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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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Supplementary files

Article information


Submitted
18 Nov 2009
Accepted
04 Dec 2009
First published
15 Jan 2010

Org. Biomol. Chem., 2010,8, 1194-1201
Article type
Paper

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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