Engineering of methionine chain elongation part of glucoraphanin pathway in E. coli

Metabolic Engineering

Volumn 35, Issue , 2016, Pages 31-37

  Mirza, Nadia ^a   Crocoll, Christoph ^a   Erik Olsen, Carl ^a   Ann Halkier, Barbara ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Aliphatic glucosinolates; Chain elongation pathway; Dihomo methionine; Glucoraphanin

Indexed keywords

CHAINS; DERIVATIVES; ELONGATION; ENZYMES; ESCHERICHIA COLI; GENE EXPRESSION; GENES;

CHAIN ELONGATION; DIHOMO-METHIONINE; EXPRESSION SYSTEM; GLUCORAPHANIN; GLUCOSINOLATES; METHIONINE PRODUCTION; MICROBIAL PRODUCTION; MICROBIAL SOURCES;

AMINO ACIDS;

AMINO ACID; GLUCORAPHANIN; GLUCOSINOLATE; LEUCINE; METHIONINE; UNCLASSIFIED DRUG; IMIDOESTER;

ARTICLE; CHLOROPLAST; CONTROLLED STUDY; CYTOSOL; ESCHERICHIA COLI; GENE EXPRESSION SYSTEM; METABOLIC ENGINEERING; NONHUMAN; PLANT GENE; PLASMID; PRIORITY JOURNAL; SYNTHESIS; TRANSCRIPTION ELONGATION; BIOSYNTHESIS; GENETICS; METABOLISM;

ESCHERICHIA COLI; GLUCOSINOLATES; IMIDOESTERS; METABOLIC ENGINEERING; METHIONINE;

EID: 84956858047     PISSN: 10967176     EISSN: 10967184     Source Type: Journal    
DOI: 10.1016/j.ymben.2015.09.012     Document Type: Article

References (50)

