バイオミメティック・シンセシスは,プレアイソラクトンAの起源を明らかにする
Alexander J E Novak1, Claire E Grigglestone1, Dirk Trauner1
1Department of Chemistry , New York University , Silver Center, 100 Washington Square East, Room 712 , New York , New York 10002 , United States.
Journal of the American Chemical Society
|September 14, 2019
まとめ
研究者らは,真菌の代謝物質であるプロイゾラクトンAのバイオミメティック合成を開発した. この研究は,その血中性質を明らかにし,それを提案します
科学分野:
- 有機化学
- 自然製品合成
- キノコの代謝
背景:
- プリューアイソラクトンAは,生物合成起源が不完全な真菌代謝産物である.
- 以前の構造的割り当てはセスキートペノイドの分類を示唆したが,その分離は問題となった.
- 生物模倣的アプローチは,天然の製品構造と生物合成経路の解明に価値があります.
研究 の 目的:
- プルーアイソラクトンAへの簡潔で生体模倣的な合成経路を開発する.
- 合成のステレオ化学的結果を調査し,レースメイトとして自然に発生するプレウアイソラクトンAを説明する.
- プルーアイソラクトンAの生物合成起源と分類を再評価する.
主な方法:
- 主なステップとして,プルポルガリン型 (5 + 2) -サイクロアディションを使用するバイオミメティック戦略.
- その後の断片化,ビニロゲスアルドール添加,酸化性乳酸化,ベンジル酸再配列が利用された.
- 合成配列は潜在的生物合成変換を模倣するように設計された.
主要な成果:
- プルーアイソラクトンAの短時間かつ効率的な生体模倣合成が成功しました.
- 合成経路は自然にラセミック製品につながり,観察された自然発生を説明します.
- 提案されたメカニズムは,フェノールポリケチドの起源を好み,セスキートペノイド分類に挑戦しています.
結論:
- 開発された合成経路は,プルーアイソラクトンAにアクセスするための新しい効率的な方法を提供します.
- この研究は,レースメイトとしてプルーアイソラクトンAを分離するためのメカニズム的根拠を提供します.
- 証拠は,プロイソラクトンAがセスキーターペノイドではなくフェノールポリケチドであることを強く示唆しており,その生物合成起源の見直しが必要である.
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