Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 17, Issue 10, Pages 3653-3658Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2009.03.063
Keywords
DNA; Modified nucleotide; DNA polymerase; Fluor; SELEX
Funding
- Konstanz Research School Chemical Biology
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Thymidine analogues 5-trifluoromethyl-, 5-pentafluoroethyl- and 5-(heptafluoro-n-propyl)-2'-deoxyuridines were synthesised and converted into the corresponding 5'-triphosphates 1a-c. Performing DNA polymerase-catalyzed primer extension reactions these modified nucleotides were incorporated into DNA to create perfluoroalkylated nucleic acids. Although single modified nucleotides were enzymatically incorporated and further elongated quite similar to the natural TTP, the enzymatic synthesis of multimodified nucleic acids was initial only feasible with modi. cations at every fourth base. Nevertheless, as the effects of the modified dUTPs on DNA polymerases varied significantly with the used enzyme, Therminator DNA polymerase was proficient in incorporating 11 adjacent 5- trifluoromethyl-2'-deoxyuridine moieties. (C) 2009 Elsevier Ltd. All rights reserved.
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