Non-modular polyketide synthases in myxobacteria

Phytochemistry

Volumn 70, Issue 15-16, 2009, Pages 1850-1857

  Li, Yanyan ^a   Müller, Rolf ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Aurachin; Genome mining; Myxobacteria; Type III polyketide synthase

Indexed keywords

AURACHIN A; POLYKETIDE SYNTHASE; QUINOLINE DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; ENZYMOLOGY; METABOLISM; MYXOCOCCALES; REVIEW;

MOLECULAR STRUCTURE; MYXOCOCCALES; POLYKETIDE SYNTHASES; QUINOLINES;

BACTERIA (MICROORGANISMS); MYXOCOCCALES; STIGMATELLA AURANTIACA;

EID: 70350742041     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2009.05.003     Document Type: Review

References (53)

1. Abe I. Engineering of plant polyketide biosynthesis. Chem. Pharm. Bull. 56 (2008) 1505-1514
2. Achkar J., Xian M., Zhao H., and Frost J.W. Biosynthesis of phloroglucinol. J. Am. Chem. Soc. 127 (2005) 5332-5333
3. Austin M.B., and Noel J.P. The chalcone synthase superfamily of type III polyketide synthases. Nat. Prod. Rep. 20 (2003) 79-110
4. Austin M.B., Izumikawa M., Bowman M.E., Udwary D.W., Ferrer J.L., Moore B.S., and Noel J.P. Crystal structure of a bacterial type III polyketide synthase and enzymatic control of reactive polyketide intermediates. J. Biol. Chem. 279 (2004) 45162-45174
5. Bentley S.D., Chater K.F., Cerdeno-Tarraga A.M., Challis G.L., Thomson N.R., James K.D., Harris D.E., Quail M.A., Kieser H., Harper D., Bateman A., Brown S., Chandra G., Chen C.W., Collins M., Cronin A., Fraser A., Goble A., Hidalgo J., Hornsby T., Howarth S., Huang C.H., Kieser T., Larke L., Murphy L., Oliver K., O'Neil S., Rabbinowitsch E., Rajandream M.A., Rutherford K., Rutter S., Seeger K., Saunders D., Sharp S., Squares R., Squares S., Taylor K., Warren T., Wietzorrek A., Woodward J., Barrell B.G., Parkhill J., and Hopwood D.A. Complete genome sequence of the model actinomycete Streptomyces coelicolor A3(2). Nature 417 (2002) 141-147
6. Berner M., Krug D., Bihlmaier C., Vente A., Müller R., and Bechthold A. Genes and enzymes involved in caffeic acid biosynthesis in the actinomycete Saccharothrix espanaensis. J. Bacteriol. 188 (2006) 2666-2673
7. Brachmann A.O., Joyce S.A., Jenke-Kodama H., Schwär G., Clarke D.J., and Bode H.B. A type II polyketide synthase is responsible for anthraquinone biosynthesis in Photorhabdus luminescens. ChemBioChem 8 (2007) 1721-1728
8. Funa N., Ohnishi Y., Fujii I., Shibuya M., Ebizuka Y., and Horinouchi S. A new pathway for polyketide synthesis in microorganisms. Nature 400 (1999) 897-899
9. Funa N., Ozawa H., Hirata A., and Horinouchi S. Phenolic lipid synthesis by type III polyketide synthases is essential for cyst formation in Azotobacter vinelandii. Proc. Natl. Acad. Sci. USA 103 (2006) 6356-6361
10. Funabashi M., Funa N., and Horinouchi S. Phenolic lipids synthesized by type III polyketide synthase confer penicillin resistance on Streptomyces griseus. J. Biol. Chem. 283 (2008) 13983-13991
11. Funayama S., Ishibashi M., Komiyama K., and Omura S. Biosynthesis of furaquinocins A and B. J. Org. Chem. 55 (1990) 1132-1133
