An α/β-fold C-C bond hydrolase is involved in a central step of nicotine catabolism by Arthrobacter nicotinovorans

Journal of Bacteriology

Volumn 187, Issue 24, 2005, Pages 8516-8519

  Sachelaru, Paula ^a   Schiltz, Emile ^a   Igloi, Gabor L ^a   Brandsch, Roderich ^a,b  

^a UNIVERSITY OF FREIBURG   (Germany)

^b Institut fur Biochemie und Molekularbiologie   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CARBON; COMPLEMENTARY DNA; HYDROLASE; NICOTINE;

ARTHROBACTER; ARTHROBACTER NICOTINOVORANS; ARTICLE; CATABOLISM; ENZYME ACTIVITY; GENETIC TRANSCRIPTION; GRAM POSITIVE BACTERIUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR CLONING; NONHUMAN; OPEN READING FRAME; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PROTEIN PURIFICATION; SOIL MICROFLORA; TOBACCO;

ALKALOIDS; ARTHROBACTER; BIODEGRADATION, ENVIRONMENTAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CLONING, MOLECULAR; GENE ORDER; HETEROCYCLIC COMPOUNDS; HYDROLASES; NICOTINE; OPEN READING FRAMES; PLASMIDS; PYRIDINES;

ARTHROBACTER; ARTHROBACTER NICOTINOVORANS; BACTERIA (MICROORGANISMS); NICOTIANA TABACUM; POSIBACTERIA;

EID: 28844438670     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/JB.187.24.8516-8519.2005     Document Type: Article

References (20)

1. Ahmad, D., J. Fraser, M. Sylvestre, A. Larose, A. Khan, J. Bergeron, J. M. Juteau, and M. Sondossi. 1995. Sequence of the bphD gene encoding 2-hydroxy-6-oxo-(phenyl/chlorophenyl)hexa-2,4-dienoic acid (HOP/cPDA) hydrolase involved in the biphenyl/polychlorinated biphenyl degradation pathway in Comamonas testosteroni: evidence suggesting involvement of Ser112 in catalytic activity. Gene 156:69-74.
2. Baitsch, D., C. Sandu, and R. Brandsch. 2001. A gene cluster on pAO1 of Arthrobacter nicotinovorans involved in degradation of the plant alkaloid nicotine: cloning, purification, and characterization of 2,6-dihydroxypyridine 3-hydroxylase. J. Bacteriol. 183:5262-5267.
3. Berthold, H., M. Scanarini, C. C. Abney, B. Frorath, and W. Northemann. 1992. Purification of recombinant antigenic epitopes of the human 68-kDa (U1) ribonucleoprotein antigen using the expression system pH6EX3 followed by metal chelating affinity chromatography. Protein Expr. Purif. 3:50-56.
4. Chiribau, C.-B., C. Sandu, M. Fraaije, E. Schiltz, and R. Brandsch. 2004. A novel γ-N-methylaminobutyrate demethylating oxidase involved in catabolism of the tobacco alkaloid nicotine by Arthrobacter nicotinovorans pAO1. Eur. J. Biochem. 271:4677-4684.
5. Decker, K., and H. Bleeg. 1965. Induction and purification of stereospecific nicotine oxidizing enzymes from Arthrobacter oxidans. Biochim. Biophys. Acta 105:313-334.
6. Diaz, E., and K. N. Timmis. 1995. Identification of functional residues in a 2-hydroxymuconic semialdehyde hydrolase. A new member of the alpha/beta hydrolase-fold family of enzymes which cleaves carbon-carbon bonds. J. Biol. Chem. 270:6403-6411.
7. Dunn, G., M. G. Montgomery, F. Mohammed, A. Coker, J. B. Cooper, T. Robertson, J. L. Garcia, T. D. Bugg, and S. P. Wood. 2005. The structure of the C-C bond hydrolase MhpC provides insights into its catalytic mechanism. J. Mol. Biol. 346:253-265.
8. Freudenberg, W., K. König, and J. R. Andreesen. 1988. Nicotine dehydrogenase from Arthrobacter oxidans: a molybdenum-containing hydroxylase. FEMS Microbiol. Lett. 52:13-18.
9. Gherna, R. L., S. H. Richardson, and S. C. Rittenberg. 1965. The bacterial oxidation of nicotine. VI. The metabolism of 2,6- dihydroxypseudooxynicotine. J. Biol. Chem. 240:3669-3674.
10. Gries, F. A., K. Decker, H. Eberwein, and M. Brühmüller. 1961. Über den Abbau des Nicotins durch Bakterienenzyme. VI. Die enzymatische Umwandlung des (γ-Methylamino-propyl)-[6-hydroxy-pyridyl-(3)]-ketons. Biochem. Z. 335:285-302.
11. Hille, R. 1996. The mononuclear molybdenum enzymes. Chem. Rev. 96:2757-2816.
12. Hinkkanen, A., E.-M. Lilius, J. Nowack, R. Maas, and K. Decker. 1983. Purification of the flavoproteins 6-hydroxy-D- and 6-hydroxy-L-nicotine oxidase using hydrophobic affinity chromatography. Hoppe-Seyler's Z. Physiol. Chem. 364:801-806.
13. Holmes, P. E., and S. Rittenberg. 1972. The bacterial oxidation of nicotine. VII. Partial purification and properties of 2,6-dihydroxypyridine oxidase. J. Biol. Chem. 247:7622-7627.
14. Holmquist, M. 2000. Alpha/beta-hydrolase fold enzymes: structures, functions and mechanisms. Curr. Protocol Peptide Sci. 1:209-235.
15. Igloi, G. L., and R. Brandsch. 2003. Sequence of the 165-kilobase catabolic plasmid pAO1 from Arthrobacter nicotinovorans and identification of a pAO1-dependent nicotine uptake system. J. Bacteriol. 185:1976-1986.
16. Li, C., M. G. Montgomery, F. Li, J. J. Mohammed, S. P. Wood, and T. D. Bugg. 2005. Catalytic mechanism of C-C hydrolase MhpC from Escherichia coli: kinetic analysis of His263 and Ser110 site-directed mutants. J. Mol. Biol. 346:241-251.
17. Pokorny, D., L. Brecker, W. Steiner, and D. W. Ribbons. 1999. β-Ketolases-forgotten hydrolytic enzymes? Trends Biotechnol. 15:291-296.
18. Richardson, S. H., and S. C. Rittenberg. 1961. The bacterial oxidation of nicotine. IV. The isolation and identification of 2,6-dihydroxy-N- methylmyosmine. J. Biol. Chem. 236:959-963.
19. Sandu, C., C.-B. Chiribau, and R. Brandsch. 2003. Characterization of HdnoR, the transcriptional repressor of the 6-hydroxy-D-nicotine oxidase gene of Arthrobacter nicotinovorans pAO1, and its DNA-binding activity in response to L- and D-nicotine derivatives. J. Biol. Chem. 278:51307-51315.
20. Schenk, S., A. Hoelz, B. Krauß, and K. Decker. 1998. Gene structure and properties of enzymes of the plasmid-encoded nicotine catabolism of Arthrobacter nicotinovorans. J. Mol. Biol. 284:1322-1339.