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Synthesis of 2′-hydrazine oligonucleotides and their efficient conjugation with aldehydes and 1,3-diketones |
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| Authors: | Timofei S. Zatsepin Tatiana S. Oretskaya |
| Affiliation: | a Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, Moscow 119992, Russia b Medical Research Council Laboratory of Molecular Biology, Hills Road, Cambridge CB2 2QH, UK c School of Biomedical and Molecular Sciences, University of Surrey, Guildford, Surrey GU2 7XH, UK |
| Abstract: | Oligodeoxyribonucleotides that contain a novel nucleoside, 2′-O-(2-hydrazinoethyl)uridine, were synthesised by NaBH3CN reduction of hydrazones formed from 2′-O-(2-oxoethyl)oligonucleotides with FmocNHNH2, followed by concd aq NH3 deprotection. The 2′-hydrazine oligonucleotides obtained were then used to synthesise a number of conjugates with aldehydes via hydrazone formation and with1,3-diketones via pyrazole formation. The method was shown to be applicable for the preparation of oligonucleotide-peptide conjugates. |
| Keywords: | Modified oligonucleotides Conjugation Aldehyde 1,3-Diketone Hydrazone Pyrazole |
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