Biosynthesis of taxadiene in saccharomyces cerevisiae: Selection of geranylgeranyl diphosphate synthase directed by a computer-aided docking strategy

PLoS ONE

Volumn 9, Issue 10, 2014, Pages

  Ding, Ming Zhu ^a,b   Yan, Hui Fang ^a,b   Li, Lin Feng ^b,c   Zhai, Fang ^a,b   Shang, Lu Qing ^b,c   Yin, Zheng ^b,c   Yuan, Ying Jin ^a,b  

^a TIANJIN UNIVERSITY   (China)

^b School of Science   (China)

^c NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CITRIC ACID; FARNESYL DIPHOSPHATE; FARNESYL TRANS TRANSFERASE; MEVALONIC ACID; TAXADIENE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG; ALKENE; DITERPENE; GERANYLGERANYL PYROPHOSPHATE; ISOPRENOID PHOSPHATE; SACCHAROMYCES CEREVISIAE PROTEIN; TAXA-4(5),11(12)DIENE;

AMINO ACID COMPOSITION; ARTICLE; BIOCATALYSIS; BIOENGINEERING; CARBON DYNAMICS; CITRIC ACID CYCLE; COMPUTER AIDED DESIGN; COMPUTER PROGRAM; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGAL METABOLISM; FUNGAL STRAIN; METABOLITE; METABOLOMICS; MOLECULAR DOCKING; NONHUMAN; PANTOEA AGGLOMERANS; PREDICTION; SACCHAROMYCES CEREVISIAE; SYNTHETIC BIOLOGY; TAXUS; TAXUS BACCATA; TAXUS CUSPIDATE; METABOLISM;

SACCHAROMYCES CEREVISIAE;

ALKENES; DITERPENES; POLYISOPRENYL PHOSPHATES; SACCHAROMYCES CEREVISIAE; SACCHAROMYCES CEREVISIAE PROTEINS;

EID: 84907822164     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0109348     Document Type: Article

References (36)

