Synthesis and properties of thymidines with six-membered amide bridge |
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Authors: | Yoshiyuki Hari Takashi Osawa Yutaro Kotobuki Aiko Yahara Ajaya R Shrestha Satoshi Obika |
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Institution: | Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan |
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Abstract: | Artificial thymidine monomers possessing amide or N-methylamide bridges were designed, synthesized, and introduced into oligonucleotides. UV-melting experiments showed that these oligonucleotides preferred single-stranded RNA (ssRNA) to single-stranded DNA (ssDNA) in duplex formation. Both amide- and N-methylamide-modified oligonucleotides led to a significant increase in the binding affinity to ssRNA by up to +4.7 and +3.7 °C of the Tm value per modification, respectively, compared with natural oligonucleotide. In addition, their oligonucleotides showed high stability against 3′-exonuclease. |
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Keywords: | Bridged nucleic acids Nucleosides Nucleotides Oligonucleotides Sugar modifications |
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