Genes encoding acyl-CoA dehydrogenase (AcdH) homologues from Streptomyces coelicolor and Streptomyces avermitilis provide insights into the metabolism of small branched-chain fatty acids and macrolide antibiotic production

Microbiology

Volumn 145, Issue 9, 1999, Pages 2323-2334

  Zhang, Ying Xin ^a   Denoya, Claudio D ^b   Skinner, Deborah D ^b   Fedechko, Ronald W ^b   McArthur, Hamish A I ^b   Morgenstern, Margaret R ^b   Davies, Richard A ^b   Lobo, Sandra ^c   Reynolds, Kevin A ^c   Hutchinson, C Richard ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b PFIZER INC   (United States)

^c VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

Avermectin; Branched chain amino acids; Isotope labelling

Indexed keywords

ACYL COENZYME A; ACYL COENZYME A DEHYDROGENASE; FATTY ACID; ISOBUTYRIC ACID; MACROLIDE; VALINE;

AMINO ACID SEQUENCE; ARTICLE; BACTERIAL GENE; BACTERIAL METABOLISM; BACTERIAL MUTATION; CATABOLISM; ESCHERICHIA COLI; FATTY ACID METABOLISM; MOLECULAR CLONING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEOTIDE SEQUENCE; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; STREPTOMYCES; STREPTOMYCES AVERMITILIS; STREPTOMYCES COELICOLOR;

ESCHERICHIA COLI; STREPTOMYCES AVERMITILIS; STREPTOMYCES COELICOLOR;

EID: 0032884515     PISSN: 13500872     EISSN: None     Source Type: Journal    
DOI: 10.1099/00221287-145-9-2323     Document Type: Article

References (55)

