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. Author manuscript; available in PMC: 2017 Sep 28.
Published in final edited form as: J Am Chem Soc. 2016 Sep 14;138(38):12527–12533. doi: 10.1021/jacs.6b06823

Figure 1.

Figure 1

A. Proposed catalytic cycle for heme protein-catalyzed carbene transfer to an olefin starts from the reduced ferrous state, which undergoes reaction with a diazo compound to form the putative iron carbenoid. The carbenoid reacts with an olefin, forming the cyclopropane product and regenerating the ferrous heme protein. B. Proposed mechanism-based inactivation via (a) porphyrin and (b) side chain modification involving the same iron carbenoid intermediate that mediates productive olefin cyclopropanation.