Metabolites and dead-end products from the microbial oxidation of quaternary ammonium alcohols

Biodegradation

Volumn 16, Issue 5, 2005, Pages 461-473

  Kaech, Andres ^a   Hofer, Martina ^a   Rentsch, Daniel ^b   Schnider, Christian ^c   Egli, Thomas ^a  

^a SWISS FEDERAL INSTITUTE OF AQUATIC SCIENCE AND TECHNOLOGY   (Switzerland)

^b SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Biodegradation; Cationic surfactants; Electrophoresis mass spectrometry; NMR; Oxidoreductase

Indexed keywords

AMMONIUM COMPOUNDS; BACTERIA; CARBOXYLIC ACIDS; CELLS; ELECTROPHORESIS; HYDROLYSIS; METABOLITES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; STRAIN; SURFACE ACTIVE AGENTS;

CHOLINE; DEAD-END PRODUCTS; ELECTRON ACCEPTORS; ESTERQUAT SURFACTANTS;

ALCOHOLS;

2,3 DIHYDROXYPROPYLTRIMETHYL AMMONIUM; ACETAL DERIVATIVE; ALDEHYDE; CARBON; CARBOXYLIC ACID; CHOLINE; METHYLTRIETHANOL AMMONIUM; NITROGEN; OXYGEN; PHENAZINE METHOSULFATE; QUATERNARY AMMONIUM DERIVATIVE; UNCLASSIFIED DRUG;

BACTERIUM; BIODEGRADATION; OXIDATION;

ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; CAPILLARY ELECTROPHORESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CELL FREE SYSTEM; CONTROLLED STUDY; CYCLIZATION; ELECTRON; ENERGY; ENZYME MECHANISM; METABOLITE; MICROBIAL DEGRADATION; NITROGEN NUCLEAR MAGNETIC RESONANCE; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE;

BACTERIA; BIODEGRADATION, ENVIRONMENTAL; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; QUATERNARY AMMONIUM COMPOUNDS; SURFACE-ACTIVE AGENTS;

BACTERIA (MICROORGANISMS);

EID: 14944342410     PISSN: 09239820     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10532-004-5164-5     Document Type: Article

References (25)

1. AJ Bater WA Venables 1977 The characterization of inducible dehydrogenases specific for the oxidation of d -alanine, allohydroxy-d-proline, choline and sarcosine as peripheral membrane proteins in Pseudomonas aeruginosa Biochim. Biophys. Acta 468 209 226
2. A Bax 1985 A spatially selective composite 90 degrees radiofrequency pulse J. Magn. Reson. 65 142 145
3. A Bax RH Griffey BL Hawkins 1983 Correlation of proton and N-15 chemical-shifts by multiple quantum NMR J. Magn. Reson. 55 301 315
4. AL Davis J Keeler ED Laue D Moskau 1992 Experiments for recording pure-absorption heteronuclear correlation spectra using pulsed field gradients J. Magn. Reson. 98 207 216
5. DB Dess JC Martin 1983 Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones J. Org. Chem. 48 4155 4156
6. PE Hellberg K Bergstroem K Holmberg 2000 Cleavable surfactants J. Surf. Det. 3 81 91
7. S Ikuta K Matuura S Imamura H Misaki Y Horiuti 1977 Oxidative pathway of choline to betaine in the soluble fraction prepared from Arthrobacter globiformis J. Biochem. (Tokyo) 82 157 163
8. J Jeener BH Meier P Bachman RR Ernst 1979 Investigation of exchange processes by two-dimensional NMR spectroscopy J. Chem. Phys. 71 4546 4553
9. Kaech (2002) Microbial degradation of quaternary ammonium alcohols - hydrolysis products of esterquat surfactants used as fabric softeners. Diss. ETH Nr. 14757. Swiss Federal Institute of Technology, Zurich
10. J Koolman KH Röhm 1998 Taschenatlas der Biochemie. Georg Thieme Verlag Stuttgart New York
11. GJJ Kortstee 1970 The aerobic decomposition of choline by microorganisms Arch. Microbiol. 71 235 244
12. G Krueger D Boltersdorf K Overkempe 1998 Esterquats K Holmberg Novel Surfactants Marcel Dekker New York 116 139
13. D Lamark I Kaasen MW Eshoo P Falkenberg J McDougall AR Strom 1991 DNA sequence and analysis of the bet genes encoding the osmoregulatory choline-glycine betaine pathway of Escherichia coli Mol. Microbiol. 5 1049 1064
14. T Nagasawa N Mori Y Tani K Ogata 1976 Characerization of choline dehydrogenase from Pseudomonas aeruginosa A-16 Agric. Biol. Chem. 40 2077 2084
15. A Ogawa DP Curran 1997 Benzotrifluorid: A useful alternative solvent for organic reactions currently conducted in dichloromethane and related solvents J. Org. Chem. 62 450 451
16. M Ohta-Fukuyama Y Miyake S Emi T Yamano 1980 Identification and properties of the prosthetic group of choline oxidase from Alcaligenes sp J. Biochem. (Tokyo) 88 197 203
17. AG Palmer J Cavanagh PE Wright M Rance 1991 Sensitivity improvement in proton-detected 2-dimensional heteronuclear correlation NMR-spectroscopy J. Magn. Reson. 93 515 170
18. N Pfennig F Widdel HG Trueper 1981 The dissimilatory sulfate-reducing bacteria MP Starr H Stolp HG Trueper A Balows HG Schlegel The Prokaryotes Springer Verlag Berlin 931 Vol I
19. R Puchta P Krings P Sandkühler 1993 A new generation of softeners Tenside Surfact Det. 30 186 191
20. R Russell RK Scopes 1994 Use of hydrophobic chromatography for purification of the membrane-located choline dehydrogenase from a Pseudomonas strain Bioseparation 4 279 284
21. AJ Shaka PB Barker R Freeman 1985 Computer-optimized decoupling scheme for wideband applications and low-level operation J. Magn. Reson. 64 547 552
22. AJ Shaka J Keeler T Frenkiel R Freeman 1983 An improved sequence for broadband decoupling: WALTZ-16 J. Magn. Reson. 52 335 338
23. JR Simms DA Woods DR Walley T Keough BS Schwab RJ Larson 1992 Integrated approach to surfactant environmental safety assessment: fast atom bombardment mass spectrometry and liquid scintillation counting to determine the mechanism and kinetics of surfactant biodegradation Anal. Chem. 64 2951 2957
24. J Waters KS Lee V Perchard M Flanagan P Clarke 2000 Monitoring of diester cationic surfactant residues in UK and Dutch sewage treatment effluents Tenside Surf. Det. 37 161 171
25. W Wilker D Leibfritz R Kerssebaum W Bermel 1993 Gradient selection in inverse heteronuclear correlation spectroscopy J. Magn. Reson. 78 287 292