Issue 5, 2010
From the journal:

Organic & Biomolecular Chemistry

Synthesis of nucleoside and nucleotide conjugates of bile acids, and polymerase construction of bile acid-functionalized DNA†

Satu Ikonen,ab   Hana Macíčková-Cahová,a   Radek Pohl,a   Miloslav Šandaa  and  Michal Hocek*a  

* Corresponding authors

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead & IOCB Research Center, Flemingovo nam. 2, Prague 6, Czech Republic
E-mail: hocek@uochb.cas.cz
Fax: +420 220183559
Tel: +420 220183324

b Department of Chemistry, University of Jyväskylä, P. O. Box 35, Jyväskylä, Finland

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 acid–nucleoside 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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Article information

DOI
https://doi.org/10.1039/B924072A
Article type
Paper
Submitted
18 Nov 2009
Accepted
04 Dec 2009
First published
15 Jan 2010

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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