Article ; Online: Evolution of a xenobiotic degradation pathway: formation and capture of the labile phthaloyl-CoA intermediate during anaerobic phthalate degradation.
2018 Volume 108, Issue 6, Page(s) 614–626
Abstract: Xenobiotic phthalates are industrially produced on the annual million ton scale. The oxygen-independent enzymatic reactions involved in anaerobic phthalate degradation have only recently been elucidated. In vitro assays suggested that phthalate is first ... ...
| Abstract | Xenobiotic phthalates are industrially produced on the annual million ton scale. The oxygen-independent enzymatic reactions involved in anaerobic phthalate degradation have only recently been elucidated. In vitro assays suggested that phthalate is first activated to phthaloyl-CoA followed by decarboxylation to benzoyl-CoA. Here, we report the heterologous production and characterization of the enzyme initiating anaerobic phthalate degradation from 'Aromatoleum aromaticum': a highly specific succinyl-CoA:phthalate CoA transferase (SPT, class III CoA transferase). Phthaloyl-CoA formed by SPT accumulated only to sub-micromolar concentrations due to the extreme lability of the product towards intramolecular substitution with a half-life of around 7 min. Upon addition of excess phthaloyl-CoA decarboxylase (PCD), the combined activity of both enzymes was drastically shifted towards physiologically relevant benzoyl-CoA formation. In conclusion, a massive overproduction of PCD in phthalate-grown cells to concentrations >140 μM was observed that allowed for efficient phthaloyl-CoA conversion at concentrations 250-fold below the apparent K |
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| MeSH term(s) | Anaerobiosis ; Bacterial Proteins/genetics ; Bacterial Proteins/metabolism ; Carboxy-Lyases/genetics ; Carboxy-Lyases/metabolism ; Coenzyme A/metabolism ; Kinetics ; Phthalic Acids/chemistry ; Phthalic Acids/metabolism ; Phylogeny ; Rhodocyclaceae/classification ; Rhodocyclaceae/enzymology ; Rhodocyclaceae/genetics ; Rhodocyclaceae/metabolism ; Xenobiotics/metabolism |
| Chemical Substances | Bacterial Proteins ; Phthalic Acids ; Xenobiotics ; phthalic acid (6O7F7IX66E) ; Carboxy-Lyases (EC 4.1.1.-) ; Coenzyme A (SAA04E81UX) |
| Language | English |
| Publishing date | 2018-04-26 |
| Publishing country | England |
| Document type | Journal Article ; Research Support, Non-U.S. Gov't |
| ZDB-ID | 619315-8 |
| ISSN | 1365-2958 ; 0950-382X |
| ISSN (online) | 1365-2958 |
| ISSN | 0950-382X |
| DOI | 10.1111/mmi.13962 |
| Database | MEDical Literature Analysis and Retrieval System OnLINE |
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