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. 2010 Aug 18;15(8):5692-707.
doi: 10.3390/molecules15085692.

Solid-phase synthesis of oligodeoxynucleotides containing N4-[2-(t-butyldisulfanyl)ethyl]-5-methylcytosine moieties

Sónia Pérez-Rentero  1 , Alejandra V Garibotti, Ramón Eritja
Affiliations

Solid-phase synthesis of oligodeoxynucleotides containing N4-[2-(t-butyldisulfanyl)ethyl]-5-methylcytosine moieties

Sónia Pérez-Rentero et al. Molecules. .

Abstract

An efficient route for the synthesis of the phosphoramidite derivative of 5-methylcytosine bearing a tert-butylsulfanyl group protected thiol is described. This building block is used for the preparation of oligonucleotides carrying a thiol group at the nucleobase at the internal position of a DNA sequence. The resulting thiolated oligonucleotides are useful intermediates to generate oligonucleotide conjugates carrying molecules of interest at internal positions of a DNA sequence.

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Figures

Scheme 1
Scheme 1
Synthesis of the protected phosphoramidite derivative of 2’-deoxy-[2-(t-butyldisulfanyl)ethyl]-5-methylcytidine.
Scheme 2
Scheme 2
Products obtained after treatment of DMT-MeC(SStBu)-CPG (5) and DMT-C(SStBu)-CPG (6) with iodine or tert-butylhydroperoxide solutions. Reagents and conditions: (a) iodine or tert-butylhydroperoxide solution. (b) 3% trichloroacetic acid in dichloromethane. (c) concentrated ammonia, room temperature, 30 min.
Scheme 3
Scheme 3
Products obtained after treatment of DMT-CBzpMeC(SStBu)-CPG (11) and DMT-CBzpC(SStBu)-CPG (12) with iodine solution.
Scheme 4
Scheme 4
Potential products produced during the synthesis of oligonucleotides carrying N4- [2-(t-butyldisulfanyl)ethyl]-5-methylcytosine.
Figure 1
Figure 1
HPLC profiles of oligonucleotide 5’-d(TTCCAXATTACCG)-3’ after synthesis and after prolonged treatment of the support with tert-butylhydroperoxide solution for 6 and 12 h.
Scheme 5
Scheme 5
Synthesis of oligonucleotides carrying fluorescent molecules.
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References

    1. Beaucage S.L., Iyer R.P. The functionalization of oligonucleotide via phosphoramidite derivatives. Tetrahedron. 1993;49:1925–1963. doi: 10.1016/S0040-4020(01)86295-5. - DOI
    1. Connolly B.A. Chemical synthesis of oligonucleotides containing a free sulphydryl group and subsequent attachment of thiol specific probes. Nucleic Acids Res. 1985;13:4485–4502. doi: 10.1093/nar/13.12.4485. - DOI - PMC - PubMed
    1. Corey D.R. 48000-fold Acceleration of hybridization by chemically modified oligonucleotides. J. Am. Chem. Soc. 1995;117:9373–9374. doi: 10.1021/ja00141a038. - DOI
    1. Eritja R., Pons A., Escarceller M., Giralt E., Albericio F. Synthesis of defined peptide-oligonucleotide hybrids containing a nuclear transport signal sequence. Tetrahedron. 1991;47:4113–4120. doi: 10.1016/S0040-4020(01)86448-6. - DOI
    1. Zuckermann R.N., Schultz P.G. A hybrid sequence selective ribonuclease S. J. Am. Chem. Soc. 1988;110:6592–6594. doi: 10.1021/ja00227a066. - DOI

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