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Issue 5, 2010
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Synthesis of nucleoside and nucleotide conjugates of bile acids, and polymerase construction of bile acid-functionalized DNA

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Abstract

Aqueous Sonogashira cross-coupling reactions of 5-iodopyrimidine or 7-iodo-7-deazaadenine nucleosides with bile acid-derived terminal acetylenes linked via an ester or amide tether gave the corresponding bile acidnucleoside conjugates. Analogous reactions of halogenated nucleoside triphosphates gave directly bile acid-modified dNTPs. Enzymatic incorporation of these modified nucleotides to DNA was successfully performed using Phusion polymerase for primer extension. One of the dNTPs (dCTP bearing cholic acid) was also efficient for PCR amplification.

Graphical abstract: Synthesis of nucleoside and nucleotide conjugates of bile acids, and polymerase construction of bile acid-functionalized DNA

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Publication details

The article was received on 18 Nov 2009, accepted on 04 Dec 2009 and first published on 15 Jan 2010


Article type: Paper
DOI: 10.1039/B924072A
Citation: Org. Biomol. Chem., 2010,8, 1194-1201
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    Synthesis of nucleoside and nucleotide conjugates of bile acids, and polymerase construction of bile acid-functionalized DNA

    S. Ikonen, H. Macíčková-Cahová, R. Pohl, M. Šanda and M. Hocek, Org. Biomol. Chem., 2010, 8, 1194
    DOI: 10.1039/B924072A

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