Organic Synthesis Catalyzed by Plant Enzyme Hydroxynitrile Lyase

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  • Fuhshuku Ken-ichi
    Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University
  • Asano Yasuhisa
    Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University JST, ERATO

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  • 植物酵素ヒドロキシニトリルリアーゼが触媒する有機合成
  • ショクブツ コウソ ヒドロキシニトリルリアーゼ ガ ショクバイ スル ユウキ ゴウセイ

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Abstract

Hydroxynitrile lyase (HNL) is a key enzyme in the catabolism of cyanogenic glycosides in higher plants. HNL catalyzes the decomposition of cyanohydrins into corresponding aldehydes or ketones and HCN for defense against predators and microorganisms. The reverse reaction, synthesis of optically active cyanohydrins, has attracted the attention of scientists and industry.<br>We discovered several novel sources of HNL among 163 plant species in 74 families examined, using a simple HPLC-based method to determine the activity and stereoselectivity of HNLs. S-selective HNL (S-HNL) activity was found in a homogenate of the leaves of Baliospermum montanum, while R-selective HNLs (R-HNLs) were detected in the leaves and seeds of Passiflora edulis, and the seeds of Eriobotrya japonica, Prunus mume, Prunus persica, Chaenomeles sinensis and Sorbus aucuparia. The HNLs from P. edulis (PeHNL), E. japonica (EjHNL), P. mume (PmHNL), and B. montanum (BmHNL) have been purified to homogeneity and their enzymatic properties characterized.<br>In trying to expand the applicability of the HNL-catalyzed reaction, we focused on the potential for asymmetric synthesis. We describe the efforts to develop HNL-catalyzed reactions for the optically active cyanohydrin and β-nitro alcohol synthesis.

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