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化学学报
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化学学报 ›› 2001, Vol. 59 ›› Issue (10): 1827-1830. 上一篇    下一篇

研究论文

二腈的区域和对映选择性生物水解反应: 腈水合酶与二腈分子 作用模式初探

李建军;李纪生;王梅祥   

  1. 中国科学院化学研究所分子科学中心
  • 发布日期:2001-10-15

Regioselective and stereoselective biotransformations of dinitriles: A preliminary study of the action of nitrile hydratase on dinitriles

Li Jianjun;Li Jisheng;Wang Meixiang   

  • Published:2001-10-15

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在Rhodococcussp.AJ270细胞的催化作用下，内消旋的内式和外式双环[2.2.1]-庚烯-2,3-二腈和双环[2.2.2]-5-辛烯-2,3-二腈水解生成相应的二酸或酸酐，而外消旋的反式双环[2.2.1]-5-庚烯-2,3-二腈和双环[2.2.2]-5-辛烯-2,3-二腈则发生区域选择性和立体选择性的水解反应生成光活性的氰基酰胺和氰基羧酸。讨论了腈水合酶与二腈的作用模式。

关键词: 二腈, 选择性, 水解, 腈水合酶, 酰胺P, 水解酶

Catalyzed by Rhodococus sp. AJ270 whole cells, meso-dinitriles such as both endo-and exo-bicyclo[2.2.1]-5-heptene-2,3-dinitriles and - bicyclo[2.2.2]-5-octen-2,3-dinitriles were transformed into the corresponding dicarboxylic acids or their anhydrides whilst the racemic trans-bicyclo[2.2.1]-5-heptene-2,3-dinitrile and trans- bicyclo[2.2.2]-5-octene-2,3-dinitrile were converted regioselectiviely and stereoselectively to give the optically active monocyano amide and acid. The pattern of the nitrile hydratase action on the dinitrile substrates was also discussed.

Key words: SELECTIVITY, HYDROLYSIS, ITRILE-HYDRATASE, AMIDES P, HYDROLASE

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