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

Catalyzed by Rhodococcus sp. AJ270 whole cells, meso - dinitriles such as b oth endo - and exo bicyclo [ 2. 2. 1 ] - 5 - heptene - 2, 3 - dinitriles en d - bicyclo [ 2. 2. 2 ] - 5 - octene - 2, 3 - dinitriles were transformed i nto the corresponding dicarboxylic acids or their anhydrides whilst the rac emic trans - bicyclo [2. 2. 1 ] - 5 - heptene - 2,3 - dinitrile and trans - bicyclo [ 2. 2. 2] - 5 - octene - 2,3 - dinitrile were converted regiosele ctively and stereoselectively to give the optically active monocyano amide and acid. The pattern of the nitrile hydratase action on the dinitrile subs trates was also discussed.