期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 18, 页码 7913-7922出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo301052v
关键词
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资金
- Ministry of Education, Culture, Sports, Science, and Technology (MEXT) Japan
- New Energy and Industrial Technology Development Organization (NEDO) Japan
- [21115008]
- Grants-in-Aid for Scientific Research [24790108, 21115008, 24105510] Funding Source: KAKEN
A method for the synthesis of P-stereodefined phosphorothioate oligoribonucleotides (PS-ORNs) was developed. PS-ORNs of mixed sequence (up to 12mers) were successfully synthesized by this method with sufficient coupling efficiency (94-99%) and diastereoselectivity (>= 98:2). The coupling efficiency was greatly improved by the use of 2-cyanoethoxymethyl (CEM) groups in place of the conventional TBS groups for the 2'-O-protection of nucleoside 3'-O-oxazaphospholidine monomers. The resultant diastereopure PS-ORNs allowed us to clearly demonstrate that an ORN containing an all-(Rp)-PS-backbone stabilizes its duplex with the complementary ORN, whereas its all-(Sp)-counterpart has a destabilizing effect.
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