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Electron Injection into DNA: Synthesis and Spectroscopic Properties of Pyrenyl‐Modified Oligonucleotides
Author(s) -
Amann Nicole,
Pandurski Evgeni,
Fiebig Torsten,
Wagenknecht HansAchim
Publication year - 2002
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 - 10.1002/1521-3765(20021104)8:21<4877::aid-chem4877>3.0.co;2-p
Subject(s) - nucleobase , moiety , oligonucleotide , chemistry , phosphoramidite , uracil , electron transfer , dna , photochemistry , covalent bond , nucleoside , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry
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.