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Issue 2, 2019
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2′-Deoxyribonucleoside 5′-triphosphates bearing 4-phenyl and 4-pyrimidinyl imidazoles as DNA polymerase substrates

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Abstract

We developed a versatile access to a series of 4-substituted imidazole 2′-deoxynucleoside triphosphate bearing functionalized phenyl or pyrimidinyl rings. 4-Iodo-1H-imidazole was enzymatically converted into the corresponding 2′-deoxynucleoside, which was then chemically derived into its 5′-triphosphate, followed by 4-arylation via Suzuki–Miyaura coupling using (hetero)arylboronic acids. Both KF (exo-) and Deep Vent (exo-) DNA polymerases incorporated these modified nucleotides in primer-extension assays, adenine being the preferred pairing partner in the template. The 4-(3-aminophenyl)imidazole derivative (3APh) was the most efficiently inserted opposite A by KF (exo-) with only a 37-fold lower efficiency (Vmax/KM) than that of the correct dTTP. No further extension occurred after the incorporation of a single aryl-imidazole nucleotide. Interestingly, the aryl-imidazole dNTPs were found to undergo successive incorporation by calf thymus terminal deoxynucleotidyl transferase with different tailing efficiencies among this series and with a marked preference for 2APyr polymerization.

Graphical abstract: 2′-Deoxyribonucleoside 5′-triphosphates bearing 4-phenyl and 4-pyrimidinyl imidazoles as DNA polymerase substrates

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Publication details

The article was received on 03 Oct 2018, accepted on 04 Dec 2018 and first published on 04 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02464B
Org. Biomol. Chem., 2019,17, 290-301

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    2′-Deoxyribonucleoside 5′-triphosphates bearing 4-phenyl and 4-pyrimidinyl imidazoles as DNA polymerase substrates

    S. Vichier-Guerre, L. Dugué and S. Pochet, Org. Biomol. Chem., 2019, 17, 290
    DOI: 10.1039/C8OB02464B

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