1. Armah C.N., Traka M.H., Dainty J.R., Defernez M., Janssens A., Leung W., Doleman J.F., Potter J.F., Mithen R.F. A diet rich in high-glucoraphanin broccoli interacts with genotype to reduce discordance in plasma metabolite profiles by modulating mitochondrial function. Am. J. Clin. Nutr. 2013, 98(3):712-722. 10.3945/ajcn.113.065235.
2. Atsumi S., Hanai T., Liao J.C. Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels. Nature 2008, 451(7174):86-89.
3. Benderoth M., Pfalz M., Kroymann J. Methylthioalkylmalate synthases: genetics, ecology and evolution. Phytochem. Rev. 2009, 8(1):255-268. 10.1007/s11101-008-9097-1.
4. Benderoth M., Textor S., Windsor A.J., Mitchell-Olds T., Gershenzon J., Kroymann J. Positive selection driving diversification in plant secondary metabolism. Proc. Natl. Acad. Sci. USA 2006, 103(24):9118-9123. 10.1073/pnas.0601738103.
5. Burow M., Losansky A., Muller R., Plock A., Kliebenstein D.J., Wittstock U. The genetic basis of constitutive and herbivore-induced ESP-independent nitrile formation in Arabidopsis. Plant Physiol. 2009, 149(1):561-574. 10.1104/pp.108.130732.
6. Chapple C.C.S., Decicco C., Ellis B.E. Biosynthesis of 2-(2'-methylthio)ethylmalate in Brassica carinata. Phytochemistry 1988, 27(11):3461-3463.
7. Chen S., Glawischnig E., Jorgensen K., Naur P., Jorgensen B., Olsen C.E., Hansen C.H., Rasmussen H., Pickett J.A., Halkier B.A. CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis. Plant J. 2003, 33(5):923-937.
8. Chisholm M.D., Wetter L.R. Biosynthesis of Mustard Oil Glucosides. IV. The administration of methionine-C14 and related compounds to horseradish. Can. J. Biochem. 1964, 42:1033-1040.
9. de Kraker J.W., Gershenzon J. From amino acid to glucosinolate biosynthesis: protein sequence changes in the evolution of methylthioalkylmalate synthase in Arabidopsis. Plant Cell 2011, 23(1):38-53. 10.1105/tpc.110.079269.
10. Docimo T., Reichelt M., Schneider B., Kai M., Kunert G., Gershenzon J., D'Auria J.C. The first step in the biosynthesis of cocaine in Erythroxylum coca: the characterization of arginine and ornithine decarboxylases. Plant Mol. Biol. 2012, 78(6):599-615. 10.1007/s11103-012-9886-1.
11. Docimo T., Reichelt M., Schneider B., Kai M., Kunert G., Gershenzon J., D'Auria J. The first step in the biosynthesis of cocaine in Erythroxylum coca: the characterization of arginine and ornithine decarboxylases. Plant Mol. Biol. 2012, 78(6):599-615. 10.1007/s11103-012-9886-1.
12. Engels B., Dahm P., Jennewein S. Metabolic engineering of taxadiene biosynthesis in yeast as a first step towards Taxol (Paclitaxel) production. Metab. Eng. 2008, 10(3-4):201-206. 10.1016/j.ymben.2008.03.001.
13. Farhi M., Marhevka E., Masci T., Marcos E., Eyal Y., Ovadis M., Abeliovich H., Vainstein A. Harnessing yeast subcellular compartments for the production of plant terpenoids. Metab. Eng. 2011, 13(5):474-481. 10.1016/j.ymben.2011.05.001.
14. Felnagle E.A., Chaubey A., Noey E.L., Houk K.N., Liao J.C. Engineering synthetic recursive pathways to generate non-natural small molecules. Nat. Chem. Biol. 2012, 8(6):518-526. 10.1038/nchembio.959.
15. Field B., Cardon G., Traka M., Botterman J., Vancanneyt G., Mithen R. Glucosinolate and amino acid biosynthesis in Arabidopsis. Plant Physiol. 2004, 135(2):828-839. 10.1104/pp.104.039347.
16. Fossati E., Ekins A., Narcross L., Zhu Y., Falgueyret J.P., Beaudoin G.A., Facchini P.J., Martin V.J. Reconstitution of a 10-gene pathway for synthesis of the plant alkaloid dihydrosanguinarine in Saccharomyces cerevisiae. Nat. Commun. 2014, 5:3283. 10.1038/ncomms4283.
