Combinatorial pathway engineering for optimized production of the anti-malarial FR900098

Biotechnology and Bioengineering

Volumn 113, Issue 2, 2016, Pages 384-392

  Freestone, Todd S ^a   Zhao, Huimin ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Anti malarial; FR900098; Metabolic engineering; Pathway engineering

Indexed keywords

ESCHERICHIA COLI; SCREENING; STRAIN;

ANTI-MALARIAL; COMBINATORIAL METHOD; ENRICHED LIBRARIES; FR900098; NATURALLY OCCURRING; OPTIMIZED PRODUCTION; PATHWAY ENGINEERINGS; SCREENING STRATEGY;

METABOLIC ENGINEERING;

ANTIMALARIAL AGENT; FR 900098; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GENE; BACTERIAL STRAIN; BACTERIUM CULTURE; BIOSYNTHESIS; COMBINATORIAL CHEMISTRY; DRUG DATABASE; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; ESCHERICHIA COLI; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLIC ENGINEERING; NONHUMAN; PLASMID; PROMOTER REGION; BIOTECHNOLOGY; GENETIC SCREENING; GENETICS; METABOLISM; MICROBIOLOGY; PHARMACEUTICS; PROCEDURES;

ANTIMALARIALS; BIOTECHNOLOGY; ESCHERICHIA COLI; GENETIC TESTING; INDUSTRIAL MICROBIOLOGY; METABOLIC ENGINEERING; METABOLIC NETWORKS AND PATHWAYS; ORGANOPHOSPHONATES; TECHNOLOGY, PHARMACEUTICAL;

EID: 84965008897     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.25719     Document Type: Article

References (35)