12. Gerth K., Jansen R., Reifenstahl G., Höfle G., Irschik H., Kunze B., Reichenbach H., and Thierbach G. The myxalamids, new antibiotics from Myxococcus xanthus (Myxobacterales). I. Production, physico-chemical and biological properties, and mechanism of action. J. Antibiot. 36 (1983) 1150-1156
13. Gerth K., Pradella S., Perlova O., Beyer S., and Müller R. Myxobacteria: proficient producers of novel natural products with various biological activities - past and future biotechnological aspects with the focus on the genus Sorangium. J. Biotechnol. 106 (2003) 233-253
14. Goldman B.S., Nierman W.C., Kaiser D., Slater S.C., Durkin A.S., Eisen J., Ronning C.M., Barbazuk W.B., Blanchard M., Field C., Halling C., Hinkle G., Iartchuk O., Kim H.S., Mackenzie C., Madupu R., Miller N., Shvartsbeyn A., Sullivan S.A., Vaudin M., Wiegand R., and Kaplan H.B. Evolution of sensory complexity recorded in a myxobacterial genome. Proc. Natl. Acad. Sci. USA 103 (2006) 15200-15205
15. Gross F., Luniak N., Perlova O., Gaitatzis N., Jenke-Kodama H., Gerth K., Gottschalk D., Dittmann E., and Müller R. Bacterial type III polyketide synthases: phylogenetic analysis and potential for the production of novel secondary metabolites by heterologous expression in pseudomonads. Arch. Microbiol. 185 (2006) 28-38
16. Grüschow S., Buchholz T.J., Seufert W., Dordick J.S., and Sherman D.H. Substrate profile analysis and ACP-mediated acyl transfer in Streptomyces coelicolor type III polyketide synthases. ChemBioChem 8 (2007) 863-868
17. Hertweck C., Luzhetskyy A., Rebets Y., and Bechthold A. Type II polyketide synthases: gaining a deeper insight into enzymatic teamwork. Nat. Prod. Rep. 24 (2007) 162-190
18. Höfle G., and Kunze B. Biosynthesis of aurachins A-L in Stigmatella aurantiaca: a feeding study. J. Nat. Prod. 71 (2008) 1843-1849
19. Izumikawa M., Shipley P.R., Hopke J.N., O'Hare T., Xiang L., Noel J.P., and Moore B.S. Expression and characterization of the type III polyketide synthase 1,3,6,8-tetrahydroxynaphthalene synthase from Streptomyces coelicolor A3(2). J. Ind. Microbiol. Biotechnol. 30 (2003) 510-515
20. Izumikawa M., Cheng Q., and Moore B.S. Priming type II polyketide synthases via a type II nonribosomal peptide synthetase mechanism. J. Am. Chem. Soc. 128 (2006) 1428-1429
21. Jenke-Kodama H., Sandmann A., Müller R., and Dittmann E. Evolutionary implications of bacterial polyketide synthases. Mol. Biol. Evol. 22 (2005) 2027-2039
22. Jenke-Kodama H., Müller R., and Dittmann E. Evolutionary mechanisms underlying secondary metabolite diversity. In: Petersen F., and Amstutz R. (Eds). Natural Compounds as Drugs (2008), Birkhäuser, Basel 120-140
23. Jiang Z., Swem L.R., Rushing B.G., Devanathan S., Tollin G., and Bauer C.E. Bacterial photoreceptor with similarity to photoactive yellow protein and plant phytochromes. Science 285 (1999) 406-409
24. Jiang C.G., Kim S.Y., and Suh D.Y. Divergent evolution of the thiolase superfamily and chalcone synthase family. Mol. Phylogenet. Evol. 49 (2008) 691-701
25. Kawasaki T., Hayashi Y., Kuzuyama T., Furihata K., Itoh N., Seto H., and Dairi T. Biosynthesis of a natural polyketide-isoprenoid hybrid compound, furaquinocin A: identification and heterologous expression of the gene cluster. J. Bacteriol. 188 (2006) 1236-1244
