アルドラーゼを用いた糖類合成の展開 Recent Advances in Aldolase-Catalyzed Synthesis of Unnatural Sugars and Iminocyclitols

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Facile chemoenzymatic methods for the synthesis of a variety of D- and L- iminocyclitols or L-sugars have been developed. The practicality of formerly reported methods using dihydroxyacetone phosphate (DHAP) aldolase was limited by the high cost and instability of DHAP. Here we discuss three strategies toward the facile synthesis of sugar analogues using DHA(P) aldolases from readily available non-phosphoryrated donor substrates. (1) Directed evolution of the L-rhamnulose 1-phosphate aldolase (RhaD) was employed to alter the donor substrate specificity of RhaD aldolase from DHAP to DHA. In vivo selection for the directed evolution using genetically engineered E. coli strain was constructed . (2) RhaD aldolase was found to accept non-phosphorylated dihydroxyacetone (DHA) as a donor substrate in the presence of borate. We applied this discovery to develop a practical one-step synthesis of L-fructose and two-step synthesis of L-iminocyclitols . (3) A one-pot synthesis was achieved using the recently discovered D-fructose 6-phosphate aldolse (FSA). FSA utilized DHA, hydroxyacetone, and 1-hydroxy-2-butanone as donor substrates to allow the synthesis of a variety of novel D-iminocyclitols in a concise fashion.

収録刊行物

  • 有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN  

    有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN 66(6), 605-615, 2008-06-01 

    The Society of Synthetic Organic Chemistry, Japan

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各種コード

  • NII論文ID(NAID)
    10021175615
  • NII書誌ID(NCID)
    AN0024521X
  • 本文言語コード
    JPN
  • 資料種別
    ART
  • ISSN
    00379980
  • NDL 記事登録ID
    9545078
  • NDL 雑誌分類
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL 請求記号
    Z17-256
  • データ提供元
    CJP書誌  NDL  J-STAGE 
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