Synthesis and Properties of the 5-Methyluridine Derivative of 3,4-Dihydro-2H-pyran-Bridged Nucleic Acid (DpNA)

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• 作者：Takashi Osawa ; Yoshiyuki Hari ; Masakazu Dohi ; Yuya Matsuda ; Satoshi Obika
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：80
• 期：21
• 页码：10474-10481
• 全文大小：426K
• ISSN：1520-6904

文摘

A novel 2鈥?O,4鈥?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.