A synthetic route to the C-nucleoside that bears benzophenone
as a DNA base substitution directly at the anomeric center of the
2′-deoxyribofuranoside was worked out. Furthermore, the α-anomer
of this artificial nucleoside was converted synthetically into the
corresponding DNA building block and incorporated into two representative
oligonucleotides by automated phosphoramidite chemistry. The chromophore-modified
DNA was characterized by methods of optical spectroscopy. The absorption
band at ∼350 nm can be used for selective excitation of
the benzophenone chromophore outside the nucleic acid absorption
range, which makes the benzophenone nucleoside potentially useful
for photochemical and photobiological applications.
DNA - oligonucleotide - phosphorescence - photocatalysis - sensitizer