17. Geu-Flores F., Nour-Eldin H.H., Nielsen M.T., Halkier B.A. USER fusion: a rapid and efficient method for simultaneous fusion and cloning of multiple PCR products. Nucleic Acids Res. 2007, 35(7):e55. 10.1093/nar/gkm106.
18. Geu-Flores F., Olsen C.E., Halkier B.A. Towards engineering glucosinolates into non-cruciferous plants. Planta 2009, 229(2):261-270. 10.1007/s00425-008-0825-y.
19. Graser G., Schneider B., Oldham N.J., Gershenzon J. The methionine chain elongation pathway in the biosynthesis of glucosinolates in Eruca sativa (Brassicaceae). Arch. Biochem. Biophys. 2000, 378(2):411-419. 10.1006/abbi.2000.1812.
20. Halkier B.A., Gershenzon J. Biology and biochemistry of glucosinolates. Annu. Rev. Plant Biol. 2006, 57:303-333. 10.1146/annurev.arplant.57.032905.105228.
21. Hansen C.H., Wittstock U., Olsen C.E., Hick A.J., Pickett J.A., Halkier B.A. Cytochrome p450 CYP79F1 from arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates. J. Biol. Chem. 2001, 276(14):11078-11085. 10.1074/jbc.M010123200.
22. He Y., Chen B., Pang Q., Strul J.M., Chen S. Functional specification of Arabidopsis isopropylmalate isomerases in glucosinolate and leucine biosynthesis. Plant Cell Physiol. 2010, 51(9):1480-1487. 10.1093/pcp/pcq113.
23. He Y., Mawhinney T.P., Preuss M.L., Schroeder A.C., Chen B., Abraham L., Jez J.M., Chen S. A redox-active isopropylmalate dehydrogenase functions in the biosynthesis of glucosinolates and leucine in Arabidopsis. Plant J. 2009, 60(4):679-690. 10.1111/j.1365-313X.2009.03990.x.
24. Jander G., Norris S.R., Joshi V., Fraga M., Rugg A., Yu S., Li L., Last R.L. Application of a high-throughput HPLC-MS/MS assay to Arabidopsis mutant screening; evidence that threonine aldolase plays a role in seed nutritional quality. Plant J. 2004, 39(3):465-475. 10.1111/j.1365-313X.2004.02140.x.
25. Kroymann J., Donnerhacke S., Schnabelrauch D., Mitchell-Olds T. Evolutionary dynamics of an Arabidopsis insect resistance quantitative trait locus. Proc. Natl. Acad. Sci. USA 2003, 100(Suppl. 2):S14587-S14592. 10.1073/pnas.1734046100.
26. Kroymann J., Textor S., Tokuhisa J.G., Falk K.L., Bartram S., Gershenzon J., Mitchell-Olds T. A gene controlling variation in Arabidopsis glucosinolate composition is part of the methionine chain elongation pathway. Plant Physiol. 2001, 127(3):1077-1088.
27. Leonard E., Yan Y., Koffas M.A.G. Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in Escherichia coli. Metab. Eng. 2006, 8(2):172-181. 10.1016/j.ymben.2005.11.001.
28. Lim H.N., Lee Y., Hussein R. Fundamental relationship between operon organization and gene expression. Proc. Natl. Acad. Sci. USA 2011, 108(26):10626-10631. 10.1073/pnas.1105692108.
29. Marcheschi R.J., Li H., Zhang K., Noey E.L., Kim S., Chaubey A., Houk K.N., Liao J.C. A synthetic recursive "+1" pathway for carbon chain elongation. ACS Chem. Biol. 2012, 7(4):689-697. 10.1021/cb200313e.
30. Martin V.J., Pitera D.J., Withers S.T., Newman J.D., Keasling J.D. Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nat. Biotechnol. 2003, 21(7):796-802. 10.1038/nbt833.
31. Mikkelsen M.D., Buron L.D., Salomonsen B., Olsen C.E., Hansen B.G., Mortensen U.H., Halkier B.A. Microbial production of indolylglucosinolate through engineering of a multi-gene pathway in a versatile yeast expression platform. Metab. Eng. 2012, 14(2):104-111. 10.1016/j.ymben.2012.01.006.
32. Mikkelsen M.D., Olsen C.E., Halkier B.A. Production of the cancer-preventive glucoraphanin in tobacco. Mol. Plant 2010, 3(4):751-759. 10.1093/mp/ssq020.
33. Minami H., Kim J.S., Ikezawa N., Takemura T., Katayama T., Kumagai H., Sato F. Microbial production of plant benzylisoquinoline alkaloids. Proc. Natl. Acad. Sci. USA 2008, 105(21):7393-7398. 10.1073/pnas.0802981105.
