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Chembiochem. 2014 Jul 21;15(11):1638-44. doi: 10.1002/cbic.201402078. Epub 2014 Jul 8.

Molecular design of an environmentally sensitive fluorescent nucleoside, 3-deaza-2'-deoxyadenosine derivative: distinguishing thymine by probing the DNA minor groove.

Author information

1
Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Koriyama, Fukushima 963-8642 (Japan).

Abstract

An environmentally sensitive fluorescent nucleoside containing a 3-deazaadenine skeleton has been developed, and its photophysical properties were investigated. Newly developed C3-naphthylethynylated 3-deaza-2'-deoxyadenosine ((3nz) A, 1) exhibited dual fluorescence emission from an intramolecular charge-transfer state and a locally excited state, depending upon molecular coplanarity. DNA probes containing 1 clearly discriminated a perfectly matched thymine base on the complementary strand by a distinct change in emission wavelength.

KEYWORDS:

DNA; bioorganic chemistry; deazaadenine; fluorescent nucleosides; naphthalene

PMID:
25044623
DOI:
10.1002/cbic.201402078
[Indexed for MEDLINE]

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