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A mixed disulfide reagent for photolabeling is described which reacts stoichiometrically with a cysteine sulfhydryl group of rabbit muscle creatine kinase to form a new mixed disulfide between enzyme and 2-thiobenzyl[14C]diazoacetate. When irradiated at 254 nm for 5 s in a photoreactor, the enzyme-bound diazo group is destroyed, presumably via a carbene intermediate. After photolysis, the enzyme can only be 69+/-2% reactivated by dithiothreitol, and only 67+/-1% of the radiolabel can then be removed from the protein by dialysis in the presence of dithiothreitol.
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