Post-synthetic introduction of labile functionalities onto purine residues via 6-methylthiopurines in oligodeoxyribonucleotides
Two methods are described for the preparation of oligodeoxynucleotides containing 6-methylthiopurine residues. 6-Methylthiopurine phosphoramidite (6) has been prepared and incorporated into oligomers. Methylation with methyl iodide of 6-thiopurine (or 6-thioguanine) in oligomers also exclusively produces oligomers containing 6-methylthiopurine (or 6-methylthioguanine). The methylthio group at defined purine residues in the deprotected oligomers can be oxidized selectively and converted at the final step into various functional groups including radioactive 35S-thio group, a useful tag for cross-linking studies.
SYNTHESIS AND CROSSLINKING PROPERTIES OF A DEOXYOLIGONUCLEOTIDE CONTAINING N6,N6-ETHANODEOXYADENOSINE
We report the synthesis of 5' HO-dT6(N6,N6-ethanodeoxyadenosine)T14.This oligonucleotide specifically crosslinks with 5' HO-dA14CA6T at pH 7.5 and 20 deg C with a half-life of approximately one day.
Preparation of oligodeoxynucleotides containing 6-methylthiopurine residues by chemical synthesis or specific methylation
Two methods (chemical synthesis and specific methylation) are described for the preparation of oligodeoxynucleotides containing 6-methylthiopurine residues. 6-Methylthiopurine phosphoramidite (6) is prepared and incorporated into oligomers. Methylation with methyl iodide of 6-thiopurine (or 6-thioguanine) in oligonucleotides also leads to exclusive production of 6-methylthiopurine (or 6-methylthioguanine) oligomers.
Xu,Zheng,Swann
p. 929 - 933
(2007/10/02)
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