1. Altschul, S. F., Madden, T. L., Schäffer, A. A., Zhang, J., Zhang, Z., Miller, W. & Lipman, D. J. (1997). Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res 25, 3389-3402.
2. Anderson, D. H. & Rodwell, V. W. (1989). Nucleotide sequence and expression in Escherichia coli of the 3-hydroxy-3-methylglutaryl coenzyme A lyase gene of Pseudomonas mevalonii. J Bacteriol 171, 6468-6472.
3. Anzai, H., Kumada, Y., Hara, O., Murakami, T., Itoh, R., Takano, E., Imai, S., Satoh, A. & Nagaoka, K. (1988). Replacement of Streptomyces hygroscopicus genomic segments with in vitro altered DNA sequences. J Antibiot 41, 226-233.
4. Aoyama, T., Ueno, I., Kamijo, T. & Hashimoto, T. (1994). Rat very-long-chain acyl-CoA dehydrogenase, a novel mitochondrial acyl-CoA dehydrogenase gene product, is a rate-limiting enzyme in long-chain fatty acid β-oxidation. cDNA and deduced amino acid sequence and distinct specificities of the cDNA-expressed protein. J Biol Chem 269, 19088-19094.
5. Bibb, M. J., Findlay, P. R. & Johnson, M. W. (1984). The relationship between base composition and codon usage in bacterial genes and its use for the simple and reliable identification of protein coding sequences. Gene 30, 157-166.
6. Bibb, M. J., White, J., Ward, J. M. & Janssen, G. R. (1994). The mRNA for the 23S rRNA methylase encoded by the ermE gene of Saccharopolyspora erythraea is translated in the absence of a conventional ribosome-binding site. Mol Microbiol 14, 533-545.
7. Birch, A. W. & Cullum, J. (1985). Temperature-sensitive mutants of the Streptomyces plasmid pIJ702. J Gen Microbiol 131, 1299-1303.
8. Boynton, Z. L., Bennett, G. N. & Rudolph, F. B. (1996). Cloning, sequencing, and expression of clustered genes encoding β-hydroxybutyryl-coenzyme A (CoA) dehydrogenase, crotonase, and butyryl-CoA dehydrogenase from Clostridium acetobutylicum ATCC 824. J Bacteriol 178, 3015-3024.
9. Bradford, M. M. (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72, 248-254.
10. E-dependent operon subject to catabolite repression during sporulation in Bacillus subtilis. J Bacteriol 178, 4778-4786.
11. Burg, R. W., Miller, B. M., Baker, E. E. & 12 other authors (1979). Avermectins, new family of potent anthelmintic agents: producing organism and fermentation. Antimicrob Agents Chemother 15, 361-367.
12. Denoya, C. D., Trevisan, A. R., Zorzopulos, J., Woloj, M. & Rubeglio, E. (1985). Diversity of plasmid profiles in multiply resistant Klebsiella pneumoniae strains isolated from a single nosocomial environment with a strong antibiotic selection pressure. Microbios Lett 29, 87-93.
13. Denoya, C. D., Skinner, D. D. & Morgenstern, M. R. (1994). A Streptomyces avermitilis gene encoding a 4-hydroxyphenyl-pyruvic acid dioxygenase-like protein that directs the production of homogentisic acid and an ochronotic pigment in Escherichia coli. J Bacteriol 176, 5312-5319.
14. Denoya, C. D., Fedechko, R. W., Hafner, E. W., McArthur, H. A. I., Morgenstern, M. R., Skinner, D. D., Stutzman-Engwall, K., Wax, R. G. & Wernau, W. C. (1995). A second branched-chain α-keto acid dehydrogenase gene cluster (bkdFGH) from Streptomyces avermitilis: its relationship to avermectin biosynthesis and the construction of a bkdF mutant suitable for the production of novel antiparasitic avermectins. J Bacteriol 177, 3504-3511.
15. Denoya, C. D., Skinner, D. D., Fedechko, R. W. & McArthur, H. A. I. (1996). Genetic manipulations of the branched-chain fatty acid supply for the biosynthesis of avermectins in Streptomyces avermitilis. Abstracts of The Sixth Conference on the Genetics and Molecular Biology of Industrial Microorganisms (GMBIM), P60. American Society for Microbiology.
16. Devereux, J., Haeberli, P. & Smithies, O. (1984). A comprehensive set of sequence analysis programs for the VAX. Nucleic Acids Res 12, 387-395.
17. Engel, P. C. (1981). Butyryl-CoA dehydrogenase from Megasphaera elsdenii. Methods Enzymol 71, 359-366.
