エント・オキシコドンの化学酵素総合合成:第2,第3,第4世代の戦略
Mariia Makarova1, Mary Ann A Endoma-Arias1, Helen E Dela Paz1
1Department of Chemistry and Centre for Biotechnology , Brock University , 1812 Sir Isaac Brock Way , St. Catharines , Ontario L2S 3A1 , Canada.
Journal of the American Chemical Society
|June 12, 2019
まとめ
エントオキシコドンのための4つの新しい合成経路は,生物由来の出発材料を使用して開発されました. これらの戦略は,オピオイド類の化学合成の進歩を示しています.
科学分野:
- 有機化学
- 合成化学
- バイオテクノロジー
背景:
- オピオイドの合成は 複雑な課題を提示しています
- オピオイドの類似品への効率的な経路の開発は研究にとって極めて重要です.
- バイオベースの材料は持続可能な経路を提供します.
研究 の 目的:
- エントオキシコドンの4つの異なる合成を設計し,実行する.
- エントオキシコドンコアを製造するための異なる合成戦略を調査し,比較する.
- エンジニアリングされた大腸菌によって生成された生物由来中間物質を使用する.
主な方法:
- E. coli JM109 (pDTG601A) を使用したフェネチルアセテートの全細胞発酵により,重要なダイネジオール中間産物が生成される.
- SmI2媒介サイクリング,ヘンリー反応,アジデーション-ラクトーム形成,およびC-9/C-14結合構造のためのケト-ニトロンの還元結合の適用.
- 初期世代の合成において,Dリング形成のためのパーカーのサイクルを活用する.
主要な成果:
- エントオキシコドンを4つの世代で 合成した
- 第4世代の合成は11つの操作 (18段階) で完了し,最も効率的でした.
- それぞれの世代は キー・ボンド・フォーメーションと リング・コンストラクションの ユニークな戦略を示しました
結論:
- この研究は,合成戦略のエントオキシコドンへの進歩を示し,効率の向上を強調しています.
- バイオ発酵による原料の使用は持続可能なアプローチを示しています.
- 詳細な実験データとスペクトルデータは,すべての新しい化合物について提供され,さらなる研究を容易にする.
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