2-Hydroxyisocaproyl-CoA dehydratase and its activator from Clostridium difficile

FEBS Journal

Volumn 272, Issue 2, 2005, Pages 550-561

  Kim, Jihoe ^a   Darley, Daniel ^a   Buckel, Wolfgang ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

ATP; Electron recycling; Iron sulfur; Leucine fermentation; Radical mechanism

Indexed keywords

2 HYDROXYISOCAPROYL COENZYME A DEHYDRATASE; 2 HYDROXYISOCAPROYL COENZYME A DEHYDRATASE ACTIVATOR; ADENOSINE TRIPHOSPHATE; COENZYME A; DITHIOERYTHRITOL; DITHIONITE; ENZYME ACTIVATOR; HYDROLYASE; IRON; ISOCAPRENOYL COENZYME A; LEUCINE; MAGNESIUM CHLORIDE; METAL ION; MOLYBDENUM; NITROGENASE; SULFUR; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CATALYSIS; CLOSTRIDIUM DIFFICILE; DEHYDRATION; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INACTIVATION; FERMENTATION; GENE; HADBC GENE; HADI GENE; HYDROLYSIS; NONHUMAN; NUCLEOTIDE SEQUENCE; OBSERVATION; PRIORITY JOURNAL; STOICHIOMETRY;

3-HYDROXYACYL COA DEHYDROGENASES; ADENOSINE TRIPHOSPHATASES; CLONING, MOLECULAR; CLOSTRIDIUM DIFFICILE; ENZYME ACTIVATION; FERMENTATION; LEUCINE;

CLOSTRIDIUM; CLOSTRIDIUM DIFFICILE; ESCHERICHIA COLI; POSIBACTERIA;

EID: 12544251513     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2004.04498.x     Document Type: Article

References (48)

