@article{mbs:/content/journal/micro/10.1099/00221287-18-3-733, author = "Webley, D. M. and Duff, R. B. and Farmer, V. C.", title = "The Influence of Chemical Structure on β-oxidation by Soil Nocardias", journal= "Microbiology", year = "1958", volume = "18", number = "3", pages = "733-746", doi = "https://doi.org/10.1099/00221287-18-3-733", url = "https://www.microbiologyresearch.org/content/journal/micro/10.1099/00221287-18-3-733", publisher = "Microbiology Society", issn = "1465-2080", type = "Journal Article", abstract = "Summary: Studies of the β-oxidation of the fatty acid side-chain of certain ω-aryl- and ω -aryloxy-n-alkylcarboxylic acids by Nocardia opaca (strain T16) and Nocardia sp. (strain P2) show that y-phenylbutyric is more rapidly oxidized than y-phenoxy- butyric acid. The effect of the oxygen bridge is even more striking when γ-(1-naphthyl)- and γ -(1-naphthyloxy)-butyric acids are compared. The rate of β -oxidation (by strain T18) of 3-, 4-, and 2-isomers decreases in that order. This applies to mono-chloro- and monomethylphenoxybutyric acids and to monochlorophenoxypropionic acids. Substitution in position 2 has by far the greatest effect and chlorine exerts a bigger influence than a methyl group in all positions. The conversion of γ-(2-methyl- 4-chlorophenoxy)-butyric acid (MCPB) and γ -(2:4-dichlorophenoxy)-butyric acid (2:4-DB) is very slow and proceeds only to β-hydroxy acids. On the other hand, ϵ-(2-methyl-4-chlorophenoxy)-, ϵ -(2:4-dichlorophenoxy)- and ϵ -(2-chlorophenoxy)-caproic acids are relatively rapidly converted to their corresponding butyric acid derivatives. With strain T16 ω-(2-naphthyloxy)-butyric and propionic acids are more rapidly converted to their corresponding acetic acids and phenols respectively than the ω-(1-naphthyloxy) compounds. The rate of β-oxidation of γ-phenyl-, γ-(3-indolyl)- and γ -(1-naphthyl)- butyric acids (by strain P2) decreases in that order. It has been shown that β-hydroxy acid intermediates are formed from ω-aryloxybutyric acids and those from MCPB, γ-(2-methyl-4-chlorophenoxy)-crotonic and γ-(2-naphthyl-oxy)-butyric acids have been isolated and identified.", }