18. Goodwin, G. W., Rougraff, P. M., Davis, E. J. & Harris, R. A. (1989). Purification and characterization of methylmalonate-semialdehyde dehydrogenase from rat liver: identity to malonate-semialdehyde dehydrogenase. J Biol Chem 264, 14965-14971.
19. Hall, C. L. (1978). Acyl-CoA dehydrogenases and electron transferring flavoprotein. Methods Enzymol 53, 502-518.
20. Han, L. & Reynolds, K. A. (1997). A novel alternate anaplerotic pathway to the glyoxylate cycle in streptomycetes. J Bacteriol 179, 5157-5164.
21. Hodgson, D. A. & Chater, K. F. (1981). A chromosomal locus controlling extracellular agarase production by Streptomyces coelicolor A3(2) and its inactivation by chromosomal integration of plasmid SCP1. J Gen Microbiol 124, 339-348.
22. Hopwood, D. A., Bibb, M. J., Chater, K. F. & 7 other authors (1985). Genetic Manipulation of Streptomyces: a Laboratory Manual. Norwich: John Innes Foundation.
23. Ikeda, Y., Dabrowski, C. & Tanaka, K. (1983). Separation and properties of five distinct acyl-CoA dehydrogenases from rat liver mitochondria. J Biol Chem 258, 1066-1076.
24. Kadokami, Y. & Lewis, R. V. (1994). Repeated PCR of a gel band can be used to obtain a single PCR band. BioTechniques 17, 438.
25. Kelly, C. L., Hinsdale, M. E. & Wood, P. A. (1993). Cloning and characterization of the mouse short-chain acyl-CoA dehydrogenase cDNA. Genomics 18, 137-140.
26. Lebrihi, A., Lamsaif, D., Lefebvre, G. & Germain, P. (1992). Effect of ammonium ions on spiramycin biosynthesis in Streptomyces ambofaciens. Appl Microbiol Biotechnol 37, 382-387.
27. Massey, L. M., Sokatch, J. R. & Conrad, R. S. (1976). Branched-chain amino acid catabolism in bacteria. Bacteriol Rev 40, 42-54.
28. Matsubara, Y., Indo, Y., Naito, E., Ozasa, H., Glassberg, R., Vockley, J., Ikeda, Y., Kraus, J. & Tanaka, K. (1989). Molecular cloning and nucleotide sequence of cDNAs encoding the precursors of rat long chain acyl-coenzyme A, short chain acylcoenzyme A, and isovaleryl-coenzyme A dehydrogenases. Sequence homology of four enzymes of the acyl-CoA dehydrogenase family. J Biol Chem 264, 16321-16331.
29. Morelle, G. (1988). A plasmid extraction procedure on a miniprepscale. Focus 11, 7-8.
30. Naito, E., Ozasa, H., Ikeda, Y. & Tanaka, K. (1989). Molecular cloning and nucleotide sequence of complementary DNAs encoding human short chain acyl-coenzyme A dehydrogenase and the study of the molecular basis of human short chain acyl-coenzyme A dehydrogenase deficiency. J Clin Investig 83, 1605-1613.
31. Norman, E., De Smet, K. A., Stoker, N. G., Ratledge, C., Wheeler, P. R. & Dale, J. W. (1994). Lipid synthesis in mycobacteria : characterization of the biotin carboxyl carrier protein genes from Mycobacterium leprae and M. tuberculosis. J Bacteriol 176, 2525-2531.
32. Omura, S., Tsuzuki, K., Tanaka, Y., Sakakibara, H., Aizawa, M. & Lukacs, G. (1983). Valine as a precursor of the n-butyrate unit in the biosynthesis of macrolide aglycones. J Antibiot 36, 614-616.
33. Patel, S. S. & Walt, D. R. (1987). Substrate specificity of acetyl coenzyme A synthetase. J Biol Chem 262, 7132-7134.
34. Philipp, W. J., Poulet, S., Eiglmeier, K. & 7 other authors (1996). An integrated map of the genome of the tubercle bacillus, Mycobacterium tuberculosis H37Rv, and comparison with Mycobacterium leprae. Proc Natl Acad Sci USA 93, 3132-3137.
35. Reynolds, K. A., O'Hagen, D., Gani, D. & Robinson, J. A. (1988). Butyrate metabolism in streptomycetes. Characterization of an intramolecular vicinal interchange rearrangement linking isobutyrate and butyrate in Streptomyces cinnamonensis. J Chem Soc Perkin Trans I 1988, 3195-3208.
36. Reynolds, K. A., Wang, P., Fox, K. M., Lam, S., Speedie, M. K. & Floss, H. G. (1992). Purification and characterization of a novel enoyl coenzyme A reductase from Streptomyces collinus. J Bacteriol 174, 3850-3854.
37. Rozen, R., Vockley, J., Zhou, L. & 7 other authors (1994). Isolation and expression of a cDNA encoding the precursor for a novel member (ACADSB) of the acyl-CoA dehydrogenase gene family. Genomics 24, 280-287.
