Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 27, Issue 8, Pages 1728-1741Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2019.02.034
Keywords
Bridged nucleic acids; Nucleotides; Oligonucleotides; Sugar modifications
Funding
- advanced research for medical products mining program of the National Institute of Biomedical Innovation (NIBIO)
- Japan Science and Technology Agency, Creation and Support Program for Start-ups from Universities
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We efficiently synthesized 2'-O,4'-C-aminomethylene-bridged nucleic acid (2',4'-BNA(NC)) monomers bearing the four nucleobases, guanine, adenine, thymine, and 5-methylcytosine and incorporated these monomers into oligonucleotides. Initially, we carried out the transglycosylation reaction on several 2'-O-substituted 5-methyluridines to evaluate the effects of 2'-substitutions on this reaction. Under the optimized conditions, purine nucleobases were successfully introduced, and 2',4'-BNA(NC) monomers bearing adenine or guanine were obtained over several steps. In addition, the improved synthesis of the 2',4'-BNA(NC) monomers bearing thymine or 5-methylcytosine was also achieved. The obtained 2',4'-BNA(NC) monomers were subsequently incorporated into oligonucleotides and the duplex-forming abilities of the modified oligonucleotides were investigated. Duplexes containing 2',4'-BNA(NC) monomers in both or either strands were found to possess excellent thermal stabilities.
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