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Captopril has structural similarity to the hydrolyzed penicillin product of metallo-β-lactamase catalysis (penicillinoic acid). (A) Outline of the mode of action of metallo-β-lactamases (MBLs). (B) Structures of the four captopril stereoisomers (2S,2S, 2S,2R, 2R,2S, and 2R,2R) and of d- and l-MBP. (C) Binding mode of hydrolyzed ampicillin with NDM-1 (PDB code 4HL2). (D) Binding mode of d-captopril with IMP-1 (PDB code 4C1G [described in this study]).