1. Kim J, Hetzel M, Boiangiu CD & Buckel W (2004) Dehydration of (R)-2-hydroxyacyl-CoA to enoyl-CoA in the fermentation of alpha-amino acids by anaerobic bacteria. FEMS Microbiol Rev 28, 455-468.
2. Buckel W (2001) Unusual enzymes involved in five pathways of glutamate fermentation. Appl Microbiol Biotechnol 57, 263-273.
3. Hans M, Bill E, Cirpus I, Pierik AJ, Hetzel M, Alber D & Buckel W (2002) Adenosine triphosphate-induced electron transfer in 2-hydroxyglutaryl-CoA dehydratase from Acidaminococcus fermentans. Biochemistry 41, 5873-5882.
4. Buckel W, Hetzel M & Kim J (2004) ATP-driven electron transfer in enzymatic radical reactions. Curr Opin Chem Biol 8, 462-467.
5. Locher KP, Hans M, Yeh AP, Schmid B, Buckel W & Rees DC (2001) Crystal structure of the Acidaminococcus fermentans 2-hydroxyglutaryl-CoA dehydratase component A. J Mol Biol 307, 297-308.
6. Tamannaei A (2003) Untersuchungen zum Katalysemechnismus der 2-Hydroxyglutaryl-CoA-Dehydratase aus Fusobacterium nucleatum, Diploma Thesis, Philipps-Universität Marburg, Germany.
7. Hans M, Buckel W & Bill E (2000) The iron-sulfur clusters in 2-hydroxyglutaryl-CoA dehydratase from Acidaminococcus fermentans: biochemical and spectroscopic investigations. Eur J Biochem 267, 7082-7093.
8. Klees AG, Linder D & Buckel W (1992) 2-Hydroxyglutaryl-CoA dehydratase from Fusobacterium nucleatum (subsp. nucleatum): an iron-sulfur flavoprotein. Arch Microbiol 158, 294-301.
9. Hans M, Sievers J, Müller U, Bill E, Vorholt JA, Linder D & Buckel W (1999) 2-Hydroxyglutaryl-CoA dehydratase from Clostridium symbiosum. Eur J Biochem 265, 404-414.
10. Kapatral V, Anderson I, Ivanova N, Reznik G, Los T, Lykidis A, Bhattacharyya A, Bartman A, Gardner W, Grechkin G, Zhu L, Vasieva O, Chu L, Kogan Y, Chaga O, Goltsman E, Bernal A, Larsen N, D'Souza M, Walunas T, Pusch G, Haselkorn R, Fonstein M, Kyrpides N & Overbeek R (2002) Genome sequence and analysis of the oral bacterium Fusobacterium nucleatum strain ATCC 25586. J Bacteriol 184, 2005-2018.
11. Kuchta RD & Abeles RH (1985) Lactate reduction in Clostridium propionicum: purification and properties of lactyl-CoA dehydratase. J Biol Chem 260, 13181-13189.
12. Kuchta RD, Hanson GR, Holmquist B & Abeles RH (1986) Fe-S centers in lactyl-CoA dehydratase. Biochemistry 25, 7301-7307.
13. Dickert S, Pierik AJ, Linder D & Buckel W (2000) The involvement of coenzyme A esters in the dehydration of (R)-phenyllactate to (E)-cinnamate by Clostridium sporogenes. Eur J Biochem 267, 3874-3884.
14. Dickert S, Pierik AJ & Buckel W (2002) Molecular characterization of phenyllactate dehydratase and its initiator from Clostridium sporogenes. Mol Microbiol 44, 49-60.
15. Bader J, Rauschenbach P & Simon H (1982) On a hitherto unknown fermentation path of several amino acids by proteolytic clostridia. FEBS Lett 140, 67-72.
16. Elsden SR & Hilton MG (1978) Volatile acid production from threonine, valine, leucine and isoleucine by clostridia. Arch Microbiol 117, 165-172.
17. Britz ML & Wilkinson RG (1982) Leucine dissimilation to isovaleric and isocaproic acids by cell suspensions of amino acid fermenting anaerobes: the Stickland reaction revisited. Can J Microbiol 28, 291-300.
18. Thauer RK, Jungermann K & Decker K (1977) Energy conservation in chemotrophic anaerobic bacteria. Bacteriol Rev 41, 100-180.
19. Shultzaberger RK, Bucheimer RE, Rudd KE & Schneider TD (2001) Anatomy of Escherichia coli ribosome binding sites. J Mol Biol 313, 215-228.
20. Stoddart B & Wilcox MH (2002) Clostridium difficile. Curr Opin Infect Dis 15, 513-518.
21. Müller U & Buckel W (1995) Activation of (R)-2-hydroxyglutaryl- CoA dehydratase from Acidaminococcus fermentans. Eur J Biochem 230, 698-704.
22. Buckel W (1980) The reversible dehydration of (R)-2-hydroxyglutarate to (E)-glutaconate. Eur J Biochem 106, 439-447.
23. Brunelle SL & Abeles RH (1993) The stereochemistry of hydration of acrylyl-CoA catalyzed by lactyl-CoA dehydratase. Bioorganic Chem 21, 118-126.
