(Z,Z,Z,Z,Z,E,E,ω) -ヘプタプレノールの合成とNMR特徴付け
Dusan Hesek1, Mijoon Lee, Jaroslav Zajíček
1Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Journal of the American Chemical Society
|August 7, 2012
まとめ
新しい合成により,バクテリアの細胞包膜バイオシンセシスを研究するための重要な化合物である (Z(4),E(2),ω) -ヘプタプレノールのマルチグラム量が得られる. この方法は,効率的な生産のために,ネロール由来スルフォン中間物質を使用しています.
科学分野:
- 有機化学 オーガニック・ケミストリー
- バイオケミストリー バイオケミストリー
- 微生物学 微生物学とは
背景:
- バクテリアの細胞膜は,細菌の生存に不可欠であり,抗微生物開発のターゲットです.
- 細胞包膜の構成要素の生物合成を理解することは,新しい治療戦略の開発に不可欠です.
研究 の 目的:
- (Z(4),E(2),ω) -ヘプタプレノールの実用的なマルチグラム合成を開発する.
- バクテリア細胞封筒の生物合成を研究するための重要な反応剤を提供すること.
主な方法:
- ネロール由来スルフォン中間物質を用いた (Z(4),E(2),ω) -ヘプタプレノールの合成.
- サルフォン中間産物から5段階の変換で,総収量は18%です.
- 構造確認のためのNMRシフト反応剤として,ヨーロッパウム (III) トリス (Tris) [3-[2-チエニル]-1,1,1,5,5,5-ヘクサフッロロペンタンダイオナート] (Eu (hfc) 3) を利用した.
主要な成果:
- (Z(4),E(2),ω) -ヘプタプレノールをマルチグラムで合成することに成功しました.
- NMRスペクトロスコピーを用いて,標的化合物の構造とステレオ化学を確認しました.
- 合成反応の主要な副産物の構造を特定し,割り当てました.
結論:
- 記述された合成経路は,かなりの量の (Z(4),E(2),ω) -ヘプタプレノールを得るための信頼できる方法を提供します.
- このヘプタプレノールのアクセシブルな供給は,バクテリアの細胞包膜バイオシンセシスのさらなる研究を促進します.
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