title: Novel photoresponsive cross-linking oligodeoxyribonucleotides having a caged α-chloroaldehyde.
abstract: We have developed photoresponsive cross-linking oligodeoxyribonucleotides (ODNs) for sequence-selective interstrand covalent bond formation toward target nucleotides. A phosphoramidite derivative of α-chloroaldehyde whose carbonyl group was converted to a bis(2-nitrobenzyl)acetal group was prepared for the synthesis of photoresponsive α-chloroaldehyde (PCA)-conjugated ODN. The bis(2-nitrobenzyl)acetal group of a PCA-thymidine conjugate was completely removed by UV irradiation at 365 nm (400 mW/cm(2)) for 1 min. Photo-cross-linking studies revealed that PCA-ODN selectively reacted with the target nucleotides having an adenine or a cytosine moiety at the frontal position of the α-chloroaldehyde group.
authors.affiliation: Department of Biomolecular Engineering, Graduate School of Science and Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. akobori@kit.ac.jp
authors.forename: Akio
authors.initials: A
authors.lastname: Kobori
authors.forename: Takemune
authors.initials: T
authors.lastname: Yamauchi
authors.forename: Yuko
authors.initials: Y
authors.lastname: Nagae
authors.forename: Asako
authors.initials: A
authors.lastname: Yamayoshi
authors.forename: Akira
authors.initials: A
authors.lastname: Murakami
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D055668:Photochemical Processes; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry*; D014466:Ultraviolet Rays
chemical_list: D000447:Aldehydes; D003432:Cross-Linking Reagents; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; D017319:Photosensitizing Agents; C434331:phosphoramidite