Synthesis and Properties of 2′‑O,4′‑C‑Ethyleneoxy Bridged 5‑Methyluridine

2′-O,4′-C-Ethyleneoxy bridged 5-methyluridine (EoNA-T), possessing a seven-membered linkage and an anomeric 4′-carbon, was synthesized and introduced into oligonucleotides by using an automated DNA synthesizer. The EoNA-modified oligonucleotides significantly stabilized the duplexes with single-stra...

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 14; pp. 3702 - 3705
Main Authors Hari, Yoshiyuki, Morikawa, Tomohiko, Osawa, Takashi, Obika, Satoshi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.07.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Circular Dichroism
DNA - chemistry
Oligonucleotides - chemical synthesis
Oligonucleotides - chemistry
Oligonucleotides, Antisense - chemistry
Physical Sciences
RNA - chemistry
Science & Technology
Uridine - analogs & derivatives
Uridine - chemical synthesis
Uridine - chemistry
PHOSPHOROTHIOATE
MONOMERS
NUCLEIC-ACID 2',4'-BNA
NUCLEOSIDE ANALOGS
5-METHYLCYTOSINE
STABILITY
THYMINE
CONFORMATIONAL-ANALYSIS
ADENINE
OLIGONUCLEOTIDES
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Summary:2′-O,4′-C-Ethyleneoxy bridged 5-methyluridine (EoNA-T), possessing a seven-membered linkage and an anomeric 4′-carbon, was synthesized and introduced into oligonucleotides by using an automated DNA synthesizer. The EoNA-modified oligonucleotides significantly stabilized the duplexes with single-stranded RNA and triplexes with double-stranded DNA relative to the natural oligonucleotide and oligonucleotides modified by another seven-membered bridged 5-methyluridine, 2′,4′-BNACOC-T. In addition, EoNA-T showed excellent nuclease resistance.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol401566r