Synthesis of the 5-Methyluridine Monomer of 3’-O,4’-C-Ethyleneoxy-Bridged Nucleic Acid

Osawa, Takashi; Dohi, Masakazu; Hitomi, Yuka; Ito, Yuta; Satoshi, Obika; Hari, Yoshiyuki

doi:10.3987/com-16-s(s)24

Cited by 4 publications

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“…We have previously developed several 3′,4′-bridged nucleic acids (3′,4′-BNAs, Figure ). − The sugar conformation of all 3′,4′-BNAs and trans -3′,4′-BNAs is an S-type. Shaikh et al developed a bicyclic 2′-deoxyribonucleoside with a 3′,4′-bridge structure, and X-ray crystal structural analysis revealed that the sugar conformation of the nucleoside was, interestingly, an N-type .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Duplex-Forming Ability, and Enzymatic Stability of Oligonucleotides Modified with Amide-Linked Dinucleotides Containing a 3′,4′-Tetrahydropyran-Bridged Nucleic Acid

Osawa,

Akino,

Obika

2023

J. Org. Chem.

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Replacement of a phosphodiester linkage with an amide linkage can improve the binding affinity of oligonucleotides to complementary RNA and their stability toward nucleases. In addition, restricting the conformation of the sugar moiety and the phosphate backbone in oligonucleotides effectively improves duplex stability. In this study, we designed amide-linked dinucleotides containing a 3′,4′-tetrahydropyran-bridged nucleic acid (3′,4′-tpBNA) with a constrained sugar conformation as well as a torsion angle ε. Phosphoramidites of the designed dinucleotides were synthesized and incorporated into oligonucleotides. Conformational analysis of the synthesized dinucleotides showed that the sugar conformation of the S-isomer of the amide-linked dinucleotide containing 3′,4′-tpBNA was N-type, which has the same conformation as that of the RNA duplex, while that of another R-isomer was S-type. T m analysis indicated that the oligonucleotides containing the synthesized S-isomer showed RNA-selective hybridizing ability, although their duplex-forming ability was slightly inferior to that of natural oligonucleotides. Interestingly, the stability of the oligonucleotides toward endonucleases was significantly improved by modification with the two types of amide-linked dinucleotides developed in this study.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Duplex-Forming Ability, and Enzymatic Stability of Oligonucleotides Modified with Amide-Linked Dinucleotides Containing a 3′,4′-Tetrahydropyran-Bridged Nucleic Acid

Osawa,

Akino,

Obika

2023

J. Org. Chem.

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

Osawa

Hitomi

Wakita

et al. 2018

Bioorganic & Medicinal Chemistry

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Generation of 4′-Carbon Radicals via 1,5-Hydrogen Atom Transfer for the Synthesis of Bridged Nucleosides

et al. 2022

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The rapid and facile generation of 4′-carbon radicals from oxime imidates of nucleosides via 1,5-hydrogen atom transfer induced by iminyl radicals was developed. The cyclization of 4′-carbon radicals with olefins, followed by the hydrolysis of imidate residues, provided various 2′-O,4′-C- and 3′-O,4′-C-bridged nucleosides. This operationally simple approach can be applied to the few-step syntheses of 6′S-methyl-2′-O,4′-C-ethylene-bridged 5-methyluridine (6′S-Me-ENA-T) and S-constrained ethyl-bridged 5-methyluridine (S-cEt-T).

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Synthesis of the 5-Methyluridine Monomer of 3’-O,4’-C-Ethyleneoxy-Bridged Nucleic Acid

Cited by 4 publications

References 0 publications

Synthesis, Duplex-Forming Ability, and Enzymatic Stability of Oligonucleotides Modified with Amide-Linked Dinucleotides Containing a 3′,4′-Tetrahydropyran-Bridged Nucleic Acid

Synthesis, Duplex-Forming Ability, and Enzymatic Stability of Oligonucleotides Modified with Amide-Linked Dinucleotides Containing a 3′,4′-Tetrahydropyran-Bridged Nucleic Acid

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

Generation of 4′-Carbon Radicals via 1,5-Hydrogen Atom Transfer for the Synthesis of Bridged Nucleosides

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