Synthesis of functionalized biphenyl-C-nucleosides and their incorporation into oligodeoxynucleotides.

Synthesis of functionalized biphenyl-C-nucleosides and their incorporation into oligodeoxynucleotides.
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功能化联苯-C-核苷的合成及其掺入寡脱氧核苷酸。

DOI:
10.1016/j.bmc.2006.05.072
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发表时间:
2006
影响因子:
3.5
通讯作者:
C. Leumann
C. Leumann
中科院分区:
医学3区
文献类型:
--
作者:
A. Zahn;C. Leumann

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We describe the synthesis of eight novel C-nucleosides in which the nucleobases are replaced by biphenyl residues that carry one or two electron donor (–OCH3,–NH2) or acceptor (–NO2) functional groups in the distal ring. These C-nucleosides were synthesized convergently and in high yields from a common bromophenyl-C-nucleoside precursor via Suzuki coupling with the respective boronic acids or esters. These nucleosides were subsequently converted into the corresponding phosphoramidite building blocks and efficiently incorporated into oligodeoxynucleotides by standard phosphoramidite chemistry.
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