Electron Injection into DNA: Synthesis and Spectroscopic Properties of Pyrenyl-modified Oligonucleotides
Affiliations
The nucleoside 5-(1-pyrenyl)-2'-deoxyuridine (1) was prepared by a Suzuki-Miyaura cross-coupling reaction and subsequently used as a DNA building block in order to prepare a range of modified oligonucleotides using phosphoramidite chemistry. The DNA duplexes contain a pyrenyl group covalently attached to the nucleobase uracil. Upon excitation at 340 nm an intramolecular electron transfer from the pyrenyl group to the uracil moiety takes place which represents an injection of an excess electron into the DNA base stack. Based on the results obtained by steady-state fluorescence and time-resolved pump-probe laser spectroscopy it was possible to show that base-to-base electron transfer can occur from the Py-dU group only to adjacent thymines.
Reductive Photocycloreversion of Cyclobutane Dimers Triggered by Guanines.
Rodriguez-Muniz G, Fraga-Timiraos A, Navarrete-Miguel M, Borrego-Sanchez A, Roca-Sanjuan D, Miranda M J Org Chem. 2023; 88(14):10111-10121.
PMID: 37437138 PMC: 10367068. DOI: 10.1021/acs.joc.3c00930.
Detection of cofilin mRNA by hybridization-sensitive double-stranded fluorescent probes.
Lee H, Go G, Ro J, Kim B RSC Adv. 2022; 8(14):7514-7517.
PMID: 35539109 PMC: 9078427. DOI: 10.1039/c7ra13349a.
Lee S, Hong S, Yeo H, Hwang G RSC Adv. 2022; 10(32):18853-18859.
PMID: 35518342 PMC: 9053879. DOI: 10.1039/d0ra01651a.
Hwang G Molecules. 2018; 23(1).
PMID: 29316733 PMC: 6017082. DOI: 10.3390/molecules23010124.
Charge transfer dynamics in DNA revealed by time-resolved spectroscopy.
Fujitsuka M, Majima T Chem Sci. 2017; 8(3):1752-1762.
PMID: 28451299 PMC: 5396511. DOI: 10.1039/c6sc03428d.