Abstract
Abstract[methine‐3H]1,1‐Di‐(4‐chlorophenyl)‐2,2,2‐trichloroethane ([methine‐3H]DDT) and its di‐(4‐nitrophenyl) analog, both of high purity with a moderately high specific activity were prepared. Chlorobenzene was condensed with [1‐3H]1‐(4‐chlorophenyl)‐2,2,2‐trichloro‐ethanol, which had been synthesized by sodium boro[3H]hydride reduction of 4‐chlorophenyl trichloromethyl ketone. The purified [3H]DDT had a specific activity of 0.77 Ci/mmol (28.49 GBq/mmo 1). [methine‐3H]1, 1‐Diphenyl‐2,2,2‐trichloroethane was similarly synthesized and was nitrated to give [methine‐3H]1,1‐di‐(4‐nitrophenyl)‐2,2,2‐trichloroethane of 1.63 Ci/mmol (60.31 GBq/mmol). Dehydrochlorination with housefly enzyme (glutathione‐dependent DDT dehydrochlorinase) showed a remarkable isotope effect. For DDT, the observed tritium isotope effect on Vmax/Km was 11.51±0.52. For the nitro‐analog, the value was 11.3±1.2. We measured deuterium isotope effect on Vmax/Km for DDT in a competitive mode and obtained the value 4.19±0.34. Based on these values, the magnitude of intrinsic isotope effect values on DDT‐dehydrochlorination reaction was discussed.
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