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2-Trifluoromethyl-6-mercurianiline Nucleotide, a Sensitive F-19 NMR Probe for Hg(II)-mediated Base Pairing




TekijätAro-Heinilä Asmo, Lepistö Assi, Äärelä Antti, Lönnberg Tuomas Antti, Virta Pasi

KustantajaAMER CHEMICAL SOC

Julkaisuvuosi2022

JournalJournal of Organic Chemistry

Tietokannassa oleva lehden nimiJOURNAL OF ORGANIC CHEMISTRY

Lehden akronyymiJ ORG CHEM

Vuosikerta87

Numero1

Aloitussivu137

Lopetussivu146

Sivujen määrä10

ISSN0022-3263

eISSN1520-6904

DOIhttps://doi.org/10.1021/acs.joc.1c02056

Verkko-osoitehttps://pubs.acs.org/doi/10.1021/acs.joc.1c02056

Rinnakkaistallenteen osoitehttps://research.utu.fi/converis/portal/detail/Publication/174963139


Tiivistelmä
A 2-trifluoromethylaniline C-nucleoside was synthesized, incorporated in the middle of an oligonucleotide, and mercurated. The affinity of the mercurated oligonucleotide toward complementary strands placing each of the canonical nucleobases opposite to the organomercury nucleobase analogue was examined by ultraviolet (UV), circular dichroism (CD), and F-19 NMR spectroscopy analyses. According to the UV melting profile analysis, the organomercury nucleobase analogue showed increased affinities in the order T > G > C > A. The CD profiles indicated the typical B-type helix in each case. The F-19 resonance signal proved sensitive for the local environmental changes, showing clearly distinct signals for the duplexes with different opposing nucleobases. Furthermore, valuable information on the mercurated oligonucleotide and its binding to complementary strands at varying temperature could be obtained by F-19 NMR spectroscopy.

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