24. Pitsch C & Simon H (1982) The stereochemical course of the water elimination from (2R)-phenyllactate in the amino acid fermentation of Clostridium sporogenes, Hoppe Seyler's Z. Physiol Chem 363, 1253-1257.
25. Heider J (2001) A new family of CoA-transferases. FEBS Lett 509, 345-349.
26. Kim J (2004) On the enzymatic mechanism of 2-hydroxyisocaproyl-CoA dehydratase from Clostridium difficile, PhD Thesis, Philipps-Universität Marburg, Marburg, Germany.
27. Buckel W (1996) Unusual dehydrations in anaerobic bacteria: considering ketyls (radical anions) as reactive intermediates in enzymatic reactions. FEBS Lett 389, 20-24.
28. Rees DC & Howard JB (2000) Nitrogenase: standing at the crossroads. Curr Opin Chem Biol 4, 559-566.
29. Smith DM, Buckel W & Zipse H (2003) Deprotonation of enoxy radicals: theoretical validation of a 50-year-old mechanistic proposal. Angew Chem Int Ed Engl 42, 1867-1870.
30. Engst S, Vock P, Wang M, Kim JJ & Ghisla S (1999) Mechanism of activation of acyl-CoA substrates by medium chain acyl-CoA dehydrogenase: interaction of the thioester carbonyl with the flavin adenine dinucleotide ribityl side chain. Biochemistry 38, 257-267.
31. Buckel W (1986) Biotin-dependent decarboxylases as bacterial sodium pumps: purification and reconstitution of glutaconyl-CoA decarboxylase from Acidaminococcus fermentans. Methods Enzymol 125, 547-558.
32. Anderson RL & Wood WA (1969) Carbohydrate metabolism in microorganisms. Annu Rev Microbiol 23, 539-578.
33. Tang KH, Chang CH & Frey PA (2001) Electron transfer in the substrate-dependent suicide inactivation of lysine 5,6-aminomutase. Biochemistry 40, 5190-5199.
34. Frazzon J & Dean DR (2003) Formation of iron-sulfur clusters in bacteria: an emerging field in bioinorganic chemistry. Curr Opin Chem Biol 7, 166-173.
35. Wächtershäuser G (1992) Groundworks for an evolutionary biochemistry: the iron-sulphur world. Prog Biophys Mol Biol 58, 85-201.
36. 15N-labelled chiral Boc-amino acids from triflates: enantiomers of leucine and phenylalanine. J Chem Soc, Perkin Trans 1, 11-14.
37. Gibson TW & Erman WF (1972) The photochemistry of substituted 1,5-hexadien-3-ones. J Org Chem 37, 1148-1154.
38. Kawaguchi A, Yoshimura T & Okuda S (1981) A new method for the preparation of acyl-CoA thioesters. J Biochem (Tokyo) 89, 337-339.
39. Sambrook J & Russell DW (2001) Molecular Cloning: a Laboratory Manual, 3rd edn. Cold Spring. Harbor Laboratory Press, Cold Spring Harbor, NY.
40. Selmer T & Andrei PI (2001) p-Hydroxyphenylacetate decarboxylase from Clostridium difficile: a novel glycyl radical enzyme catalysing the formation of p-cresol. Eur J Biochem 268, 1363-1372.
41. Karasawa T, Ikoma S, Yamakawa K & Nakamura S (1995) A defined growth medium for Clostridium difficile. Microbiology 141, 371-375.
42. Jaworek D & Welsch J (1985) Adenosine 5′-diphosphate and adenosine 5′-monophosphate. Methods of Enzymatic Analysis (Bergmeyer HU, ed.), pp. 365-370. VCH-Verlagsgesellschaft, Weinheim, Germany.
43. Ziegenhorn J, Senn M & Bücher T (1976) Molar absorptivities of beta-NADH and beta-NADPH. Clin Chem 22, 151-160.
44. Selmer T & Buckel W (1999) Oxygen exchange between acetate and the catalytic glutamate residue in glutaconate CoA-transferase from Acidaminococcus fermentans. Implications for the mechanism of CoA-ester hydrolysis. J Biol Chem 274, 20772-20778.
45. 12-containing 2-methyleneglutarate mutase from Clostridium barkeri by high-performance liquid chromatography. J Chromatogr 587, 93-99.
46. Fish WW (1988) Rapid colorimetric micromethod for the quantitation of complexed iron in biological samples. Methods Enzymol 158, 357-364.
47. Cline JD (1969) Spectrophotometric determination of hydrogen sulfide in natural waters. Limnol Oceanogr 14, 454-458.
48. Eikmanns U & Buckel W (1991) Crystalline green 5-hydroxyvaleryl-CoA dehydratase from Clostridium aminovalericum. Eur J Biochem 197, 661-668.