26. Kazuo S.Y., Furihata K., Hayakawa Y., and Seto H. Biosynthetic studies of naphterpin, a terpenoid metabolite of Streptomyces. Tetrahedron Lett. 31 (1990) 6025-6026
27. Kroken S., Glass N.L., Taylor J.W., Yoder O.C., and Turgeon B.G. Phylogenomic analysis of type I polyketide synthase genes in pathogenic and saprobic ascomycetes. Proc. Natl. Acad. Sci. USA 100 (2003) 15670-15675
28. Krug D., and Müller R. Discovery of additional members of the tyrosine aminomutase enzyme family and the mutational analysis of CmdF. ChemBioChem 10 (2009) 741-750
29. Kunze B., Kemmer T., Höfle G., and Reichenbach H. Stigmatellin, a new antibiotic from Stigmatella aurantiaca (Myxobacterales). I. Production, physico-chemical and biological properties. J. Antibiot. 37 (1984) 454-461
30. Kunze B., Höfle G., and Reichenbach H. The aurachins, new quinoline antibiotics from myxobacteria: production, physico-chemical and biological properties. J. Antibiot. 40 (1987) 258-265
31. Kuzuyama T., Noel J.P., and Richard S.B. Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products. Nature 435 (2005) 983-987
32. Kyndt J.A., Meyer T.E., Cusanovich M.A., and Van Beeumen J.J. Characterization of a bacterial tyrosine ammonia lyase, a biosynthetic enzyme for the photoactive yellow protein. FEBS Lett. 512 (2002) 240-244
33. Lepine F., Milot S., Deziel E., He J.X., and Rahme L.G. Electrospray/mass spectrometric identification and analysis of 4-hydroxy-2-alkylquinolines (HAQs) produced by Pseudomonas aeruginosa. J. Am. Soc. Mass Spectrom. 15 (2004) 862-869
34. Li T.L., Choroba O.W., Hong H., Williams D.H., and Spencer J.B. Biosynthesis of the vancomycin group of antibiotics: characterisation of a type III polyketide synthase in the pathway to (S)-3, 5-dihydroxyphenylglycine. Chem. Commun. 20 (2001) 2156-2157
35. Miyanaga A., Funa N., Awakawa T., and Horinouchi S. Direct transfer of starter substrates from type I fatty acid synthase to type III polyketide synthases in phenolic lipid synthesis. Proc. Natl. Acad. Sci. USA 105 (2008) 871-876
36. Mizuuchi Y., Shimokawa Y., Wanibuchi K., Noguchi H., and Abe I. Structure function analysis of novel type III polyketide synthases from Arabidopsis thaliana. Biol. Pharm. Bull. 31 (2008) 2205-2210
37. Moffitt M.C., Louie G.V., Bowman M.E., Pence J., Noel J.P., and Moore B.S. Discovery of two cyanobacterial phenylalanine ammonia lyases: kinetic and structural characterization. Biochemistry 46 (2007) 1004-1012
38. Moore B.S., and Höpke J.N. Discovery of a new bacterial polyketide biosynthetic pathway. ChemBioChem 2 (2001) 35-38
39. Oja T., Palmu K., Lehmussola H., Lepparanta O., Hannikainen K., Niemi J., Mantsala P., and Metsa-Ketela M. Characterization of the alnumycin gene cluster reveals unusual gene products for pyran ring formation and dioxan biosynthesis. Chem. Biol. 15 (2008) 1046-1057
40. Omura S., Ikeda H., Ishikawa J., Hanamoto A., Takahashi C., Shinose M., Takahashi Y., Horikawa H., Nakazawa H., Osonoe T., Kikuchi H., Shiba T., Sakaki Y., and Hattori M. Genome sequence of an industrial microorganism Streptomyces avermitilis: deducing the ability of producing secondary metabolites. Proc. Natl. Acad. Sci. USA 98 (2001) 12215-12220
41. Ronning C.M., and Nierman W.C. The genomes of Myxococcus xanthus and Stigmatella aurantiaca. In: Whitworth D. (Ed). Myxobacteria: Multicellularity and Differentiation (2007), ASM Press, Chicago 285-298
