ISSN:
1432-072X
Keywords:
2-Chloro-4-methylphenoxyacetic acid
;
2-Chloro-4-methyl-cis,cis-muconate
;
4-Carboxymethy
;
2-chloro-4-methylmuconolactone
;
4-Carboxychloromethyl-3-methylbut-2-en-4-olide
;
Alcaligenes eutrophus JMP 134
;
Ortho-cleavage
;
Cycloisomerization
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
Notes:
Abstract 2-Chloro-4-methylphenoxyacetate is not a growth substrate for Alcaligenes eutrophus JMP 134 and JMP 1341. It is, however, being transformed by enzymes of 2,4-dichlorophenoxyacetic acid metabolism to 2-chloro-4-methyl-cis, cis-muconate, which is converted by enzymatic 1,4-cycloisomerization to 4-carboxymethyl-2-chloro-4-methylmuconolactone as a dead end metabolite. Chemically, only 3,6-cycloisomerization occurs, giving rise to both diastereomers of 4-carboxychloromethyl-3-methylbut-2-en-4-olide. Those lactones harbonring a chlorosubstituent on the 4-carboxymethyl side chain were surprisingly stable under physiological as well as acidic conditions.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00249121
Permalink
