Metabolic Engineering of Pseudomonas putida for Methylmalonyl-CoA Biosynthesis to Enable Complex Heterologous Secondary Metabolite Formation

Chemistry & Biology - Tập 13 - Trang 1253-1264 - 2006
Frank Gross1,2,3, Michael W. Ring1, Olena Perlova1,2, Jun Fu4,3, Susan Schneider4, Klaus Gerth2, Silvia Kuhlmann1, A. Francis Stewart4, Youming Zhang3, Rolf Müller1
1Pharmaceutical Biotechnology, Saarland University, P.O. Box 151150, 66041 Saarbrücken, Germany
2German Research Centre for Biotechnology, Mascheroder Weg 1, 38124 Braunschweig, Germany
3Gene Bridges GmbH, Tatzberg 47-49, 01307 Dresden, Germany
4BioInnovationsZentrum, Department of Genomics, Technische Universität Dresden, Tatzberg 47-51, 01307 Dresden, Germany

Tài liệu tham khảo

Demain, 1999, Pharmaceutically active secondary metabolites of microorganisms, Appl. Microbiol. Biotechnol., 52, 455, 10.1007/s002530051546 Gräfe, 1999, Secondary metabolites: from past to present, 117 Mootz, 2002, Ways of assembling complex natural products on modular nonribosomal peptide synthetases, ChemBioChem, 3, 490, 10.1002/1439-7633(20020603)3:6<490::AID-CBIC490>3.0.CO;2-N Grabley, 1999, The impact of natural products on drug discovery, 3 Bode, 2005, The impact of bacterial genomics on natural product research, Angew. Chem. Int. Ed. Engl., 44, 6828, 10.1002/anie.200501080 Bentley, 2002, Complete genome sequence of the model actinomycete Streptomyces coelicolor A3(2), Nature, 417, 141, 10.1038/417141a Ikeda, 2003, Complete genome sequence and comparative analysis of the industrial microorganism Streptomyces avermitilis, Nat. Biotechnol., 21, 526, 10.1038/nbt820 Peláez, 2006, The historical delivery of antibiotics from microbial natural products: can history repeat?, Biochem Pharmacol, 71, 981, 10.1016/j.bcp.2005.10.010 Wenzel, 2005, Recent developments towards the heterologous expression of complex bacterial natural product biosynthetic pathways, Curr. Opin. Biotechnol., 16, 594, 10.1016/j.copbio.2005.10.001 Pfeifer, 2001, Biosynthesis of complex polyketides in a metabolically engineered strain of E. coli, Science, 291, 1790, 10.1126/science.1058092 Wenzel, 2005, Heterologous expression of a myxobacterial natural products assembly line in pseudomonads via red/ET recombineering, Chem. Biol., 12, 349, 10.1016/j.chembiol.2004.12.012 Gross, 2005, Posttranslational modification of myxobacterial carrier protein domains in Pseudomonas sp. by an intrinsic phosphopantetheinyl transferase, Appl. Microbiol. Biotechnol., 68, 66, 10.1007/s00253-004-1836-7 Nelson, 2001 Eggerer, 1960, On the mechanism of the cobamide coenzyme dependent isomerization of methylmalonyl-CoA to succinyl-CoA, J. Am. Chem. Soc., 82, 2643, 10.1021/ja01495a064 Bannerjee, 1970, Properties of purified methylmalonate semialdehyde dehydrogenase of Pseudomonas aeruginosa, J. Biol. Chem., 245, 1828, 10.1016/S0021-9258(19)77166-X Gerth, 2003, 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, 233, 10.1016/j.jbiotec.2003.07.015 Reichenbach, 1993, Biologically active secondary metabolites from myxobacteria, Biotechnol. Adv., 11, 219, 10.1016/0734-9750(93)90042-L Bode, 2006, Analysis of myxobacterial secondary metabolism goes molecular, J. Ind. Microbiol. Biotechnol., 33, 577, 10.1007/s10295-006-0082-7 Gerth, 2000, Studies on the biosynthesis of epothilones: the biosynthetic origin of the carbon skeleton, J. Antibiot. (Tokyo), 53, 1373, 10.7164/antibiotics.53.1373 Molnar, 2000, The biosynthetic gene cluster for the microtubule-stabilizing agents epothilones A and B from Sorangium cellulosum So ce90, Chem. Biol., 7, 97, 10.1016/S1074-5521(00)00075-2 Tang, 2000, Cloning and heterologous expression of the epothilone gene cluster, Science, 287, 640, 10.1126/science.287.5453.640 Ligon, 2002, Characterization of the biosynthetic gene cluster