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Cyclization catalyzed by both HalM2 and NisC is reversible, as shown with α-D-labeled mHalA2 and mNisA. D/H exchange in α-D-labeled mHalA2 occurs in the presence of HalM2 but could occur either by a deprotonation/reprotonation mechanism or by a reversible cyclization mechanism. The reversibility of cyclization was confirmed for α-D-labeled mHalA2 and mNisA by trapping of the ring-opened species by conjugate addition to NEM.238
