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Issue 31, 2013
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Deoxynucleoside triphosphates bearing histamine, carboxylic acid, and hydroxyl residues – synthesis and biochemical characterization

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Abstract

Modified nucleoside triphosphates (dAHsTP, dUPOHTP, and dCValTP) bearing imidazole, hydroxyl, and carboxylic acid residues connected to the purine and pyrimidine bases through alkyne linkers were prepared. These modified dN*TPs were excellent substrates for various DNA polymerases in primer extension reactions. Moreover, the combined use of terminal deoxynucleotidyl transferase (TdT) and the modified dNTPs led to efficient tailing reactions that rival those of natural counterparts. Finally, the triphosphates were tolerated by polymerases under PCR conditions, and the ensuing modified oligonucleotides served as templates for the regeneration of unmodified DNA. Thus, these modified dN*TPs are fully compatible with in vitro selection methods and can be used to develop artificial peptidases based on DNA.

Graphical abstract: Deoxynucleoside triphosphates bearing histamine, carboxylic acid, and hydroxyl residues – synthesis and biochemical characterization

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Publication details

The article was received on 24 Apr 2013, accepted on 05 Jun 2013 and first published on 06 Jun 2013


Article type: Paper
DOI: 10.1039/C3OB40842F
Org. Biomol. Chem., 2013,11, 5162-5172
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    Deoxynucleoside triphosphates bearing histamine, carboxylic acid, and hydroxyl residues – synthesis and biochemical characterization

    M. Hollenstein, Org. Biomol. Chem., 2013, 11, 5162
    DOI: 10.1039/C3OB40842F

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