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Synthesis of an Intein-mediated Artificial Protein Hydrogel
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モノメリック・ストリープタヴィジン人工メタロ酵素による非対称 δ-ラクトーム合成
Isra S Hassan1, Angeline N Ta2, Michael W Danneman1,2
1Department of Chemistry , Columbia University , New York , New York 10027 , United States.
Journal of the American Chemical Society
|March 14, 2019
まとめ
この研究は,価値あるラクトームの非対称合成のための新しい人工メタロ酵素を導入します. 設計されたモノメリック・ストリープタヴィジンRh (III) 触媒は,穏やかな条件下で高い効率とステレオ制御を示しています.
科学分野:
- カタリシス
- 有機合成
- バイオテクノロジー
背景:
- 新しい化学変換のための人工メタロ酵素 (ARM) の設計は大きな課題です.
- ストレプタヴィジンベースのARMは,安定性と調整可能な活性部位により,触媒のための有望なプラットフォームを提供します.
研究 の 目的:
- 非対称な合成のためのモノメリックストレプタヴィジンRh ((III)) 人工金属酵素を開発する.
- 設計されたArMのC-H活性化と [4+2] キャンセル反応の触媒効率とステレオ選択性を調査する.
主な方法:
- Rh ((III) サイクロペンタディエニル (Cp*) 触媒を埋め込んだモノメリック・ストリープタヴィジン (mSav) 構造.
- タンデムC-H活性化と [4+2]無効化によるα,β-不飽和δ-ラクトームの非対称合成
- 反応産物の産量とエナティオメア過剰の特徴づけ
主要な成果:
- mSav-Rh(III) ArMは,α,β-不飽和δ-ラクトームの非対称合成を可能にし,99%までの収量と97%までのエナティオメア過剰を可能にしました.
- ARMは室温で水分状態で効率的に動作します.
- mSav-Rh触媒は,孤立したコファクターと比較して,反応性 (7倍) とステレオコントロールが著しく向上した.
- モノメリックのArMは,テトラメリックのストリープタヴィジン-Rhの変種よりも反応性が優れていた (11- 33倍).
結論:
- 開発された単体シュレプトアヴィジンRh (III) ArMは,δ- ラクタムの非対称合成のための非常に効果的な触媒である.
- このARMは 医薬品の重要な構成要素である 酵素濃縮ピペリジンへのアクセスに 強力なプラットフォームを提供します
- この研究は,人工メタロ酵素における触媒性能の改善のためのモノメリック・スキャフォードの利点を強調している.
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