Ovothiol and ergothioneine are histidine thiol derivatives. Their biosynthesis involve an extremely efficient trans-sulfuration strategy: a non-heme iron enzyme catalyzed oxidative coupling between cysteine and histidine/hercynine and a PLP-dependent C-S lyase catalyzed reductive C-S lyase reaction. By making use of mass spectrometry as one of the key tools, we characterized several of the mechanistic features of these two key steps in ovothiol and ergothioneine biosyntheses, including kinetic isotope effect analysis by kinetic isotopically sensitive branching and detecting the presence of protein-based intermediates by tandem-mass based protein sequencing.

Application of mass spectrometry in the mechanistic characterization of key enzymes in ergothioneine and ovothiol biosynthesis

256th National Meeting (2018)

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