for the antifungal polyketide soraphen A from Sorangium cellulosum So ce26, Gene, 285, 257, 10.1016/S0378-1119(02)00396-7 Schupp, 1995, A Sorangium cellulosum (myxobacterium) gene cluster for the biosynthesis of the macrolide antibiotic soraphen A: cloning, characterization, and homology to polyketide synthase genes from actinomycetes, J. Bacteriol., 177, 3673, 10.1128/jb.177.13.3673-3679.1995 Silakowski, 1999, New lessons for combinatorial biosynthesis from myxobacteria: the myxothiazol biosynthetic gene cluster of Stigmatella aurantiaca DW4/3–1, J. Biol. Chem., 274, 37391, 10.1074/jbc.274.52.37391 Trowitzsch-Kienast, 1986, Antibiotika aus gleitenden Bakterien, XXVIII: Biosynthese des Myxothiazols in Myxococcus fulvus Mx f16, Liebigs Ann. Chem., 10, 93, 10.1002/jlac.198619860109 Altschul, 1990, Basic local alignment search tool, J. Mol. Biol., 215, 403, 10.1016/S0022-2836(05)80360-2 Bobik, 2001, Identification of the human methylmalonyl-CoA racemase gene based on the analysis of prokaryotic gene arrangements: implications for decoding the human genome, J. Biol. Chem., 276, 37194, 10.1074/jbc.M107232200 Marsh, 1989, Cloning and structural characterization of the genes coding for adenosylcobalamin-dependent methylmalonyl-CoA mutase from Propionibacterium shermanii, Biochem. J., 260, 345, 10.1042/bj2600345 Birch, 1993, Cloning, sequencing, and expression of the gene encoding methylmalonyl-coenzyme A mutase from Streptomyces cinnamonensis, J. Bacteriol., 175, 3511, 10.1128/jb.175.11.3511-3519.1993 Haller, 2000, Discovering new enzymes and metabolic pathways: conversion of succinate to propionate by Escherichia coli, Biochemistry, 39, 4622, 10.1021/bi992888d Jansen, 1989, Cloning of full-length methylmalonyl-CoA mutase from a cDNA library using the polymerase chain reaction, Genomics, 4, 198, 10.1016/0888-7543(89)90300-5 Wilkemeyer, 1990, Primary structure and activity of mouse methylmalonyl-CoA mutase, Biochem. J., 271, 449, 10.1042/bj2710449 Muyrers, 2000, ET-cloning: think recombination first, Genet. Eng. (N. Y.), 22, 77, 10.1007/978-1-4615-4199-8_6 Zhang, 2000, DNA cloning by homologous recombination in Escherichia coli, Nat. Biotechnol., 18, 1314, 10.1038/82449 Yuan, 2006, Chromosomal promoter replacement of the isoprenoid pathway for enhancing carotinoid production in E. coli, Metab. Eng., 8, 79, 10.1016/j.ymben.2005.08.005 Murli, 2003, Metabolic engineering of Escherichia coli for improved 6-deoxyerythronolide B production, J. Ind. Microbiol. Biotechnol., 30, 500, 10.1007/s10295-003-0073-x Salanitro, 1975, Quantitative method for the gas chromatographic analysis of short-chain monocarboxylic and dicarboxylic acids in fermentation media, Appl. Microbiol., 29, 374, 10.1128/AEM.29.3.374-381.1975 Perlova, 2006, Reconstitution of myxothiazol biosynthetic gene luster by Red/ET recombination and heterologous expression in Myxococcus xanthus, AEM, 10.1128/AEM.01503-06 Silakowski, 1999, New lessons for combinatorial biosynthesis from myxobacteria: the myxothiazol biosynthetic gene cluster of Stigmatella aurantiaca DW4/3–1, J. Biol. Chem., 274, 37391, 10.1074/jbc.274.52.37391 Daniel, 2004, The soil metagenome: a rich resource for the discovery of novel natural products, Curr. Opin. Biotechnol., 15, 199, 10.1016/j.copbio.2004.04.005 Martinez, 2004, Genetically modified bacterial strains and novel bacterial artificial chromosome shuttle vectors for constructing environmental libraries and detecting heterologous natural products in multiple expression hosts, Appl. Environ. Microbiol., 70, 2452, 10.1128/AEM.70.4.2452-2463.2004 Peric-Concha, 2003, Mining the microbial metabolome: a new frontier for natural product lead discovery, Drug Discov. Today, 8, 1078, 10.1016/S1359-6446(03)02901-5 Dayem, 2002, Metabolic engineering of a methylmalonyl-CoA