Production of trimethylamine from structurally related trimethylammonium compounds by resting cell suspensions of γ-butyrobetaine- and D,l-carnitine-grown Acinetobacter calcoaceticus and Pseudomonas putida

Sasha Englard, John S. Blanchard, Judy Miura-Fraboni

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The degradation of trimethylammonium compounds that are structurally related to γ-butyrobetaine and D,l-carnitine has been examined with variously grown resting cell suspensions of Acinetobacter calcoaceticus and Pseudomonas putida. Ac. calcoaceticus grown on either γ-butyrobetaine effectively degraded D,l-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 γ-butyrobetaine or D,l-carnitine as sole source of carbon degraded any of the following quaternary ammonium compounds: glycinebetaine, N-trimethylethanolamine-O-phosphate, N-trimethylethanolamine-O-sulfate, 3-N-trimethylaminopropanol, 3-N-trimethylaminopropionitrile, 3-N-trimethylaminopropionic 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 Hofmann-type of elimination reaction.

Original languageEnglish (US)
Pages (from-to)305-310
Number of pages6
JournalArchives of Microbiology
Volume135
Issue number4
DOIs
StatePublished - Sep 1983

Fingerprint

Acinetobacter calcoaceticus
Pseudomonas putida
Carnitine
Suspensions
Acids
Betaine
Carbon
Quaternary Ammonium Compounds
Degradation
Sulfonic Acids
Sulfates
trimethylamine
gamma-butyrobetaine
Phosphates

Keywords

  • γ-Butyrobetaine
  • 5-N-Trimethylaminopentanoic acid
  • Acinetobacter calcoaceticus
  • D,l-3-Fluoro-4-N-trimethylaminobutyric acid
  • D,l-4-N-Trimethylaminocrotonic acid
  • D- and L-Carnitine
  • Pseudomonas putida
  • Trimethylamine
  • Trimethylammonium compounds

ASJC Scopus subject areas

  • Microbiology

Cite this

@article{23ab2ee4256f42b98d1c3a5c6f9aebe3,
title = "Production of trimethylamine from structurally related trimethylammonium compounds by resting cell suspensions of γ-butyrobetaine- and D,l-carnitine-grown Acinetobacter calcoaceticus and Pseudomonas putida",
abstract = "The degradation of trimethylammonium compounds that are structurally related to γ-butyrobetaine and D,l-carnitine has been examined with variously grown resting cell suspensions of Acinetobacter calcoaceticus and Pseudomonas putida. Ac. calcoaceticus grown on either γ-butyrobetaine effectively degraded D,l-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 γ-butyrobetaine or D,l-carnitine as sole source of carbon degraded any of the following quaternary ammonium compounds: glycinebetaine, N-trimethylethanolamine-O-phosphate, N-trimethylethanolamine-O-sulfate, 3-N-trimethylaminopropanol, 3-N-trimethylaminopropionitrile, 3-N-trimethylaminopropionic 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 Hofmann-type of elimination reaction.",
keywords = "γ-Butyrobetaine, 5-N-Trimethylaminopentanoic acid, Acinetobacter calcoaceticus, D,l-3-Fluoro-4-N-trimethylaminobutyric acid, D,l-4-N-Trimethylaminocrotonic acid, D- and L-Carnitine, Pseudomonas putida, Trimethylamine, Trimethylammonium compounds",
author = "Sasha Englard and Blanchard, {John S.} and Judy Miura-Fraboni",
year = "1983",
month = "9",
doi = "10.1007/BF00413486",
language = "English (US)",
volume = "135",
pages = "305--310",
journal = "Archives of Microbiology",
issn = "0302-8933",
publisher = "Springer Verlag",
number = "4",

}

TY - JOUR

T1 - Production of trimethylamine from structurally related trimethylammonium compounds by resting cell suspensions of γ-butyrobetaine- and D,l-carnitine-grown Acinetobacter calcoaceticus and Pseudomonas putida

AU - Englard, Sasha

AU - Blanchard, John S.

AU - Miura-Fraboni, Judy

PY - 1983/9

Y1 - 1983/9

N2 - The degradation of trimethylammonium compounds that are structurally related to γ-butyrobetaine and D,l-carnitine has been examined with variously grown resting cell suspensions of Acinetobacter calcoaceticus and Pseudomonas putida. Ac. calcoaceticus grown on either γ-butyrobetaine effectively degraded D,l-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 γ-butyrobetaine or D,l-carnitine as sole source of carbon degraded any of the following quaternary ammonium compounds: glycinebetaine, N-trimethylethanolamine-O-phosphate, N-trimethylethanolamine-O-sulfate, 3-N-trimethylaminopropanol, 3-N-trimethylaminopropionitrile, 3-N-trimethylaminopropionic 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 Hofmann-type of elimination reaction.

AB - The degradation of trimethylammonium compounds that are structurally related to γ-butyrobetaine and D,l-carnitine has been examined with variously grown resting cell suspensions of Acinetobacter calcoaceticus and Pseudomonas putida. Ac. calcoaceticus grown on either γ-butyrobetaine effectively degraded D,l-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 γ-butyrobetaine or D,l-carnitine as sole source of carbon degraded any of the following quaternary ammonium compounds: glycinebetaine, N-trimethylethanolamine-O-phosphate, N-trimethylethanolamine-O-sulfate, 3-N-trimethylaminopropanol, 3-N-trimethylaminopropionitrile, 3-N-trimethylaminopropionic 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 Hofmann-type of elimination reaction.

KW - γ-Butyrobetaine

KW - 5-N-Trimethylaminopentanoic acid

KW - Acinetobacter calcoaceticus

KW - D,l-3-Fluoro-4-N-trimethylaminobutyric acid

KW - D,l-4-N-Trimethylaminocrotonic acid

KW - D- and L-Carnitine

KW - Pseudomonas putida

KW - Trimethylamine

KW - Trimethylammonium compounds

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U2 - 10.1007/BF00413486

DO - 10.1007/BF00413486

M3 - Article

AN - SCOPUS:0021071812

VL - 135

SP - 305

EP - 310

JO - Archives of Microbiology

JF - Archives of Microbiology

SN - 0302-8933

IS - 4

ER -