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Investigation of the Mechanism of Action of Pyrogallol–Phloroglucinol Transhydroxylase by Using Putative Intermediates
Author(s) -
Paizs Csaba,
BartlewskiHof Ulrike,
Rétey János
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601053
Subject(s) - phloroglucinol , pyrogallol , mechanism (biology) , chemistry , mechanism of action , biochemistry , organic chemistry , physics , in vitro , quantum mechanics
Pyrogallol–phloroglucinol transhydroxylase from Pelobacter acidigallici , a molybdopterin‐containing enzyme, catalyzes a key reaction in the anaerobic degradation of aromatic compounds. In vitro, the enzymatic reaction requires 1,2,3,5‐tetrahydroxybenzene as a cocatalyst and the transhydroxylation occurs without exchange with hydroxy groups from water. To test our previous proposal that the transfer of the hydroxy group occurs via 2,4,6,3′,4′,5′‐hexahydroxydiphenyl ether as an intermediate, we synthesized this compound and investigated its properties. We also describe the synthesis and characterization of 3,4,5,3′,4′,5′‐hexahydroxydiphenyl ether. Both compounds could substitute for the cocatalyst in vitro. This indicates that the diphenyl ethers can intrude into the active site and initiate the catalytic cycle. Recently, the X‐ray crystal structure of the transhydroxylase (TH) was published16 and it supports the proposed mechanism of hydroxy‐group transfer.