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  • Title: Efforts to expand the genetic alphabet: identification of a replicable unnatural DNA self-pair.
    Author: Henry AA, Olsen AG, Matsuda S, Yu C, Geierstanger BH, Romesberg FE.
    Journal: J Am Chem Soc; 2004 Jun 09; 126(22):6923-31. PubMed ID: 15174862.
    Abstract:
    Six unnatural nucleotides featuring fluorine-substituted phenyl nucleobase analogues have been synthesized, incorporated into DNA, and characterized in terms of the structure and replication properties of the self-pairs they form. Each unnatural self-pair is accommodated in B-form DNA without detectable structural perturbation, and all are thermally stable and selective to roughly the same degree. Furthermore, the efficiency of polymerase-mediated mispair synthesis is similar for each unnatural nucleotide in the template. In contrast, the efficiency of polymerase-mediated self-pair extension is highly dependent on the specific fluorine substitution pattern. The most promising unnatural base pair candidate of this series is the 3-fluorobenzene self-pair, which is replicated with reasonable efficiency and selectivity.
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