書誌事項
- タイトル別名
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- Stereocontrolled Synthesis of Phosphate-modified Oligonucleotides
- リン ゲンシ シュウショク オリゴ カクサン ノ リッタイ センタクテキ ゴウセイ
- 公開日
- 2016
- 資源種別
- journal article
- DOI
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- 10.5059/yukigoseikyokaishi.74.31
- 公開者
- 公益社団法人 有機合成化学協会
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説明
Phosphate-modified oligonucleotides in which one of the two non-bridging oxygen atoms of each phosphodiester linkage is replaced by other kinds of atoms or substituents are useful as the basic structures of therapeutic oligonucleotides. These oligonucleotides have stereogenic phosphorus atoms and the development of an efficient method for the stereocontrolled synthesis is one of the unsolved problems. To solve this problem, we developed a novel method using diastereopure nucleoside 3’-O-oxazaphospholidine derivatives as monomers. Proline-derived bicyclic oxazaphospholidine derivatives were found to be the monomers of choice in that they could be synthesized with diastereoselectivity of >99 : 1 and were stable to epimerization. Various phosphate-modified oligonucleotides were synthesized in a stereocontrolled manner by using these monomers. The resultant stereoregulated oligonucleotides enabled us to demonstrate that the hybridizing affinity for complementary RNA was greatly affected by the configuration of the phosphorus atoms.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 74 (1), 31-44, 2016
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390282680317437824
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- NII論文ID
- 130005126249
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 027053616
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- 本文言語コード
- ja
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- 資料種別
- journal article
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- データソース種別
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- JaLC
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