Novel photoresponsive cross-linking oligodeoxyribonucleotides having a caged α-chloroaldehyde

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/cm2) 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.

We have developed photoresponsive cross-linking oligodeoxyribonucleotides for sequence-selective interstrand covalent bond formation toward target nucleotides.Figure optionsDownload as PowerPoint slide