Stereoselective catalysis of a retro-Michael reaction by class mu glutathione transferases. Consequences for the internal distribution of products in the active site.

Abstract excerpt

The reaction of glutathione (GSH) with trans-4-phenyl-3-buten-2-one (PBO) is readily reversible in aqueous solution with an apparent (pH-dependent) equilibrium constant at pH 8 of 6.4 x 10(2) M-1. Two class mu isoenzymes of GSH transferase from rat (M1-1 and M2-2) and two site specific mutants (M1-1/V9I and M2-2/I9V) catalyze the addition of GSH to PBO and the elimination of GSH from the two diastereomeric...

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