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@article{1621399,
author = {HavranovaandVidlakova, P. and Kromer, M. and Sykorova, V. and Trefulka, M. and Fojta, Miroslav and Havran, L. and Hocek, M.},
article_location = {WEINHEIM},
article_number = {1-2},
doi = {http://dx.doi.org/10.1002/cbic.201900388},
keywords = {DNA; electrochemistry; nucleotides; osmium; redox labeling},
language = {eng},
issn = {1439-4227},
journal = {Chembiochem},
title = {Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cbic.201900388},
volume = {21},
year = {2020}
}
TY - JOUR
ID - 1621399
AU - Havranova-Vidlakova, P. - Kromer, M. - Sykorova, V. - Trefulka, M. - Fojta, Miroslav - Havran, L. - Hocek, M.
PY - 2020
TI - Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes
JF - Chembiochem
VL - 21
IS - 1-2
SP - 171-180
EP - 171-180
PB - WILEY-VCH
SN - 14394227
KW - DNA
KW - electrochemistry
KW - nucleotides
KW - osmium
KW - redox labeling
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cbic.201900388
N2 - Six-valent osmium (osmate) complexes with nitrogenous ligands have previously been used for the modification and redox labeling of biomolecules involving vicinal diol moieties (typically, saccharides or RNA). In this work, aliphatic (3,4-dihydroxybutyl and 3,4-dihydroxybut-1-ynyl) or cyclic (6-oxo-6-(cis-3,4-dihydroxypyrrolidin-1-yl)hex-2-yn-1-yl, PDI) vicinal diols are attached to nucleobases to functionalize DNA for subsequent redox labeling with osmium(VI) complexes. The diol-linked 2 '-deoxyribonucleoside triphosphates were used for the polymerase synthesis of diol-linked DNA, which, upon treatment with K2OsO3 and bidentate nitrogen ligands, gave the desired Os-labeled DNA, which were characterized by means of the gel-shift assay and ESI-MS. Through ex situ square-wave voltammetry at a basal plane pyrolytic graphite electrode, the efficiency of modification/labeling of individual diols was evaluated. The results show that the cyclic cis-diol (PDI) was a better target for osmylation than that of the flexible aliphatic ones (alkyl- or alkynyl-linked). The osmate adduct-specific voltammetric signal obtained for Os-VI-treated DNA decorated with PDI showed good proportionality to the number of PDI per DNA molecule. The Os-VI reagents (unlike OsO4) do not attack nucleobases; thus offering specificity of modification on the introduced glycol targets.
ER -
HAVRANOVA-VIDLAKOVA, P., M. KROMER, V. SYKOROVA, M. TREFULKA, Miroslav FOJTA, L. HAVRAN a M. HOCEK. Vicinal Diol-Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes. \textit{Chembiochem}. WEINHEIM: WILEY-VCH, 2020, roč.~21, 1-2, s.~171-180. ISSN~1439-4227. Dostupné z: https://dx.doi.org/10.1002/cbic.201900388.
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