5-chloromuconolactone has been researched along with maleoylacetic-acid* in 1 studies
1 other study(ies) available for 5-chloromuconolactone and maleoylacetic-acid
Article | Year |
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Metabolism of 5-chlorosubstituted muconolactones.
The stereochemistry of the four stereoforms of 5-chloro-3-methylmuconolactones could be deduced from NMR and stability data, and from the comparison with authentic (4R, 5S)-5-chloromuconolactone. Muconolactone isomerase of Alcaligenes eutrophus JMP 134 was shown to catalyze syn-elimination of hydrogen chloride from (4R, 5R)-5-chloro-3-methylmuconolactone, (4R, 5S)-5-chloro-3 -methylmuconolactone and (4R, 5S)-5-chloromuconolactone to form 3-methyl-trans-dienelactone, 3-methyl-cis-dienelactone and a 3:1 mixture of cis- and trans-dienelactone, respectively. 3-Methyl-trans-dienelactone was a substrate of pJP4-encoded dienelactone hydrolase of A. eutrophus JMP 134, whereas 3-methyl-cis-dienelactone transformation was negligible indicating a restricted substrate specificity of this enzyme. Both substrates were transformed into 3-methylmaleylacetate which in turn was a substrate for maleylacetate reductase. This compound was shown to possess a cyclic structure (4-hydroxy-3-methyl-muconolactone) under acidic conditions. Topics: 4-Butyrolactone; Alcaligenes; Bacterial Proteins; Biotransformation; Carbon-Carbon Double Bond Isomerases; Carboxylic Ester Hydrolases; Isomerases; Maleates; Molecular Structure; Stereoisomerism; Substrate Specificity | 1996 |