Photochromic DNA having fluorescent protein-inspired nucleosides

[Display omitted] •Fluorescent protein-inspired nucleosides “FIN” were developed.•FINs were readily incorporated to DNA using phosphoramidite chemistry.•Thermodynamic properties of DNA were changeable by UV irradiation. Molecular switches controlled by light stimuli can be applicable to the variety...

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Bibliographic Details
Published in:Tetrahedron letters 2018-10, Vol.59 (41), p.3690-3693
Main Authors: Kobori, Akio, Arai, Taichiro, Sakata, Yuya, Sugita, Takayuki, Yamayoshi, Asako, Murakami, Akira
Format: Article
Language:English
Subjects:
DNA
Fluorescent protein
Photochromic nucleoside
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Summary:[Display omitted] •Fluorescent protein-inspired nucleosides “FIN” were developed.•FINs were readily incorporated to DNA using phosphoramidite chemistry.•Thermodynamic properties of DNA were changeable by UV irradiation. Molecular switches controlled by light stimuli can be applicable to the variety of the biological application. In this study, skeletal structures of a chromophore of fluorescent protein were applied as aglycones of newly designed photochromic nucleosides, “Fluorescent protein-inspired nuceloside: FIN”. Phosphoramidite units of the photochromic nucleosides having imidazolinone derivatives with benzylidene or 3-pyridilidene groups were successfully synthesized for FIN-containing ODNs. Thermodynamic studies of the FIN-containing ODNs revealed that photo-irradiation with specific wavelength induced stability change of the duplexes.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.08.064