オリゴマンノシドモデル化合物におけるサッカリド単位間のアセチル群の移動

Robert Lassfolk¹, Jani Rahkila¹, Mikael P Johansson^2,3

¹Johan Gadolin Process Chemistry Centre, Laboratory of Organic Chemistry, Åbo Akademi University , FI-20500 Åbo , Finland.

Journal of the American Chemical Society

|December 27, 2018

まとめ

オリゴサッカライドにおけるアセチル群の移動は,これまで考えられていたよりも複雑である. この研究ではアセチル基は糖分単位の間だけでなく糖分単位の間にも移動することが示されています

科学分野:

炭水化物の化学
生物化学
有機合成

背景:

アセチル化オリゴサッカライドは自然に多く存在し,生物学的プロセスに作用する.
これらの構造におけるアセチル群の移動は十分に理解されていない.
アセチル群の移動の複雑さはほとんど気づかれていません

研究の目的:

オリゴサッカライドにおけるアセチル群の移動現象を調査する.
アセチル群の移動の複雑性と範囲を決定する.
アシレート炭水化物の潜在的な生物学的影響を調査する.

主な方法:

オリゴマンノシドモデル化合物の有機合成
構造分析のための核磁気共振 (NMR) スペクトロスコーピー.
反応メカニズムを理解するための量子化学モデリング

主要な成果:

アセチル群の移動は,以前に認識されたより複雑なプロセスであることを示した.
異なるサッカリド単位間のグリコシド結合の間のアセチル群の移動を初めて示した.
移動が単一のモノサッカライド部分に限定されない証拠を提供した.

結論:

オリゴサッカライドとポリサッカライドのアセチル群の移動は,異なる糖分単位の間に起こる可能性があります.
この発見は,炭水化物のアサイル化に関する以前の理解に異議を唱える.
自然界におけるアシル化炭水化物の生物学的意義に関する新しい疑問を提起する.

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