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Chemical Compound Review:

AG-E-93142 2-chlorohexa-2,4-dienedioic acid

Synonyms: CTK1A2690, CTK1H0604, CTK2G7598, AC1L49GA, 28823-37-2, ...

Moiseeva, O.V. et al., Vollmer, M.D. et al., Ogawa, N. et al., Skiba, A. et al.

Ogawa, McFall, Klem, Miyashita, Chakrabarty,

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Disease relevance of C03572

The conversion of 2-chloro-cis,cis-muconate by muconate cycloisomerase from Pseudomonas putida PRS2000 yielded two products which by nuclear magnetic resonance spectroscopy were identified as 2-chloro- and 5-chloromuconolactone [1].

High impact information on C03572

Formation of protoanemonin from 2-chloro-cis,cis-muconate by the combined action of muconate cycloisomerase and muconolactone isomerase [2].
UV overlay spectra as well as high-pressure liquid chromatography analyses confirmed that 2-chloro-cis,cis-muconate is transformed by ClcB2 to 5-chloromuconolactone, which during turnover by ClcF gives cis-dienelactone as the sole product. cis-Dienelactone was further hydrolyzed by ClcD2 to maleylacetate [3].
In vitro transcription assays confirmed that 2-chloro-cis,cis-muconate (2-CM) and cis, cis-muconate (CCM), intermediate products from 3-chlorocatechol and catechol, respectively, were inducers of this operon [4].

References

Inability of muconate cycloisomerases to cause dehalogenation during conversion of 2-chloro-cis,cis-muconate. Vollmer, M.D., Fischer, P., Knackmuss, H.J., Schlömann, M. J. Bacteriol. (1994) [Pubmed]
Formation of protoanemonin from 2-chloro-cis,cis-muconate by the combined action of muconate cycloisomerase and muconolactone isomerase. Skiba, A., Hecht, V., Pieper, D.H. J. Bacteriol. (2002) [Pubmed]
A new modified ortho cleavage pathway of 3-chlorocatechol degradation by Rhodococcus opacus 1CP: genetic and biochemical evidence. Moiseeva, O.V., Solyanikova, I.P., Kaschabek, S.R., Gröning, J., Thiel, M., Golovleva, L.A., Schlömann, M. J. Bacteriol. (2002) [Pubmed]
Transcriptional activation of the chlorocatechol degradative genes of Ralstonia eutropha NH9. Ogawa, N., McFall, S.M., Klem, T.J., Miyashita, K., Chakrabarty, A.M. J. Bacteriol. (1999) [Pubmed]

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