OLIGODEOXYNUCLEOTIDES; OLIGONUCLEOTIDE CONJUGATES; PROPERTY;

PEPTIDES;

EID: 0032213228     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc980074o     Document Type: Article

References (25)

1. Beaucage, S. L., and Iyer, R. P. (1993) The functionalization of oligonucleotides via phosphoramidite derivatives. Tetrahedron 49, 1925-1963.
2. Blanks, R., and McLaughlin, L. W. (1988) An oligodeoxynucleotide affinity column for the isolation of sequence specific DNA binding proteins. Nucleic Acids Res. 16, 10283-10299.
3. Connolly, B. A. (1985) Chemical synthesis of oligonucleotides containing a free sulphydryl group and subsequent attachment of thiol specific probes. Nucleic Acids Res. 13, 4485-4502.
4. Corey D. R. (1995) 48000-fold Acceleration of hybridization by chemically modified oligonucleotides. J. Am. Chem. Soc. 117, 9373-9374.
5. de la Torre, B. G., Aviñó, A., Escarceller, M., Royo, M., Albericio, F., and Eritja, R. (1993) Use of a base-labile protected derivative of 6-mercaptohexanol for the preparation of oligonucleotides containing a thiol group at the 5′-end. Nucleosides Nucleotides 12, 993-1005.
6. Elghanian, R., Storhoff, J. J., Mucic, R. C., Letsinger, R. L., and Mirkin, C. A. (1997) Selective colorimetric detection of poly-nucleotides based on the distance-dependent optical properties of gold nanoparticles. Science 277, 1078-1081.
7. Eritja, R., Pons, A., Escarceller, M., Giralt, E., and Albericio, F. (1991) Synthesis of defined peptide-oligonucleotide hybrids containing a nuclear transport signal sequence. Tetrahedron 47, 4113-4120.
8. Evan, G. I., Lewis, G. K., Ramsay, G., and Bishop, J. M. (1985) Isolation of monoclonal antibodies specific for human c-myc proto-oncogene product. Mol. Cell. Biol. 5, 3610-3616.
9. Fàbrega, C., Eritja, R., Sinha, N. D., Dosanjh, M. K., and Singer, B. (1995) Synthesis and properties of oligonucleotides containing the mutagenic base O4-benzylthymidine. Bioorg. Med. Chem. 3, 101-108.
10. Ferentz, A. E., Keating, T. A., and Verdine, G. L. (1993) Synthesis and characterization of disulfide cross-linked oligonucleotides. J. Am. Chem. Soc. 115, 9006-9014.
11. Fidanza, J. A., and McLaughlin, L. W. (1992) Use of a thiol tether for the site-specific attachment of reporter groups to DNA. J. Org. Chem. 57, 2340-2346.
12. Glick, G. D. (1991) Synthesis of a conformationally restricted DNA hairpin. J. Org. Chem. 56, 6746-6747.
13. Goodwin, J. T., and Glick, G. D. (1993) Incorporation of alkylthiol chains at C-5 of deoxyuridine. Tetrahedron Lett. 34, 5549-5552.
14. Gundlach, C. W., Ryder, T. R., and Glick, G. D. (1997) Synthesis of guanosine analogues bearing pendant alkylthiol tethers. Tetrahedron Lett. 38, 4039-4042.
15. Kuijpers, W. H. A., and van Boeckel, C. A. A. (1993) A new strategy for the solid-phase synthesis of 5′-thiolated oligodeoxynucleotides. Tetrahedron 49, 10931-10944.
16. MacMillan, A. M., and Verdine, G. L. (1991) Engineering tethered DNA molecules by the convertible nucleoside approach. Tetrahedron 47, 2603-2616.
17. Miah, A., Reese, C. B., and Song, Q. (1997) Convenient intermediates for the preparation of C-4 modified derivatives of pyrimidine nucleosides. Nucleosides Nucleotides 16, 53-65.
18. Mirkin, C. A., Letsinger, R. L., Mucic, R. C., and Storhoff, J. J. (1996) A DNA-based method for rational assembling nanoparticles into macroscopic materials. Nature 382, 607-609.
19. Osborne, S. E., Cain, R. J., and Glick, G. D. (1997) Structure and dynamics of disulfide cross-linked DNA triple helixes. J. Am. Chem. Soc. 119, 1171-1182.
20. Rink H. (1987) Solid-phase synthesis of protected peptide fragments using a trialkoxydiphenyl-methylester resin Tetrahedron Lett. 28, 3787.
21. Sarin, U.K., Kent, S. B. H., Tam, J. P., and Merrifield, R. B. (1981) Quantitative Monitoring of solid-phase peptide synthesis by the Ninhydrin reaction. Anal. Biochem 117, 147-157.
22. Sproat, B. S., Beijer, B., Rider, P., and Neuner, P. (1987) The synthesis of protected 5′-mercapto-2′, 5′-dideoxyribonucleoside-3′-O-phosphoramidites; uses of 5′-mercapto-oligodeoxy-nucleotides. Nucleic Acids Res. 15, 4837-4848.
23. Wolfe, S. A., and Verdine, G. L. (1993) Ratcheting torsional stress in duplex DNA. J. Am. Chem. Soc. 115, 12585-12586.
24. Wünsch, E., Moroder, L., and Romani, S. (1982) 1-(tert-Butylthio)-1,2-hydrazinedicarboxylic acid derivatives. Hope-Seyler's Z. Physiol. Chem. 363, 1461-1464.
25. Zuckermann, R. N., and Schultz, P. G. (1988) A hybrid sequence-selective ribonuclease S. J. Am. Chem. Soc. 110, 6592-6594.