The syntheses of the following organomercurials are described: 2-chloromercuri-4-nitrophenol, 2-chloromercuri-4,6-dinitrophenol, 4-chloromercuri-2-nitrophenol and 2,6-dichloromercuri-4-nitrophenol. All four organomercurials show large spectral changes in the visible spectrum when thiols displace a more weakly bound ligand such as EDTA from the mercury atom. These spectral changes are primarily associated with pK perturbation of the nitrophenols. The mercurials are therefore chromophoric probes for thiol groups in proteins and other thiols of biological interest. The enzyme d-glyceraldehyde 3-phosphate dehydrogenase from lobster muscle is used as a model system in which the properties of the organomercurials may be illustrated. In particular it is shown how d-glyceraldehyde 3-phosphate dehydrogenase carboxymethylated at the active site may be mercurated at a specific site. This mercurial derivative may be crystallized and shown to be isomorphous with the parent enzyme. The mercurials also act as ‘reporter groups’ by monitoring phosphate or pyrophosphate binding to the enzyme. The mercurials may also be used to estimate cations by an EDTA displacement method.
A new class of chromophoric organomercurials and their reactions with d-glyceraldehyde 3-phosphate dehydrogenase
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C. H. McMurray, D. R. Trentham; A new class of chromophoric organomercurials and their reactions with d-glyceraldehyde 3-phosphate dehydrogenase. Biochem J 1 December 1969; 115 (5): 913–921. doi: https://doi.org/10.1042/bj1150913
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