Ferrocenylethynyl derivatives of nucleoside triphosphates: synthesis, incorporation, electrochemistry, and bioanalytical applications.
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.
Brázdilová
Petra
P
Institute of Biophysics, v.v.i. Academy of Sciences of the Czech Republic, Kralovopolska 135, 61265 Brno, Czech Republic.
Vrábel
Milan
M
Pohl
Radek
R
Pivonková
Hana
H
Havran
Ludek
L
Hocek
Michal
M
Fojta
Miroslav
M
D004563:Electrochemistry; D005296:Ferrous Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009711:Nucleotides / Q000032:analysis* / Q000138:chemical synthesis* / Q000737:chemistry / Q000235:genetics; D010710:Phosphates / Q000737:chemistry*
D005296:Ferrous Compounds; D009711:Nucleotides; D010710:Phosphates