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Oligodeoxynucleotides Containing 2′‐Deoxy‐1‐methyladenosine and Dimroth Rearrangement |
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| Authors: | Edward?N Timofeev Sergey?N Mikhailov Andrei?N Zuev Ekaterina?V Efimtseva Piet Herdewijn Robert?L Somers Marc?M Lemaitre |
| Institution: | 1. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov str.?32, Moscow, 119991 Russia (phone: +7‐495‐1359733;2. fax: +7‐495‐1351405);3. Katholieke Universiteit Leuven, Rega Institute for Medical Research, Laboratory of Medicinal Chemistry, Minderbroedersstraat 10, B‐3000 Leuven, (phone: +32‐16‐337387;4. fax: +32‐16337340);5. Glen Research Corporation, 22825 Davis Drive, Sterling, VA, 20164, USA |
| Abstract: | 2′‐Deoxy‐1‐methyladenosine was incorporated into synthetic oligonucleotides by phosphoramidite chemistry. Chloroacetyl protecting group and controlled anhydrous deprotection conditions were used to avoid Dimroth rearrangement. Hybridization studies of intramolecular duplexes showed that introduction of a modified residue into the loop region of the oligonucleotide hairpin increases the melting temperature. It was shown that modified oligonucleotides may be easily transformed into oligonucleotides containing 2′‐deoxy‐N6‐methyladenosine. |
| Keywords: | Adenosine 1‐methyl‐2′ ‐deoxy‐ Protecting groups Oligonucleotides Dimroth rearrangement Nucleotides RNA |