Synthesis and Properties of the 5-Methyluridine Derivative of 3,4-Dihydro-2H-pyran-Bridged Nucleic Acid (DpNA).
J Org Chem
; 80(21): 10474-81, 2015 Nov 06.
Article
em En
| MEDLINE
| ID: mdl-26431393
ABSTRACT
A novel 2'-O,4'-C-bridged nucleic acid, 3,4-dihydro-2H-pyran bridge moiety (DpNA), with a dioxabicyclo[3.2.1]oct-3-ene ring was designed. Construction of the dihydropyran bridge was achieved by dehydration of a six-membered hemiacetal ring, and the DpNA monomer was synthesized in 10 steps from 5-methyluridine (total yield 9%). The synthesized DpNA monomer was incorporated into oligonucleotides to examine the properties of the modified oligonucleotides. The DpNA-modified oligonucleotides possessed high affinity toward ssRNA and were more resistant to nucleases compared to the corresponding natural oligonucleotide.
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Base de dados:
MEDLINE
Assunto principal:
Oligonucleotídeos
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Piranos
/
Uridina
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Hidrocarbonetos Aromáticos com Pontes
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RNA
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Oligonucleotídeos Antissenso
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article