1. Ajikumar PK, Xiao WH, Tyo KEJ, Wang Y, Simeon F, Leonard E, Mucha O, Phon TH, Pfeifer B, Stephanopoulos G. 2010. Isoprenoid pathway optimization for taxol precursor overproduction in Escherichia coli. Science 330:70-74.
2. Bae B, Cobb RE, DeSieno MA, Zhao H, Nair SK. 2011. New N-acetyltransferase fold in the structure and mechanism of the phosphonate biosynthetic enzyme FrbF. J Biol Chem 286:36132-36141.
3. Bowman E, Mcqueney M, Barry RJ, Dunawaymariano D. 1988. Catalysis and thermodynamics of the phosphoenolpyruvate phosphonopyruvate rearrangement - Entry into the phosphonate class of naturally-occurring organo-phosphorus compounds. J Am Chem Soc 110:5575-5576.
4. Cobb RE, Bae B, Li Z, DeSieno MA, Nair SK, Zhao H. 2015. Structure-guided design and biosynthesis of a novel FR-900098 analogue as a potent Plasmodium falciparum 1-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr) inhibitor. Chem Commun 51:2526-2528.
5. Dondorp AM, Fairhurst RM, Slutsker L, MacArthur JR, Breman JG, Guerin PJ, Wellems TE, Ringwald P, Newman RD, Plowe CV. 2011. The threat of Artemisinin-resistant malaria. New Engl J Med 365:1073-1075.
6. Du J, Yuan YB, Si T, Lian JZ, Zhao HM. 2012. Customized optimization of metabolic pathways by combinatorial transcriptional engineering. Nucleic Acids Res 40.
7. Eisenreich W, Bacher A, Arigoni D, Rohdich F. 2004. Biosynthesis of isoprenoids via the non-mevalonate pathway. Cell Mol Life Sci 61:1401-1426.
8. Eliot AC, Griffin BM, Thomas PM, Johannes TW, Kelleher NL, Zhao HM, Metcalf WW. 2008. Cloning, expression, and biochemical characterization of streptomyces rubellomurinus genes required for biosynthesis of antimalarial compound FR900098. Chem Biol 15:765-770.
9. Engler C, Gruetzner R, Kandzia R, Marillonnet S. 2009. Golden Gate Shuffling: A One-Pot DNA Shuffling Method Based on Type IIs Restriction Enzymes. Plos One 4.
10. Farasat I, Kushwaha M, Collens J, Easterbrook M, Guido M, Salis HM. 2014. Efficient search, mapping, and optimization of multi-protein genetic systems in diverse bacteria. Mol Syst Biol 10.
11. Fokin AA, Yurchenko AG, Rodionov VN, Gunchenko PA, Yurchenko RI, Reichenberg A, Wiesner J, Hintz M, Jomaa H, Schreiner PR. 2007. Synthesis of the antimalarial drug FR900098 utilizing the nitroso-ene reaction. Organic Letters 9:4379-4382.
12. Gibson DG, Young L, Chuang RY, Venter JC, Hutchison CA, Smith HO. 2009. Enzymatic assembly of DNA molecules up to several hundred kilobases. Nat Methods 6:343-345.
13. Johannes TW. 2008. Directed evolution of phosphite dehydrogenase and engineered biosynthesis of FR-900098 [Dissertation]. Urbana, IL: University of Illinois at Urbana-Champaign.
14. Johannes TW, DeSieno MA, Griffin BM, Thomas PM, Kelleher NL, Metcalf WW, Zhao H. 2010. Deciphering the late biosynthetic steps of antimalarial compound FR-900098. Chem Biol 17:57-64.
15. Jomaa H, Wiesner J, Sanderbrand S, Altincicek B, Weidemeyer C, Hintz M, Turbachova I, Eberl M, Zeidler J, Lichtenthaler HK, Soldati D, Beck E. 1999. Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs. Science 285:1573-1576.
16. Kim B, Du J, Eriksen DT, Zhao HM. 2013. Combinatorial design of a highly efficient xylose-utilizing pathway in Saccharomyces cerevisiae for the production of cellulosic Biofuels. Appl Environ Microb 79:931-941.
17. Kuchner O, Arnold FH. 1997. Directed evolution of enzyme catalysts. Trends Biotechnol 15:523-530.
18. Latimer LN, Lee ME, Medina-Cleghorn D, Kohnz RA, Nomura DK, Dueber JE. 2014. Employing a combinatorial expression approach to characterize xylose utilization in Saccharomyces cerevisiae. Metab Eng 25:20-29.
19. Lee ME, Aswani A, Han AS, Tomlin CJ, Dueber JE. 2013. Expression-level optimization of a multi-enzyme pathway in the absence of a high-throughput assay. Nucleic Acids Res 41:10668-10678.
20. Metcalf WW, van der Donk WA. 2009. Biosynthesis of phosphonic and phosphinic acid natural products. Annu Rev Biochem 78:65-94.
21. Nowroozi FF, Baidoo EEK, Ermakov S, Redding-Johanson AM, Batth TS, Petzold CJ, Keasling JD. 2014. Metabolic pathway optimization using ribosome binding site variants and combinatorial gene assembly. Appl Microbiol Biot 98:1567-1581.
22. Okuhara M, Kuroda Y, Goto T, Okamoto M, Terano H, Kohsaka M, Aoki H, Imanaka H. 1980. Studies on new phosphonic acid antibiotics .1. Fr-900098, isolation and characterization. J Antibiot 33:13-17.
23. Perruchon J, Ortmann R, Schlitzer M. 2007. A novel short and efficient synthetic route to the antimalarial agent FR900098 and derivatives. Synthesis-Stuttgart 3553-3557.
24. Seidel HM, Freeman S, Seto H, Knowles JR. 1988. Phosphonate biosynthesis - isolation of the enzyme responsible for the formation of a carbon phosphorus bond. Nature 335:457-458.
25. Shao ZY, Zhao H, Zhao HM. 2009. DNA assembler, an in vivo genetic method for rapid construction of biochemical pathways. Nucleic Acids Res 37.
26. Smanski MJ, Bhatia S, Zhao DH, Park Y, Woodruff LBA, Giannoukos G, Ciulla D, Busby M, Calderon J, Nicol R, Gordon DB, Densmore D, Voigt CA. 2014. Functional optimization of gene clusters by combinatorial design and assembly. Nat Biotechnol 32:1241-U104.
27. Suresh S, Shyamraj D, Larhed M. 2013. Synthesis of antimalarial compounds fosmidomycin and FR900098 through N- or P-alkylation reactions. Tetrahedron 69:1183-1188.
28. Tahar R, Basco LK. 2007. Molecular epidemiology of malaria in Cameroon. XXV. In vitro activity of fosmidomycin and its derivatives against fresh clinical isolates of Plasmodium falciparum and sequence analysis of 1-Deoxy-D-Xylulose 5-phosphate reductoisomerase. Am J Trop Med Hyg 77:214-220.
29. Temme K, Hill R, Segall-Shapiro TH, Moser F, Voigt CA. 2012. Modular control of multiple pathways using engineered orthogonal T7 polymerases. Nucleic Acids Res 40:8773-8781.
30. Umeda T, Tanaka N, Kusakabe Y, Nakanishi M, Kitade Y, Nakamura KT. 2011. Molecular basis of fosmidomycin's action on the human malaria parasite Plasmodium falciparum. Sci Rep-Uk 1.
31. Wang M, Si T, Zhao HM. 2012. Biocatalyst development by directed evolution. Bioresource Technol 115:117-125.
32. Wanner BL, Metcalf WW. 1992. Molecular genetic-studies of a 10.9-Kb operon in Escherichia-Coli for Phosphonate Uptake and Biodegradation. Fems Microbiol Lett 100:133-139.
33. World Health Organization. 2013. World malaria report 2013. Geneva, Switzerland: World Health Organization.
34. Wu JJ, Du GC, Zhou JW, Chen J. 2013a. Metabolic engineering of Escherichia coli for (2S)-pinocembrin production from glucose by a modular metabolic strategy. Metab Eng 16:48-55.
35. Wu JJ, Liu PR, Fan YM, Bao H, Du GC, Zhou JW, Chen J. 2013b. Multivariate modular metabolic engineering of Escherichia coli to produce resveratrol from L-tyrosine. J Biotechnol 167:404-411.