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Production of trimethylamine from structurally related trimethylammonium compounds by resting cell suspensions of γ-butyrobetaine- andD,l-carnitine-grownAcinetobacter calcoaceticusandPseudomonas putida

✍ Scribed by Sasha Englard; John S. Blanchard; Judy Miura-Fraboni


Book ID
104764304
Publisher
Springer
Year
1983
Tongue
English
Weight
763 KB
Volume
135
Category
Article
ISSN
0302-8933

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✦ Synopsis


The degradation of trimethylammonium compounds that are structurally related to y-butyrobetaine and D,L-carnitine has been examined with variously grown resting cell suspensions of Acinetobacter calcoaeeticus and Pseudomonas putida. Ac. calcoaceticus grown on either 7-butyrobetaine effectively degraded o,I~-3-fluoro-4 N-trimethylaminobutyric, 4-N-trimethylaminocrotonic and 5-N-trimethylaminopentanoic acids with stoichiometric formation of triylaminopentanoic acids with stoichiometric formation of trimethylamine. None of these betaine analogs was metabolized by Ps. putida grown on D,L-carnitine as sole source of carbon. Only D,L-carnitine-grown Ac. calcoaceticus showed a slow but significant utilization of D,L-3-chloro-4-N-trimethylaminobutyric acid with equivalent formation of trimethylamine. Neither Ac. calcoaceticus nor Ps. putida, grown on either 7-butyrobetaine or D,L-carnitine as sole source of carbon degraded any of the following quaternary ammonium compounds: glycinebetaine, N-trimethylethanolamine-Ophosphate, N-trimethylett~anolamine-O-sulfate, 3-N-trimethylaminopropanol, 3-N-trimethylaminopropionitrile, 3-Ntrimethylaminopropionic acid, 3-N-trimethylaminopropane sulfonic acid and 6-N-trimethylaminohexanoic acid. Cleavage of the C-N bond of 4-N-trimethylaminocrotonic acid, and lack of stereochemical specificity with respect to the configuration at C-3 for the other betaines undergoing a similar degradation with formation of trimethylamine, are inconsistent with a mechanism involving a simple Hofmanntype of elimination reaction.


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Assimilation of γ-butyrobetaine, andd-an
✍ Judy Miura-Fraboni; Hans-Peter Kleber; Sasha Englard 📂 Article 📅 1982 🏛 Springer 🌐 English ⚖ 668 KB

The metabolic pattern of utilization of [1,2,3,4-14C, methyl-3H] 7-butyrobetaine and D-and L-[1-14C, methyl-3H]carnitine has been examined with variously grown resting cell suspensions of Acinetobacter calcoaceticus and Pseudomonas putida. Ps. putida grown on D,L-carnitine as the sole source of carb