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Ferrocenylethynyl Derivatives of Nucleoside Triphosphates: Synthesis, Incorporation, Electrochemistry, and Bioanalytical Applications
Author(s) -
Brázdilová Petra,
Vrábel Milan,
Pohl Radek,
Pivoňková Hana,
Havran Luděk,
Hocek Michal,
Fojta Miroslav
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701249
Subject(s) - deoxyribonucleoside , chemistry , combinatorial chemistry , nucleoside , deoxyadenosine , primer (cosmetics) , ferrocene , dna , polymerase , stereochemistry , biochemistry , electrochemistry , organic chemistry , electrode
Abstract Modified dATP (2′‐deoxyadenosine‐5′‐triphosphate) and dUTP (2′‐deoxyuridine‐5′‐triphosphate) bearing ferrocene (Fc) labels linked via a conjugate acetylene spacer were prepared by single‐step aqueous‐phase cross‐coupling reactions of 7‐iodo‐7‐deaza‐dATP or 5‐iodo‐dUTP with ethynylferrocene. The Fc‐labeled dNTPs were good substrates for DNA polymerases and were efficiently incorporated to DNA by primer extension (PEX). Electrochemical analysis of the 2′‐deoxyribonucleoside triphosphates (dNTPs) and PEX products revealed significant differences in redox potentials of the Fc label bound either to U or to 7‐deazaA and between isolated dNTPs and conjugates incorporated to DNA. Prospective bioanalytical applications are outlined.