Visible-Light-Triggered Cross-Linking of DNA Duplexes by Reversible [2+2] Photocycloaddition of Styrylpyrene.
Reversible photo-cross-linking of a DNA duplex through the [2+2] photocycloaddition of styrylpyrene is reported. Styrylpyrene moieties on d-threoninol linkers were introduced into complementary positions on DNA strands. Irradiation of the styrylpyrene pair in the duplex with visible light at λ=455 nm induced a [2+2] photocycloaddition between styrylpyrenes that cross-linked the two strands of the duplex. Two diastereomers were formed after [2+2] photocycloaddition as a result of rotation of the styrylpyrene residues. Also, the cycloreversion reaction was induced by UV light at λ=340 nm, which reversibly yielded the uncross-linked strands.
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8603, Japan.
Tetsuya
T
Doi
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8603, Japan.
Hayato
H
Kawai
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8603, Japan.
Keiji
K
Murayama
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8603, Japan. kashida@nubio.nagoya-u.ac.jp.|PRESTO (Japan) Science and Technology Agency, 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012, Japan. kashida@nubio.nagoya-u.ac.jp.
Hiromu
H
Kashida
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8603, Japan. asanuma@nubio.nagoya-u.ac.jp.
Hiroyuki
H
Asanuma
D000605:Amino Alcohols / Q000737:chemistry; D001483:Base Sequence; D002072:Butylene Glycols / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003432:Cross-Linking Reagents / Q000737:chemistry*; D003500:Cyclization; D061565:Cycloaddition Reaction; D004247:DNA / Q000737:chemistry*; D008027:Light; D009690:Nucleic Acid Conformation; D055668:Photochemical Processes; D011721:Pyrenes / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013343:Styrenes / Q000737:chemistry*; D014466:Ultraviolet Rays
D000605:Amino Alcohols; D002072:Butylene Glycols; D003432:Cross-Linking Reagents; D011721:Pyrenes; D013343:Styrenes; C532652:threoninol; D004247:DNA
DNA; cross-linking; cycloaddition; cycloreversion; photochemistry