Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 14, Pages 4599-4604Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202003528
Keywords
crosslinking; nucleobase modification; photochemistry; serinol nucleic acid; XNA
Categories
Funding
- AMED [19am0401007]
- JSPS KAKENHI [JP18H03933, JP20K15399, JP20J15414]
- JSPS A3 Foresight Program
- Asahi Glass Foundation
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The research demonstrates the orthogonal photo-regulation of double-strand formation between serinol nucleic acid (SNA) and RNA using different wavelengths of light and new photo-reactive nucleobases. By utilizing specific photo-switches, four hybridization states of two SNA/RNA duplexes could be orthogonally photo-controlled.
Wavelength-selective photo-regulation by multiple chromophores responding to different wavelengths can expand the variation of photo-manipulating systems. Herein, we report the orthogonal photo-regulation of duplex formation between serinol nucleic acid (SNA) and RNA using light-induced crosslinking reactions mediated by a new photo-reactive nucleobase 8-naphthylvinyladenine ((NV)A) and previously described 8-pyrenylvinyladenine ((PV)A). An intrastrand crosslink was induced in an SNA strand containing two adjacent (NV)A residues by irradiation with 340-405 nm light; the crosslink was reversed by irradiation with <= 300 nm light. In an SNA strand with adjacent (NV)A and (PV)A residues, an intrastrand crosslink resulted from irradiation with 405-465 nm light that was reversed by irradiation with <= 340 nm light. Intrastrand photo-crosslinking caused severe destabilization of an SNA/RNA duplex, resulting in dissociation to single strands. Cycloreversion resulted in duplex formation. With these (NV)A/(NV)A and (NV)A/(PV)A photo-switches, four hybridization states of two SNA/RNA duplexes could be orthogonally photo-controlled by irradiation with a suitable wavelength of light.
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