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Lucic, Anka; Malla, Tika R; Calvopiña, Karina; Tooke, Catherine L; Brem, Jürgen; McDonough, Michael A; Spencer, James; Schofield, Christopher J
Antibiotics (Basel), 03/2022, Letnik: 11, Številka: 3Journal Article
Carbapenems are important antibacterials and are both substrates and inhibitors of some β-lactamases. We report studies on the reaction of the unusual carbapenem biapenem, with the subclass B1 metallo-β-lactamases VIM-1 and VIM-2 and the class A serine-β-lactamase KPC-2. X-ray diffraction studies with VIM-2 crystals treated with biapenem reveal the opening of the β-lactam ring to form a mixture of the (2 )-imine and enamine complexed at the active site. NMR studies on the reactions of biapenem with VIM-1, VIM-2, and KPC-2 reveal the formation of hydrolysed enamine and (2 )- and (2 )-imine products. The combined results support the proposal that SBL/MBL-mediated carbapenem hydrolysis results in a mixture of tautomerizing enamine and (2 )- and (2 )-imine products, with the thermodynamically favoured (2 )-imine being the major observed species over a relatively long-time scale. The results suggest that prolonging the lifetimes of β-lactamase carbapenem complexes by optimising tautomerisation of the nascently formed enamine to the (2 )-imine and likely more stable (2 )-imine tautomer is of interest in developing improved carbapenems.
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