mutase-epimerase pathway for complex polyketide biosynthesis in Escherichia coli, Biochemistry, 41, 5193, 10.1021/bi015593k Finking, 2002, Characterization of a new type of phosphopantetheinyl transferase for fatty acid and siderophore synthesis in Pseudomonas aeruginosa, J. Biol. Chem., 277, 50293, 10.1074/jbc.M205042200 Lambalot, 1996, A new enzyme superfamily: the phosphopantetheinyl transferases, Chem. Biol., 3, 923, 10.1016/S1074-5521(96)90181-7 Armstrong, 2000, Mechanistic diversity in a metalloenzyme superfamily, Biochemistry, 39, 13625, 10.1021/bi001814v Babbitt, 1997, Understanding enzyme superfamilies: chemistry as the fundamental determinant in the evolution of new catalytic activities, J. Biol. Chem., 272, 30591, 10.1074/jbc.272.49.30591 Korotkova, 2004, MeaB is a component of the methylmalonyl-CoA mutase complex required for protection of the enzyme from inactivation, J. Biol. Chem., 279, 13652, 10.1074/jbc.M312852200 Mori, 1997, Characterization, sequencing, and expression of the genes encoding a reactivating factor for glycerol-inactivated adenosylcobalamin-dependent diol dehydratase, J. Biol. Chem., 272, 32034, 10.1074/jbc.272.51.32034 Seifert, 2001, Identification and expression of the genes and purification and characterization of the gene products involved in reactivation of coenzyme B12-dependent glycerol dehydratase of Citrobacter freundii, Eur. J. Biochem., 268, 2369, 10.1046/j.1432-1327.2001.02123.x Marsh, 1989, Subunit interactions in Propionibacterium shermanii methylmalonyl-CoA mutase studied by analytical ultracentrifugation, Biochem. J., 260, 353, 10.1042/bj2600353 Staunton, 2001, Polyketide biosynthesis: a millennium review, Nat. Prod. Rep., 18, 380, 10.1039/a909079g Textor, 1997, Propionate oxidation in Escherichia coli: evidence for operation of a methylcitrate cycle in bacteria, Arch. Microbiol., 168, 428, 10.1007/s002030050518 Mutka, 2006, Heterologous production of epothilone C and D in Escherichia coli, Biochemistry, 45, 1321, 10.1021/bi052075r Aldor, 2002, Metabolic engineering of a novel propionate-independent pathway for the production of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) in recombinant Salmonella enterica serovar typhimurium, Appl. Environ. Microbiol., 68, 3848, 10.1128/AEM.68.8.3848-3854.2002 Sambrook, 2001 Bagdasarian, 1981, Specific-purpose plasmid cloning vectors: II. Broad host range, high copy number, RSF1010-derived vectors, and a host-vector system for gene cloning in Pseudomonas, Gene, 16, 237, 10.1016/0378-1119(81)90080-9 Miller, 1972 Pradella, 2002, Characterisation, genome size and genetic manipulation of the myxobacterium Sorangium cellulosum So ce56, Arch. Microbiol., 178, 484, 10.1007/s00203-002-0479-2 Meyer, 1978, The fluorescent pigment of Pseudomonas fluorescens: biosynthesis, purification and physiochemical properties, J. Gen. Microbiol., 107, 319, 10.1099/00221287-107-2-319 Zhang, 1998, A new logic for DNA engineering using recombination in Escherichia coli, Nat. Genet., 20, 123, 10.1038/2417 Chang, 1978, Construction and characterization of amplifiable multicopy DNA cloning vehicles derived from the P15A cryptic miniplasmid, J. Bacteriol., 134, 1141, 10.1128/JB.134.3.1141-1156.1978 Blomfield, 1991, Allelic exchange in Escherichia coli using the Bacillus subtilis sacB gene and a temperature-sensitive pSC101 replicon, Mol. Microbiol., 5, 1447, 10.1111/j.1365-2958.1991.tb00791.x Wang, 2006, An improved recombineering approach by adding RecA to lambda Red recombination, Mol. Biotechnol., 32, 43, 10.1385/MB:32:1:043 Hill, 1994, Cloning of genes involved in the synthesis of pyrrolnitrin from Pseudomonas fluorescens and role of pyrrolnitrin synthesis in biological control of plant disease, Appl. Environ. Microbiol., 60, 78, 10.1128/AEM.60.1.78-85.1994