The Insect Pathogen Serratia marcescens Db10 Uses a Hybrid Non-Ribosomal Peptide Synthetase-Polyketide Synthase to Produce the Antibiotic Althiomycin

PLoS ONE

Volumn 7, Issue 9, 2012, Pages

  Gerc, Amy J ^a   Song, Lijiang ^b   Challis, Gregory L ^b   Stanley Wall, Nicola R ^a   Coulthurst, Sarah J ^a  

^a UNIVERSITY OF DUNDEE   (United Kingdom)

^b UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALTHIOMYCIN; ANTIBIOTIC AGENT; DOLASTATIN 15; ENZYME; MALYNGAMIDE A; MIRABIMIDE E; NATURAL PRODUCT; NONRIBOSOMAL PEPTIDE SYNTHETASE; PHOSPHOPANTEITHEINYL TRANSFERASE; POLYKETIDE SYNTHASE; SINTOKAMIDE A; UNCLASSIFIED DRUG;

ANTIBIOTIC BIOSYNTHESIS; ARTICLE; BACILLUS SUBTILIS; BIOINFORMATICS; CHROMATOGRAPHY; CONTROLLED STUDY; GENE CLUSTER; GENE DELETION; GENE LOCUS; GENE MAPPING; MYXOCOCCALES; NONHUMAN; OPERON; PROTEIN ANALYSIS; PROTEIN EXPRESSION; SERRATIA MARCESCENS; SPECTROSCOPY; STAPHYLOCOCCUS AUREUS; STREPTOMYCES; WILD TYPE;

ANIMALS; BACTERIAL PROTEINS; COMPUTATIONAL BIOLOGY; INSECTS; PEPTIDE SYNTHASES; POLYKETIDE SYNTHASES; SERRATIA MARCESCENS; THIAZOLES;

HEXAPODA; MYXOCOCCALES; SERRATIA MARCESCENS; STREPTOMYCES;

EID: 84866503265     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0044673     Document Type: Article

References (44)