34. Mithen R. Glucosinolates - biochemistry, genetics and biological activity. Plant Growth Regul. 2001, 34(1):91-103. 10.1023/A:1013330819778.
35. Mora-Pale M., Sanchez-Rodriguez S.P., Linhardt R.J., Dordick J.S., Koffas M.A. Metabolic engineering and in vitro biosynthesis of phytochemicals and non-natural analogues. Plant Sci. 2013, 210:10-24. 10.1016/j.plantsci.2013.05.005.
36. Moreira D., Philippe H. Sure facts and open questions about the origin and evolution of photosynthetic plastids. Res. Microbiol. 2001, 152(9):771-780.
37. Nour-Eldin H.H., Geu-Flores F., Halkier B.A. USER cloning and USER fusion: the ideal cloning techniques for small and big laboratories. Methods Mol. Biol. 2010, 643:185-200. 10.1007/978-1-60761-723-5_13.
38. Pfalz M., Mikkelsen M.D., Bednarek P., Olsen C.E., Halkier B.A., Kroymann J. Metabolic engineering in Nicotiana benthamiana reveals key enzyme functions in Arabidopsis indole glucosinolate modification. Plant Cell 2011, 23(2):716-729. 10.1105/tpc.110.081711.
39. Romier C., Ben Jelloul M., Albeck S., Buchwald G., Busso D., Celie P.H., Christodoulou E., De Marco V., van Gerwen S., Knipscheer P., Lebbink J.H., Notenboom V., Poterszman A., Rochel N., Cohen S.X., Unger T., Sussman J.L., Moras D., Sixma T.K., Perrakis A. Co-expression of protein complexes in prokaryotic and eukaryotic hosts: experimental procedures, database tracking and case studies. Acta Crystallogr. D Biol. Crystallogr. 2006, 62(Pt. 10):1232-1242. 10.1107/S0907444906031003.
40. Rudman D., Meister A. Transamination in Escherichia coli. J. Biol. Chem. 1953, 200(2):591-604.
41. Schuster J., Knill T., Reichelt M., Gershenzon J., Binder S. Branched-chain aminotransferase4 is part of the chain elongation pathway in the biosynthesis of methionine-derived glucosinolates in Arabidopsis. Plant Cell 2006, 18(10):2664-2679. 10.1105/tpc.105.039339.
42. Shen C.R., Liao J.C. Metabolic engineering of Escherichia coli for 1-butanol and 1-propanol production via the keto-acid pathways. Metab. Eng. 2008, 10(6):312-320. 10.1016/j.ymben.2008.08.001.
43. Sonderby I.E., Geu-Flores F., Halkier B.A. Biosynthesis of glucosinolates - gene discovery and beyond. Trends Plant Sci. 2010, 15(5):283-290. 10.1016/j.tplants.2010.02.005.
44. Textor S., Bartram S., Kroymann J., Falk K.L., Hick A., Pickett J.A., Gershenzon J. Biosynthesis of methionine-derived glucosinolates in Arabidopsis thaliana: recombinant expression and characterization of methylthioalkylmalate synthase, the condensing enzyme of the chain-elongation cycle. Planta 2004, 218(6):1026-1035. 10.1007/s00425-003-1184-3.
45. Textor S., de Kraker J.W., Hause B., Gershenzon J., Tokuhisa J.G. MAM3 catalyzes the formation of all aliphatic glucosinolate chain lengths in Arabidopsis. Plant Physiol. 2007, 144(1):60-71. 10.1104/pp.106.091579.
46. Tolia N.H., Joshua-Tor L. Strategies for protein coexpression in Escherichia coli. Nat. Methods 2006, 3(1):55-64. 10.1038/nmeth0106-55.
47. Wang S., Zhang S., Xiao A., Rasmussen M., Skidmore C., Zhan J. Metabolic engineering of Escherichia coli for the biosynthesis of various phenylpropanoid derivatives. Metab. Eng. 2015, 29:153-159. 10.1016/j.ymben.2015.03.011.
48. Weng J.K., Philippe R.N., Noel J.P. The rise of chemodiversity in plants. Science 2012, 336(6089):1667-1670. 10.1126/science.1217411.
49. Zhang K., Sawaya M.R., Eisenberg D.S., Liao J.C. Expanding metabolism for biosynthesis of nonnatural alcohols. Proc. Natl. Acad. Sci. USA 2008, 105(52):20653-20658. 10.1073/pnas.0807157106.
50. Zhang X., Li M., Agrawal A., San K.-Y. Efficient free fatty acid production in Escherichia coli using plant acyl-ACP thioesterases. Metab. Eng. 2011, 13(6):713-722. 10.1016/j.ymben.2011.09.007.