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Journal Articles Bioorganic and Medicinal Chemistry Year : 2020

Enzymatic synthesis of biphenyl-DNA oligonucleotides

Abstract

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.
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pasteur-02625707 , version 1 (06-07-2020)

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Pascal Röthlisberger, Fabienne Levi-Acobas, Christian Leumann, Marcel Hollenstein. Enzymatic synthesis of biphenyl-DNA oligonucleotides. Bioorganic and Medicinal Chemistry, 2020, 28 (11), pp.115487. ⟨10.1016/j.bmc.2020.115487⟩. ⟨pasteur-02625707⟩
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