42. Sandmann A., Dickschat J., Jenke-Kodama H., Kunze B., Dittmann E., and Müller R. A type II polyketide synthase from the gram-negative bacterium Stigmatella aurantiaca is involved in aurachin alkaloid biosynthesis. Angew. Chem. Int. Ed. 46 (2007) 2712-2716
43. Saxena P., Yadav G., Mohanty D., and Gokhale R.S. A new family of type III polyketide synthases in Mycobacterium tuberculosis. J. Biol. Chem. 278 (2003) 44780-44790
44. Schneiker S., Perlova O., Kaiser O., Gerth K., Alici A., Altmeyer M.O., Bartels D., Bekel T., Beyer S., Bode E., Bode H.B., Bolten C.J., Choudhuri J.V., Doss S., Elnakady Y.A., Frank B., Gaigalat L., Goesmann A., Groeger C., Gross F., Jelsbak L., Jelsbak L., Kalinowski J., Kegler C., Knauber T., Konietzny S., Kopp M., Krause L., Krug D., Linke B., Mahmud T., Martinez-Arias R., McHardy A.C., Merai M., Meyer F., Mormann S., Munoz-Dorado J., Perez J., Pradella S., Rachid S., Raddatz G., Rosenau F., Ruckert C., Sasse F., Scharfe M., Schuster S.C., Suen G., Treuner-Lange A., Velicer G.J., Vorholter F.J., Weissman K.J., Welch R.D., Wenzel S.C., Whitworth D.E., Wilhelm S., Wittmann C., Blöcker H., Pühler A., and Müller R. Complete genome sequence of the myxobacterium Sorangium cellulosum. Nat. Biotechnol. 25 (2007) 1281-1289
45. Silakowski B., Kunze B., and Müller R. Stigmatella aurantiaca Sg a15 carries genes encoding type I and type II 3-deoxy-d-arabino-heptulosonate-7-phosphate synthases: involvement of a type II synthase in aurachin biosynthesis. Arch. Microbiol. 173 (2000) 403-411
46. Smith S., and Tsai S.C. The type I fatty acid and polyketide synthases: a tale of two megasynthases. Nat. Prod. Rep. 24 (2007) 1041-1072
47. Song L., Barona-Gomez F., Corre C., Xiang L., Udwary D.W., Austin M.B., Noel J.P., Moore B.S., and Challis G.L. Type III polyketide synthase beta-ketoacyl-ACP starter unit and ethylmalonyl-CoA extender unit selectivity discovered by Streptomyces coelicolor genome mining. J. Am. Chem. Soc. 128 (2006) 14754-14755
48. Thierbach G., and Reichenbach H. Myxothiazol, a new inhibitor of the cytochrome b-c1 segment of the respiratory chain. Biochim. Biophys. Acta 638 (1981) 282-289
49. Weissman K.J., and Müller R. A brief tour of myxobacterial secondary metabolism. Bioorg. Med. Chem. 17 (2009) 2121-2136
50. Wenzel S.C., and Müller R. Recent developments towards the heterologous expression of complex bacterial natural product biosynthetic pathways. Curr. Opin. Biotechnol. 16 (2005) 594-606
51. Williams J.S., Thomas M., and Clarke D.J. The gene stlA encodes a phenylalanine ammonia-lyase that is involved in the production of a stilbene antibiotic in Photorhabdus luminescens TT01. Microbiology 151 (2005) 2543-2550
52. Winter J.M., Moffitt M.C., Zazopoulos E., McAlpine J.B., Dorrestein P.C., and Moore B.S. Molecular basis for chloronium-mediated meroterpene cyclization: cloning, sequencing, and heterologous expression of the napyradiomycin biosynthetic gene cluster. J. Biol. Chem. 282 (2007) 16362-16368
53. Xiang L., and Moore B.S. Biochemical characterization of a prokaryotic phenylalanine ammonia lyase. J. Bacteriol. 187 (2005) 4286-4289