Synthesis of oligonucleotides containing a new azobenzene fragment with efficient photoisomerizability.
The azobenzene derivatives possessing substituents of ROCH2CH2O- and-CH2CH2OR' or -CONHCH2CH2OR' at p,p'-positions, where R and R' are 4,4'-dimethoxytrityl and 2-cyanoethyl-N,N'-diisopropylphophoramidite, have been synthesized for linking two oligonucelotide segments. It has been found that the azobenzene linkers efficiently undergo trans-cis isomerization by exposing to UV light. The conversion efficiency showed slight dependence on structure or conformation of oligonucleotides attached to the azobenzene chromophore. The cis-form of the azobenzene in oligonucleotides was sufficiently stable at low temperature under dark. The present findings would open the way for light switch of nucleic acid structures.
Yamana
K
K
Department of Applied Chemistry, Himeji Institute of Technology, Hyogo, Japan. yamana@chem.eng.himeji-tech.ac.jp
Kan
K
K
Nakano
H
H
D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D001483:Base Sequence; D015195:Drug Design; D009682:Magnetic Resonance Spectroscopy; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D010777:Photochemistry; D013237:Stereoisomerism; D014466:Ultraviolet Rays
D001391:Azo Compounds; D009838:Oligodeoxyribonucleotides