The incorporation of nucleotides equipped with C-glycosidic aromatic nucleobases into DNA and RNA is an alluring strategy for a number of practical applications including fluorescent labelling of oligonucleotides, expansion of the genetic alphabet for the generation of aptamers and semi-synthetic organisms, or the modulation of excess electron transfer within DNA. However, the generation of C-nucleoside containing oligonucleotides relies mainly on solid-phase synthesis which is quite labor intensive and restricted to short sequences. Here, we explore the possibility of constructing biphenyl-modified DNA sequences using enzymatic synthesis. The presence of multiple biphenyl-units or biphenyl residues modified with electron donors and acceptors permits the incorporation of a single dBphMP nucleotide. Moreover, templates with multiple abasic sites enable the incorporation of up to two dBphMP nucleotides, while TdT-mediated tailing reactions produce single-stranded DNA oligonucleotides with four biphenyl residues appended at the 3'-end.

中文翻译：

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联苯-DNA寡核苷酸的酶促合成。

将具有C-糖苷芳族核碱基的核苷酸掺入DNA和RNA是许多实际应用的诱人策略，包括寡核苷酸的荧光标记，扩展用于产生适体和半合成生物的遗传字母或调节DNA中多余的电子转移。然而，含C-核苷的寡核苷酸的产生主要依赖于固相合成，这是相当费力的并且限于短序列。在这里，我们探索使用酶促合成构建联苯修饰的DNA序列的可能性。被电子供体和受体修饰的多个联苯单元或联苯残基的存在允许掺入单个dBphMP核苷酸。此外，