サイクロンチオスルフィナートとサイクロンジソルフィドは,単離チオルの修正を避けながら,選択的にクロスリンクチオル
Daniel P Donnelly1,2, Matthew G Dowgiallo1, Joseph P Salisbury1,2
1Department of Chemistry and Chemical Biology , Northeastern University , 360 Huntington Avenue , Boston , Massachusetts 02115 , United States.
Journal of the American Chemical Society
|June 1, 2018
まとめ
新しい循環型チオスルフィナートは,正確なチオルクロスリンクを提供し,有毒な副産物を避け,効率的なマクロ分子研究とポリマー合成を可能にします. これらの強力で細胞に浸透するクロスリンクは 生物学的条件下で効果的に機能します
科学分野:
- 化学生物学
- 有機化学
- 生物化学
背景:
- 現代のチオール選択クロスリンクは,しばしば有毒な"死角"の改変をもたらします.
- これらの望ましくない副産物は,マクロ分子構造の研究とポリマー合成を複雑にします.
研究 の 目的:
- 選択的なチオルのクロスリンクのための新しい化学的ツールを開発する.
- 既存のクロスリンクエージェントの限界を克服し,デッドエンドの修正を最小限に抑える.
主な方法:
- 試験のためにチオール対の銅/亜鉛超酸化物ディスミュータゼ (SOD1) を利用した.
- 反応メカニズムを理解するために,密度関数理論 (DFT) の計算を使用した.
- 合成した5~7基のサイクリックチオスルフィネート
主要な成果:
- リポ酸のような循環性ジスルフィードは,行き詰った製品なしで効率的なチオールペアクロスリンクを示した.
- モノ-S-オクソ誘導体 (循環型チオスルフィナート) は,循環型ジスルフィードと比較して10^4倍までクロスリンクを加速した.
- 新しいチオスルフィナートクロスリンクは,グルタチオンの存在で細胞の浸透性,効能,および機能性を示した.
結論:
- 循環型チオスルフィナートは,高効率で選択的なチオルクロスリンク剤の新種である.
- これらの化合物は,高収量,直角性,および水との互換性を含む,クリックのような属性を示す.
- 開発されたクロスリンクは細胞内応用と高度なポリマー合成に適しています.
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