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

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• 作者：Pavel Kielkowski^a ; Hana Cahová ; ^a ; Radek Pohl^a ; Michal Hocek^a ; ^b ; ^{hocek@uochb.cas.cz" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Nucleosides ; Nucleotides ; Pyrimidines ; DNA methyltransferases ; DNA polymerases
• 刊名：Bioorganic & Medicinal Chemistry
• 出版年：2016
• 出版时间：15 March 2016
• 年：2016
• 卷：24
• 期：6
• 页码：1268-1276
• 全文大小：1482 K

文摘

New types of double-headed 2′-deoxycytidine 5′-O-triphosphates (dC^XCTPs) 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^XCTPs 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.