38. Sambrook, J., Fritsch, E. F. & Maniatis, T. (1989). Molecular Cloning: a Laboratory Manual, 2nd edn. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory.
39. Sherman, M. M., Yue, S. & Hutchinson, C. R. (1986). Biosynthesis of lasalocid A. Metabolic interrelationships of carboxylic acid precursors and polyether antibiotics. J Antibiot 39, 1135-1143.
40. Skinner, D. D. & Denoya, C. D. (1993). A simple DNA polymerase chain reaction method to locate and define orientation of specific sequences in cloned bacterial genomic fragments. Microbios 75, 125-129.
41. Skinner, D. D., Morgenstern, M. R., Fedechko, R. W. & Denoya, C. D. (1995). Cloning and sequencing of a cluster of genes encoding branched-chain α-keto acid dehydrogenase from Streptomyces avermitilis and the production of a functional E1[αβ] component in Escherichia coli. J Bacteriol 177, 183-190.
42. Sommer, R. & Tautz, D. (1989). Minimal homology requirements for PCR primers. Nucleic Acids Res 17, 6749.
43. Sood, G. R., Ashworth, D. M., Ajaz, A. A. & Robinson, J. A. (1988). Biosynthesis of the polyether antibiotic monensin A. Results from the incorporation of labeled acetate and propionate as a probe of the carbon chain assembly process. J Chem Soc Perkin Trans I 1988, 3183-3194.
44. Steele, M. I., Lorenz, D., Hatter, K., Park, A. & Sokatch, J. R. (1992). Characterization of the mmsAB operon of Pseudomonas aeruginosa PAO encoding methylmalonate semialdehyde dehydrogenase and 3-hydroxyisobutyrate dehydrogenase. J Biol Chem 267, 13585-13592.
45. Stutzman-Engwall, K. J., Otten, S. L. & Hutchinson, C. R. (1992). Regulation of secondary metabolism in Streptomyces spp. and the overproduction of daunorubicin in Streptomyces peucetius. J Bacteriol 174, 144-154.
46. Sykes, P. J., Burns, G., Menard, J., Hatter, K. & Sokatch, J. R. (1987). Molecular cloning of genes encoding branched-chain keto acid dehydrogenase of Pseudomonas putida. J Bacteriol 169, 1619-1625.
47. Tabor, S. (1990). Expression using the T7 RNA polymerase/promoter system. In Current Protocols in Molecular Biology, pp. 16.2.1-16.2.11. Edited by F. A. Ausubel, R. Brent, R. E. Kingston, D. D. Moore, J. G. Seidman, J. A. Smith & K. Struhl. New York: Greene Publishing and Wiley Interscience.
48. Tang, L. & Hutchinson, C. R. (1993). Sequence, transcriptional and functional analysis of the valine (branched-chain amino acid) dehydrogenase gene of Streptomyces coelicolor. J Bacteriol 175, 4176-4185.
49. Tang, L., Zhang, Y.-X. & Hutchinson, C. R. (1994). Amino acid catabolism and antibiotic synthesis: valine is a source of precursors for macrolide biosynthesis in Streptomyces ambofaciens and Streptomyces fradiae. J Bacteriol 176, 6107-6119.
50. Tosato, V., Albertini, A. M., Zotti, M., Sonda, S. & Bruschi, C. V. (1997). Sequence completion, identification and definition of the fengycin operon in Bacillus subtilis 168. Microbiology 143, 3443-3450.
51. Wexler, I. D., Hemalatha, S. G. & Patel, M. S. (1991). Sequence conservation in the α and β subunits of pyruvate dehydrogenase and its similarity to branched-chain α-keto acid dehydrogenase. FEBS Lett 282, 209-213.
52. Willard, J., Vicanek, C., Battaile, K., Van Veldhoven, P., Fauq, A., Rozen, R. & Vockley, J. (1996). Cloning of a cDNA for short/branched chain acyl-Coenzyme A dehydrogenase from rat and characterization of its tissue expression and substrate specificity. Arch Biochem Biophys 331, 127-133.
53. Wolf, D. A. & Akers, H. A. (1986). Uncertainties remain in the catabolism of valine. Trends Biochem Sci 11, 390-392.
54. Yanisch-Perron, C., Vieira, J. & Messing, J. (1985). Improved M13 phage cloning vectors and host strains: nucleotide sequences of the M13mp18 and pUC19 vectors. Gene 33, 103-119.
55. Zhang, Y.-X., Tang, L. & Hutchinson, C. R. (1996). Cloning and characterization of a homolog of the mmsA gene encoding methylmalonate-semialdehyde dehydrogenase from Streptomyces coelicolor. J Bacteriol 178, 490-495.