1. Bouvier F, Rahier A, Camara B (2005) Biogenesis, molecular regulation and function of plant isoprenoids. Prog Lipid Res 44:357-429.
2. Ajikumar PK, Tyo K, Carlsen S, Mucha O, Phon TH, et al. (2008) Terpenoids: Opportunities for biosynthesis of natural product drugs using engineered microorganisms. Mol Pharm 5:167-190.
3. Chang MCY, Keasling JD (2006) Production of isoprenoid pharmaceuticals by engineered microbes. Nat Chem Biol 2:674-681.
4. Conolly JD, Hill RA (1991) Dictionary of Terpenoids. Chapman & Hall London.
5. Ro DK, Ouellet M, Paradise EM, Burd H, Eng D, et al. (2008) Induction of multiple pleiotropic drug resistance genes in yeast engineered to produce an increased level of anti-malarial drug precursor, artemisinic acid. BMC Biotechnol 8:83.
6. Leonard E, Ajikumar PK, Thayer K, Xiao WH, Mo JD, et al. (2010) Combining metabolic and protein engineering of a terpenoid biosynthetic pathway for overproduction and selectivity control. PNAS 107:13654-13659.
7. Rico J, Pardo E, Orejas M (2010) Enhanced production of a plant monoterpene by overexpression of the 3-hydroxy-3-methylglutaryl coenzyme a reductase catalytic domain in Saccharomyces cerevisiae. Appl Environ Microb 76:6449-6454.
8. Carrau FM, Medina K, Boido E, Farina L, Gaggero C, et al. (2005) De novo synthesis of monoterpenes by Saccharomyces cerevisiae wine yeasts. FEMS Microbiol Lett 243:107-115.
9. DeJong JM, Liu YL, Bollon AP, Long RM, Jennewein S, et al. (2006) Genetic engineering of Taxol biosynthetic genes in Saccharomyces cerevisiae. Biotechnol Bioeng 93:212-224.
10. Martin VJJ, Pitera DJ, Withers ST, Newman JD, Keasling JD (2003) Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nature Biotech 21:796-802.
11. Ro DK, Paradise EM, Ouellet M, Fisher KJ, Newman KL, et al. (2006) Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature 440:940-943.
12. Zhou YJJ, Gao W, Rong QX, Jin GJ, Chu HY, et al. (2012) Modular pathway engineering of diterpenoid synthases and the mevalonic acid pathway for miltiradiene production. J Am Ceram Soc 134:3234-3241.
13. Engels B, Dahm P, Jennewein S (2008) Metabolic engineering of taxadiene biosynthesis in yeast as a first step towards Taxol (Paclitaxel) production. Metab Eng 10:201-206.
14. Dai Z, Liu Y, Huang L, Zhang X (2012) Production of miltiradiene by metabolically engineered Saccharomyces cerevisiae. Biotechnol Bioeng 109:2845-2853.
15. Farhi M, Marhevka E, Masci T, Marcos E, Eyal Y, et al. (2011) Harnessing yeast subcellular compartments for the production of plant terpenoids. Metab Eng 13:474-481.
16. Wang CW, Oh MK, Liao JC (1999) Engineered isoprenoid pathway enhances astaxanthin production in Escherichia coli. Biotechnol Bioeng 62:235-241.
17. Newman JD, Marshall J, Chang M, Nowroozi F, Paradise E, et al. (2006) Highlevel production of amorpha-4, 11-diene in a two-phase partitioning bioreactor of metabolically engineered Escherichia coli. Biotechnol Bioeng 95:684-691.
18. Ajikumar PK, Xiao WH, Tyo KEJ, Wang Y, Simeon F, et al. (2010) Isoprenoid pathway optimization for taxol precursor overproduction in Escherichia coli. Science 330:70-74.
19. Takahashi S, Yeo Y, Greenhagen BT, McMullin T, Song L, et al. (2007) Metabolic engineering of sesquiterpene metabolism in yeast. Biotechnol Bioeng 97:170-181.
20. Kirby J, Keasling JD (2009) Biosynthesis of plant isoprenoids: perspectives for microbial engineering. Annu Rev Plant Biol 60:335-355.
21. Kampranis SC and Makris AM (2012) Developing a yeast cell factory for the production of terpenoids. Comput Struct Biotechnol J. 3:e201210006.
22. Asadollahi MA, Maury J, Schalk M, Clark A, Nielsen J (2010) Enhancement of farnesyl diphosphate pool as direct precursor of sesquiterpenes through metabolic engineering of the mevalonate pathway in Saccharomyces cerevisiae. Biotechnol Bioeng 106:86-96.
23. Albertsen L, Chen Y, Bach LS, Rattleff S, Maury J, et al. (2011) Diversion of flux toward sesquiterpene production in Saccharomyces cerevisiae by fusion of host and heterologous enzymes. Appl Environ Microbiol 77:1033-1040.
24. Jiang Y, Proteau P, Poulter D and Ferro-Novick S (1995) BTS1 encodes a geranylgeranyl diphosphate synthase in Saccharomyces cerevisiae. J Biol Chem 270:21793-21799.
25. Chang TH, Guo RT, Ko TP, Wang AH, Liang PH (2006) Crystal structure of type-III geranylgeranyl pyrophosphate synthase from Saccharomyces cerevisiae and the mechanism of product chain length determination. J Biol Chem 281:14991-15000.
26. Boghigian BA, Armando J, Salas D, Pfeifer BA (2012) Computational identification of gene over-expression targets for metabolic engineering of taxadiene production. Appl Microbiol Biotechnol 93:2063-2073.
27. Kitchen DB, Decornez H, Furr JR, Bajorath J (2004) Docking and scoring in virtual screening for drug discovery: methods and applications. Nat Rev Drug Discov 3:935-949.
28. Cavasotto CN, Orry AJ (2007) Ligand docking and structure-based virtual screening in drug discovery. Curr Med Chem 7:1006-1014.
29. Urban A, Neukirchen S, Jaeger KE (1997) A rapid and efficient method for sitedirected mutagenesis using one-step overlap extension PCR. Nucleic Acids Res 25:2227-2228.
30. Ding MZ, Wang X, Yang Y, Yuan YJ (2012) Comparative metabolic profiling of parental and inhibitors-tolerant yeasts during lignocellulosic ethanol fermentation. Metabolomics 8:232-243.
31. Ding MZ, Zhou X, Yuan YJ (2010) Metabolome profiling reveals adaptive evolution of Saccharomyces cerevisiae during repeated vacuum fermentations. Metabolomics 6:42-55.
32. Molecular Operating Environment (MOE) (2013) Chemical Computing Group Inc., (http://www.chemcomp.com/). 1010 Sherbooke St West, Suite #910, Montreal, QC, Canada, H3A 2R7.
33. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, et al. (2009) AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem 30:2785-2791.
34. Shao ZY, Zhao H, Zhao HM (2009) DNA assembler, an in vivo genetic method for rapid construction of biochemical pathways. Nucleic Acids Res 37:e16.
35. Shalel-Levanon S, San KY, Bennett GN (2005) Effect of oxygen, and ArcA and FNR regulators on the expression of genes related to the electron transfer chain and the TCA cycle in Escherichia coli. Metab Eng 7:364-374.
36. Alexeeva S, Hellingwerf KJ, Teixeira de Mattos MJ (2002) Quantitative assessment of oxygen availability: perceived aerobiosis and its effect on flux distribution in the respiratory chain of Escherichia coli. J Bacteriol 184:1402-1406.