Molecular Design of an Environmentally Sensitive Fluorescent Nucleoside, 3-Deaza-2'-Deoxyadenosine Derivative: Distinguishing Thymine by Probing the DNA Minor Groove

摘要

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 chargetransfer 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.