4.7 Article

Synthesis and hybridizing properties of isoDNAs including 3 '-O,4 '-C-ethyleneoxy-bridged 5-methyluridine derivatives

Journal

BIOORGANIC & MEDICINAL CHEMISTRY
Volume 26, Issue 14, Pages 3875-3881

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2018.05.043

Keywords

Bridged nucleic acids; Nucleosides; Oligonucleotides; isoDNAs; Sugar modifications; UV-melting experiments

Funding

  1. JSPS KAKENHI [JP17K18295]
  2. Uehara Memorial Foundation, Japan

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3',4'-Ethyleneoxy-bridged 5-methyluridine derivatives with methyl groups in the bridge, (R)-Me-3',4'-EoNA-T and (S)-Me-3',4'-EoNA-T, were synthesized, and these two analogs and unsubstituted 3',4'-EoNA-T were successfully incorporated into a 2',5'-linked oligonucleotide (isoDNA). Their duplex-forming ability with complementary DNA and complementary RNA, and triplex-forming ability with double-stranded DNA, were evaluated by UV-melting experiments. The results indicated that isoDNAs, including these 3',4'-EoNA analogs, could hybridize exclusively with complementary RNA. In particular, 3',4'-EoNA-T and (R)-Me-3',4'-EoNA-T modifications within isoDNA could stabilize the duplexes with complementary RNA compared with unmodified or 3',4'-BNA-modified isoDNAs.

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