Flexible double-headed cytosine-linked 2'-deoxycytidine nucleotides. Synthesis, polymerase incorporation to DNA and interaction with DNA methyltransferases.

Authors :: Kielkowski P
Cahová H
Pohl R
Hocek M
Source :: Bioorganic & medicinal chemistry [Bioorg Med Chem] 2016 Mar 15; Vol. 24 (6), pp. 1268-76. Date of Electronic Publication: 2016 Feb 01.
Publication Year :: 2016
Abstract: New types of double-headed 2'-deoxycytidine 5'-O-triphosphates (dC(XC)TPs) bearing another cytosine or 5-fluorocytosine linked through a flexible propargyl, homopropargyl or pent-1-ynyl linker to position 5 were prepared by the aqueous Sonogashira cross-coupling reactions of 5-iodo-dCTP with the corresponding (fluoro)cytosine-alkynes. The modified dC(XC)TPs were good substrates for DNA polymerases and were used for enzymatic synthesis of cytosine-functionalized DNA by primer extension or PCR. The cytosine- or fluorocytosine-linked DNA probes did not significantly inhibit DNA methyltransferases and did not cross-link to these proteins.<br /> (Copyright © 2016 Elsevier Ltd. All rights reserved.)

Subjects :: Cytosine pharmacology
DNA biosynthesis
DNA (Cytosine-5-)-Methyltransferases antagonists & inhibitors
DNA (Cytosine-5-)-Methyltransferases chemistry
Deoxycytosine Nucleotides chemistry
Deoxycytosine Nucleotides pharmacology
Models, Molecular
Molecular Structure
Cytosine chemistry
Cytosine metabolism
DNA chemistry
DNA metabolism
DNA (Cytosine-5-)-Methyltransferases metabolism
DNA-Directed DNA Polymerase metabolism
Deoxycytosine Nucleotides chemical synthesis
Deoxycytosine Nucleotides metabolism

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