Efficient conjugation and preferential DNA binding of oligonucleotides containing 2′-O-(2-oxoethyl)arabinouridine |
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Authors: | Timofei S Zatsepin Dmitry A Stetsenko Tatiana S Oretskaya |
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Institution: | a Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory, Moscow 119992, Russia b MRC, Laboratory of Molecular Biology, Hills Road, Cambridge CB2 2QH, UK |
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Abstract: | Oligodeoxyribonucleotides were synthesized that contain a novel nucleoside, 2′-O-(2-oxoethyl)arabinouridine. Whereas such oligonucleotides showed only a slight reduction in the TM values of their complexes with complementary DNA, a significant destabilization was observed in the case of duplexes formed with RNA. This may be explained by the C2′-endo conformation of 2′-O-(2,3-dihydroxypropyl)arabinouridine as demonstrated by NMR experiments in D2O. The modified oligonucleotides were used to synthesize a number of conjugates with dyes, biotin and a N-modified laminin peptide, by hydrazone and oxime formation. We suggest that the 2′-arabinoaldehyde-containing DNA duplexes may be valuable tools for affinity modification of DNA-binding proteins. |
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Keywords: | Modified oligonucleotides Conjugation Aldehyde Oxime Hydrazone |
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