1. Spellberg B, Powers JH, Brass EP, Miller LG, Edwards JE Jr, (2004) Trends in antimicrobial drug development: implications for the future. Clin Infect Dis 38: 1279-1286.
2. Gwynn MN, Portnoy A, Rittenhouse SF, Payne DJ, (2010) Challenges of antibacterial discovery revisited. Ann N Y Acad Sci 1213: 5-19.
3. Challis GL, (2008) Genome mining for novel natural product discovery. Journal of medicinal chemistry 51: 2618-2628.
4. Zerikly M, Challis GL, (2009) Strategies for the Discovery of New Natural Products by Genome Mining. Chembiochem 10: 625-633.
5. Challis GL, (2008) Mining microbial genomes for new natural products and biosynthetic pathways. Microbiology 154: 1555-1569.
6. Kim J, Choi JN, Kim P, Sok DE, Nam SW, et al. (2009) LC-MS/MS profiling-based secondary metabolite screening of Myxococcus xanthus. Journal of microbiology and biotechnology 19: 51-54.
7. Keating TA, Walsh CT, (1999) Initiation, elongation, and termination strategies in polyketide and polypeptide antibiotic biosynthesis. Curr Opin Chem Biol 3: 598-606.
8. Finking R, Marahiel MA, (2004) Biosynthesis of nonribosomal peptides. Annu Rev Microbiol 58: 453-488.
9. Chan YA, Boyne MTII, Podevels AM, Klimowicz AK, Handelsman J, et al. (2006) Hydroxymalonyl-acyl carrier protein (ACP) and aminomalonyl-ACP are two additional type I polyketide synthase extender units. Proc Natl Acad Sci U S A 103: 14349-14354.
10. Chan YA, Podevels AM, Kevany BM, Thomas MG, (2009) Biosynthesis of polyketide synthase extender units. Natural Product Reports 26: 90-114.
11. Walsh CT, Gehring AM, Weinreb PH, Quadri LE, Flugel RS, (1997) Post-translational modification of polyketide and nonribosomal peptide synthases. Current opinion in chemical biology 1: 309-315.
12. Lambalot RH, Gehring AM, Flugel RS, Zuber P, LaCelle M, et al. (1996) A new enzyme superfamily- the phosphopantetheinyl transferases. Chem Biol 3: 923-936.
13. Fischbach MA, Walsh CT, (2006) Assembly-line enzymology for polyketide and nonribosomal Peptide antibiotics: logic, machinery, and mechanisms. Chem Rev 106: 3468-3496.
14. Yamaguchi H, Nakayama Y, Takeda K, Tawara K, Maeda K, et al. (1957) A new antibiotic, althiomycin. The Journal of antibiotics 10: 195-200.
15. Fujimoto H, Kinoshita T, Suzuki H, Umezawa H, (1970) Studies on the mode of action of althiomycin. J Antibiot (Tokyo) 23: 271-275.
16. Burns DJ, Cundliffe E, (1973) Bacterial-protein synthesis. A novel system for studying antibiotic action in vivo. Eur J Biochem 37: 570-574.
17. Sakakibara H, Naganawa H, Ono M, Maeda K, Umezawa H, (1974) The structure of althiomycin. The Journal of antibiotics 27: 897-899.
18. Inami K, Shiba T, (1985) Total Synthesis of Antibiotic Althiomycin. Bulletin of the Chemical Society of Japan 58: 352-360.
19. Zarantonello P, Leslie CP, Ferritto R, Kazmierski WM, (2002) Total synthesis and semi-synthetic approaches to analogues of antibacterial natural product althiomycin. Bioorganic & medicinal chemistry letters 12: 561-565.
20. Kunze B, Reichenbach H, Augustiniak H, Hofle G, (1982) Isolation and identification of althiomycin from Cystobacter fuscus (myxobacterales). The Journal of antibiotics 35: 635-636.
21. Cortina NS, Revermann O, Krug D, Muller R, (2011) Identification and characterization of the althiomycin biosynthetic gene cluster in Myxococcus xanthus DK897. Chembiochem 12: 1411-1416.
22. Harris AK, Williamson NR, Slater H, Cox A, Abbasi S, et al. (2004) The Serratia gene cluster encoding biosynthesis of the red antibiotic, prodigiosin, shows species- and strain-dependent genome context variation. Microbiology 150: 3547-3560.
23. Coulthurst SJ, Barnard AM, Salmond GP, (2005) Regulation and biosynthesis of carbapenem antibiotics in bacteria. Nat Rev Microbiol 3: 295-306.
24. Williamson NR, Fineran PC, Leeper FJ, Salmond GP, (2006) The biosynthesis and regulation of bacterial prodiginines. Nat Rev Microbiol 4: 887-899.
25. Flyg C, Kenne K, Boman HG, (1980) Insect pathogenic properties of Serratia marcescens: phage-resistant mutants with a decreased resistance to Cecropia immunity and a decreased virulence to Drosophila. J Gen Microbiol 120: 173-181.
26. Challis GL, Ravel J, Townsend CA, (2000) Predictive, structure-based model of amino acid recognition by nonribosomal peptide synthetase adenylation domains. Chemistry & biology 7: 211-224.
27. Stachelhaus T, Mootz HD, Marahiel MA, (1999) The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases. Chem Biol 6: 493-505.
28. Haydock SF, Aparicio JF, Molnar I, Schwecke T, Khaw LE, et al. (1995) Divergent sequence motifs correlated with the substrate specificity of (methyl)malonyl-CoA:acyl carrier protein transacylase domains in modular polyketide synthases. FEBS letters 374: 246-248.
29. Krebs C, Matthews ML, Jiang W, Bollinger JM Jr, (2007) AurF from Streptomyces thioluteus and a possible new family of manganese/iron oxygenases. Biochemistry 46: 10413-10418.
30. Pavlidou M, Pross EK, Musiol EM, Kulik A, Wohlleben W, et al. (2011) The phosphopantetheinyl transferase KirP activates the ACP and PCP domains of the kirromycin NRPS/PKS of Streptomyces collinus Tu 365. FEMS microbiology letters 319: 26-33.
31. Mootz HD, Finking R, Marahiel MA, (2001) 4′-phosphopantetheine transfer in primary and secondary metabolism of Bacillus subtilis. The Journal of biological chemistry 276: 37289-37298.
32. Quadri LE, Weinreb PH, Lei M, Nakano MM, Zuber P, et al. (1998) Characterization of Sfp, a Bacillus subtilis phosphopantetheinyl transferase for peptidyl carrier protein domains in peptide synthetases. Biochemistry 37: 1585-1595.
33. Fluman N, Bibi E, (2009) Bacterial multidrug transport through the lens of the major facilitator superfamily. Biochim Biophys Acta 1794: 738-747.
34. Hopwood DA, (2007) How do antibiotic-producing bacteria ensure their self-resistance before antibiotic biosynthesis incapacitates them? Mol Microbiol 63: 937-940.
35. Sadar MD, Williams DE, Mawji NR, Patrick BO, Wikanta T, et al. (2008) Sintokamides A to E, chlorinated peptides from the sponge Dysidea sp. that inhibit transactivation of the N-terminus of the androgen receptor in prostate cancer cells. Organic letters 10: 4947-4950.
36. Bai R, Friedman SJ, Pettit GR, Hamel E, (1992) Dolastatin 15, a potent antimitotic depsipeptide derived from Dolabella auricularia. Interaction with tubulin and effects of cellular microtubules. Biochemical pharmacology 43: 2637-2645.
37. Cardellina JH, Marner FJ, Moore RE, (1979) Malyngamide A, a Novel Chlorinated Metabolite of the Marine Cyanophyte Lyngbya-Majuscula. Journal of the American Chemical Society 101: 240-242.
38. Paik SG, Carmeli S, Cullingham J, Moore RE, Patterson GML, et al. (1994) Mirabimide-E, an Unusual N-Acylpyrrolinone from the Blue-Green-Alga Scytonema Mirabile- Structure Determination and Synthesis. Journal of the American Chemical Society 116: 8116-8125.
39. Coulthurst SJ, Williamson NR, Harris AK, Spring DR, Salmond GP, (2006) Metabolic and regulatory engineering of Serratia marcescens: mimicking phage-mediated horizontal acquisition of antibiotic biosynthesis and quorum-sensing capacities. Microbiology 152: 1899-1911.
40. Coulthurst SJ, Lilley KS, Salmond GP, (2006) Genetic and proteomic analysis of the role of luxS in the enteric phytopathogen, Erwinia carotovora. Molecular Plant Pathology 7: 31-45.
41. Altschul SF, Madden TL, Schaffer AA, Zhang J, Zhang Z, et al. (1997) Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Research 25: 3389-3402.
42. Petty NK, Foulds IJ, Pradel E, Ewbank JJ, Salmond GP, (2006) A generalized transducing phage (phiIF3) for the genomically sequenced Serratia marcescens strain Db11: a tool for functional genomics of an opportunistic human pathogen. Microbiology 152: 1701-1708.
43. Kiley TB, Stanley-Wall NR, (2010) Post-translational control of Bacillus subtilis biofilm formation mediated by tyrosine phosphorylation. Mol Microbiol 78: 947-963.
44. Jack RL, Buchanan G, Dubini A, Hatzixanthis K, Palmer T, et al. (2004) Coordinating assembly and export of complex bacterial proteins. The EMBO journal 23: 3962-3972.