O6-(ベンゾトリアゾル-1-イル) イノシン誘導体:簡単に合成され,反応性ニュクレオシド
Suyeal Bae1, Mahesh K Lakshman
1Department of Chemistry, The City College and The City University of New York, 138th Street at Convent Avenue, New York, New York 10031-9198, USA.
Journal of the American Chemical Society
|January 25, 2007
まとめ
新しい方法では,イノシンとBOP反応剤からO6-(ベンゾトリアゾル-1-イル) イノシン誘導体を合成します. これらの安定したヌクレオシド誘導体は,SNR反応とDNA改変に有効です.
科学分野:
- 有機化学 オーガニック・ケミストリー
- 核酸化学 核酸化学について
- 薬用化学 薬用化学について
背景:
- イノシンと2'-デオキシニノシンは基本的な核酸である.
- 新種のニュクレオシド誘導体の開発は,化学生物学と薬剤開発において極めて重要です.
- 改造された核酸化物の効率的な合成経路は,非常に求められています.
研究 の 目的:
- O6-(ベンゾトリアゾル-1-イル) イノシンとその2'-デオキシ誘導体を合成するための新しく便利な方法を開発する.
- これらの新しい核酸誘導体の反応性を調査する.
- サイト固有のDNA改変のためにDNAの構成要素を準備し,評価する.
主な方法:
- イノシンまたは2'-デオキシニノシンが1H-ベンゾトリアゾル-1-イロキシトリス (dimethylamino) フォスフォニウムヘキサフローロフォスファート (BOP) と反応する.
- 31P{1H} NMR.のような技術を使用して,中間物質と製品の分離と特徴付け.
- ダイマーおよびコンジュガートを含む様々なヌクレオシド誘導体の合成.
- DNA合成のためのフォスフォラミジットの構成要素の準備.
主要な成果:
- O6-(ベンゾトリアゾル-1-イル) イノシンと2'-デオキシイノシン誘導体の新種のクラスが成功して合成されました.
- これらの誘導体は,効果的な電友核酸化物として作用し,多様な核愛者と容易に反応する.
- アリル橋渡しダイマーや核酸-アミノ酸結合体などの複雑な構造が達成されました.
- フォスフォラミミドイトの誘導体が準備され,局所特異のDNA改変の可能性を示した.
結論:
- 単一の単純な方法により,安定した,反応性のあるリボおよび2'-デオキシリボヌクレオシド誘導体が得られます.
- これらのO6-(ベンゾトリアゾル-1-イル) イノシン誘導体は,SNR化学のための多用途のシントンである.
- ベンゾトリアゾリヌクレオシド・フォスフォラミドイトは,DNA改変のための有望な反応剤です.
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