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

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。

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

Catalyzed by Rhodococus sp. AJ270 whole cells, meso-dinitriles such as both endo-and exo-bicyclo2.2.1]-5-heptene-2,3-dinitriles and - bicyclo2.2.2]-5-octen-2,3-dinitriles were transformed into the corresponding dicarboxylic acids or their anhydrides whilst the racemic trans-bicyclo2.2.1]-5-heptene-2,3-dinitrile and trans- bicyclo2.2.2]-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.