In situ proton NMR analysis of α-alkynoate biotransformations: From 'invisible' substrates to detectable metabolites

European Journal of Biochemistry

Volumn 270, Issue 7, 2003, Pages 1393-1398

  Brecker, Lothar ^a,b   Petschnigg, Julia ^a   Depiné, Nicole ^a   Weber, Hansjörg ^a   Ribbons, Douglas W ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

2 Butynedioate; in situ 1H NMR; Propynoate; Pseudomonas putida; Triple bond

Indexed keywords

2 BUTYNEDIOATE; 2 KETOBUTANDIOATE; 3 HYDROXYPROPANOATE; 3 KEOPROPANOATE; ACETALDEHYDE; ACETIC ACID; BUTANE; FORMIC ACID; LACTIC ACID; PROPANE; PROPYNOATE; PYRUVIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GROWTH; BIODEGRADATION; BIOTRANSFORMATION; CHEMICAL BOND; DECARBOXYLATION; HYDRATION; HYDROLYSIS; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS PUTIDA;

ACETALDEHYDE; ACETIC ACID; ALKYNES; BIOTRANSFORMATION; CELL DIVISION; FATTY ACIDS, UNSATURATED; KETO ACIDS; LACTIC ACID; MAGNETIC RESONANCE SPECTROSCOPY; PROPIONIC ACIDS; PROTONS; PSEUDOMONAS PUTIDA; PYRUVIC ACID; SPECTROPHOTOMETRY, ULTRAVIOLET;

BACTERIA (MICROORGANISMS); NEGIBACTERIA; PSEUDOMONAS; PSEUDOMONAS PUTIDA;

EID: 0037395295     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1033.2003.03460.x     Document Type: Article

References (19)

1. Beilstein Crossfire, Version 3.1. Database PS0201PR. (1996-2002) Beilstein Information Systems GmbH, Frankfurt, Germany.
2. Benton, P.M.C., Christiansen, J., Dean, D.R. & Seefeldt, L.C. (2001) Stereospecificity of acetylene reduction catalyzed by nitrogenase. J. Am. Chem. Soc. 123, 1822-1827.
3. Rosner, B.M., Rainey, F.A., Kroppenstedt, R.M. & Schink, B. (1997) Acetylene degradation by new isolates of aerobic bacteria and comparison of acetylene hydratase enzymes. FEMS Microbiol. Lett. 148, 175-180.
4. Walsh, C. (1977) Recent developments in suicide substrates and other active site-directed inactivating agents of specific target enzymes. Horizons Biochem. Biophys. 3, 36-81.
5. Marcotte, P. & Walsh, C. (1978) Sequence of reactions which follow enzymic oxidation of propargylglycine. Biochemistry 17, 5613-5619.
6. Miesowicz, F.M. & Bloch, K. (1979) Purification of hog liver isomerase. Mechanism of isomerization of 3-alkenyl and 3-alkynyl thioesters. J. Biol. Chem. 254, 5868-5877.
7. Ahmed, S. (1991) Microbial oxidative reactions of arenes PhD Thesis. Imperial College, London, UK.
8. van den Tweel, W.J.J. & De Bont, J.A.M. (1985) Metabolism of 3-butyn-1-ol by Pseudomonas BB1. J. Gen. Microbiol. 131, 3155-3162.
9. Yamada, E.W. & Jakoby, W.B. (1958) Enzymatic utilization of acetylenic compounds-I. An enzyme converting acetylenedicarboxylic acid to pyruvate. J. Biol. Chem. 233, 706-711.
10. Yamada, E.W. & Jakoby, W.B. (1958) Enzymatic utilization of acetylenic compounds - II. Acetylenemonocarboxylic acid hydrase. J. Biol. Chem. 233, 941-945.
11. Brecker, L. & Ribbons, D.W. (2000) Biotransformations monitored in situ by proton nuclear magnetic resonance spectroscopy. Trends Biotechnol. 18, 197-202.
12. Weber, H. & Brecker, L. (2000) Online NMR for monitoring biocatalysed reactions. Curr. Opin. Biotechnol. 11, 572-578.
13. Gillies, R.J. (1994) NMR in Physiology and Biomedicine. Academic Press, New York.
14. Barbotin, J.N. & Portais, J.C. (2000) NMR in Microbiology. Theory and Applications. Horizon Scientific Press, Wymondham, UK.
15. Field, L.D. & Sternhell, S. (1989) Analytical NMR. John Wiley & Sons, New York, USA.
16. 2O. Microbiology 145, 3389-3397.
17. Morawski, B., Eaton, R.W., Rossiter, J.T., Guoping, S., Griengl, H. & Ribbons, D.W. (1997) 2-Naphthoate catabolic pathway in Burkholderia strain. JT 1500. J. Bacteriol. 179, 115-121.
18. Guéron, M., Plateau, P. & Decorps, M. (1991) Solvent signal suppression in NMR. Prog. NMR Spectrosc. 23, 135-209.
19. Hore, J.P. (1989) Solvent suppression. In Methods in Enzymology (Oppenheimer, N.J. & James, J.T., eds), Vol. 176, pp. 64-77. Academic Press, Inc., San Diego, CA, USA.