Abstract
The syntheses of 5-arylsulfanyl- or 5-arylselanylpyrimidine and 7-arylsulfanyl- or 7-arylselanyl-7-deazapurine nucleosides and nucleotides were developed by the Cu-mediated sulfanylations or selanylations of the corresponding 5-iodopyrimidine or 7-iodo-7-deazapurine nucleosides or nucleotides with diaryldisulfides or -diselenides. The reactions were also applicable for direct modifications of 2'-deoxycytidine triphosphate and the resulting 5-arylsulfanyl or 5-arylselanyl-dCTP served as substrates for the polymerase synthesis of modified DNA bearing arylsulfanyl or arylselanyl groups in the major groove.
Highlights
DNA molecules bearing modifications in the major groove have found diverse applications mainly in bioanalysis and chemical biology.1 5-Substituted pyrimidine and 7-substituted 7-deazapurine 2′-deoxyribonucleoside 5′-O-triphosphates (dNTPs) are good substrates for DNA polymerases in the enzymatic synthesis of base-modified DNA.[2,3] Modified dNTPs are mostly synthesized by the triphosphorylation of the corresponding modified nucleosides[4] but this approach can fail in the case of some reactive modifications not compatible with the triphosphorylation methodology
Modified deoxyribonucleoside 5′-O-triphosphates (dNTPs) are mostly synthesized by the triphosphorylation of the corresponding modified nucleosides[4] but this approach can fail in the case of some reactive modifications not compatible with the triphosphorylation methodology
We developed a new method for the direct functionalization of 5-iodopyrimidine and 7-iodo-7-deazapurine nucleosides and nucleotides based on Cu-mediated arylsulfanylation or aryl/alkylselenylation
Summary
DNA molecules bearing modifications in the major groove have found diverse applications mainly in bioanalysis and chemical biology.1 5-Substituted pyrimidine and 7-substituted 7-deazapurine 2′-deoxyribonucleoside 5′-O-triphosphates (dNTPs) are good substrates for DNA polymerases in the enzymatic synthesis of base-modified DNA.[2,3] Modified dNTPs are mostly synthesized by the triphosphorylation of the corresponding modified nucleosides[4] but this approach can fail in the case of some reactive modifications not compatible with the triphosphorylation methodology. The reactions were applicable for direct modifications of 2’-deoxycytidine triphosphate and the resulting 5-arylsulfanyl or 5-arylselanyl-dCTP served as substrates for the polymerase synthesis of modified DNA bearing arylsulfanyl or arylselanyl groups in the major groove. We report here the synthesis of the arylsulfanyl and arylselanyl derivatives of pyrimidine and 7-deazapurine nucleosides and nucleotides and their potential for polymerase incorporation into DNA.
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