Production of mesaconate in Escherichia coli by engineered glutamate mutase pathway

Metabolic Engineering

Volumn 30, Issue , 2015, Pages 190-196

  Wang, Jingyu ^a   Zhang, Kechun ^a  

^a University of Minnesota   (United States)

Author keywords

3 Methylaspartate ammonia lyase; Adenosylcobalamin; Escherichia coli; Glutamate mutase; Mesaconate

Indexed keywords

AMMONIA; BIOCHEMISTRY; BIODEGRADATION; BIOSYNTHESIS; ESCHERICHIA COLI;

ADENOSYLCOBALAMIN; AMMONIA LYASE; BIOSYNTHETIC PATHWAY; DEGRADATION PATHWAYS; E. COLI; GLUTAMATE MUTASE; MESACONATE; SHAKE FLASKS;

METABOLIC ENGINEERING;

3 METHYLASPARTATE AMMONIA LYASE; AMMONIA LYASE; BACTERIAL ENZYME; COBAMAMIDE; DICARBOXYLIC ACID; GLUCOSE; GLUTAMATE MUTASE; GLUTAMIC ACID; MESACONIC ACID; MUTASE; UNCLASSIFIED DRUG; BACTERIAL PROTEIN; CITRACONIC ACID; FUMARIC ACID DERIVATIVE; MALEIC ACID DERIVATIVE; METHYLASPARTATE MUTASE;

ARTICLE; BIOSYNTHESIS; BIOTECHNOLOGICAL PRODUCTION; CLOSTRIDIUM TETANOMORPHUM; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME ENGINEERING; ESCHERICHIA COLI; FERMENTATION; IN VIVO STUDY; NONHUMAN; PRIORITY JOURNAL; SIGNAL TRANSDUCTION; ENZYMOLOGY; GENETICS; METABOLISM;

CLOSTRIDIUM TETANOMORPHUM; ESCHERICHIA COLI;

BACTERIAL PROTEINS; CLOSTRIDIUM TETANOMORPHUM; ESCHERICHIA COLI; FUMARATES; INTRAMOLECULAR TRANSFERASES; MALEATES;

EID: 84937028256     PISSN: 10967176     EISSN: 10967184     Source Type: Journal    
DOI: 10.1016/j.ymben.2015.06.001     Document Type: Article

References (45)

1. Apelblat A. Citric Acid 2014, Springer International Publishing, Switzerland.
2. Barker H.A., Rooze V., Suzuki F., Iodice A.A. The glutamate mutase system. assays and properties. J. Biol. Chem. 1964, 239:3260-3266.
3. Barker H.A., Smyth R.D., Wilson R.M., Weissbach H. The purification and properties of beta-methylaspartase. J. Biol. Chem. 1959, 234:320-328.
4. Bennett B.D., Kimball E.H., Gao M., Osterhout R., Van Dien S.J., Rabinowitz J.D. Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli. Nat. Chem. Biol. 2009, 5:593-599.
5. Biebl H., Menzel K., Zeng A.P., Deckwer W.D. Microbial production of 1,3-propanediol. Appl. Microbiol. Biotechnol. 1999, 52:289-297.
6. Bobik T.A., Havemann G.D., Busch R.J., Williams D.S., Aldrich H.C. The propanediol utilization (pdu) operon of Salmonella enterica serovar Typhimurium LT2 includes genes necessary for formation of polyhedral organelles involved in coenzyme B(12)-dependent 1, 2-propanediol degradation. J. Bacteriol. 1999, 181:5967-5975.
7. Bradbeer C., Kenley J.S., Di Masi D.R., Leighton M. Transport of vitamin B12 in Escherichia coli. Corrinoid specificities of the periplasmic B12-binding protein and of energy-dependent B12 transport. J. Biol. Chem. 1978, 253:1347-1352.
8. Buckel W., Barker H.A. Two pathways of glutamate fermentation by anaerobic bacteria. J. Bacteriol. 1974, 117:1248-1260.
9. Chen H.P., Marsh E.N. Adenosylcobalamin-dependent glutamate mutase: examination of substrate and coenzyme binding in an engineered fusion protein possessing simplified subunit structure and kinetic properties. Biochemistry 1997, 36:14939-14945.
10. Currier, G.H., Gerald, K.H., Ellis, S.A., 1972. Flame-Retardant Agents for Thermoplastic Products. U.S. Patent 3654342A.
11. de Villiers M., Puthan Veetil V., Raj H., de Villiers J., Poelarends G.J. Catalytic mechanisms and biocatalytic applications of aspartate and methylaspartate ammonia lyases. ACS Chem. Biol. 2012, 7:1618-1628.
12. Dunn-Coleman, N.S., Gatenby, A.A., Valle, F., 2006. Method for the Production of 1,3-propanediol by Recombinant Organisms Comprising genes for Coenzyme B12 Synthesis. U.S. Patent 7074608 B1.
13. Fonseca M.V., Escalante-Semerena J.C. An in vitro reducing system for the enzymic conversion of cobalamin to adenosylcobalamin. J. Biol. Chem. 2001, 276:32101-32108.
14. Goda S.K., Minton N.P., Botting N.P., Gani D. Cloning, sequencing, and expression in Escherichia coli of the Clostridium tetanomorphum gene encoding beta-methylaspartase and characterization of the recombinant protein. Biochemistry 1992, 31:10747-10756.
15. Halpern J. Mechanisms of coenzyme B12-dependent rearrangements. Science 1985, 227:869-875.
16. Heberling M.M., Wu B., Bartsch S., Janssen D.B. Priming ammonia lyases and aminomutases for industrial and therapeutic applications. Curr. Opin. Chem. Biol. 2013, 17:250-260.
17. Holloway D.E., Harding S.E., Marsh E.N. Adenosylcobalamin-dependent glutamate mutase: properties of a fusion protein in which the cobalamin-binding subunit is linked to the catalytic subunit. Biochem. J. 1996, 320(Pt 3):825-830.
18. Holloway D.E., Marsh E.N. Adenosylcobalamin-dependent glutamate mutase from Clostridium tetanomorphum. Overexpression in Escherichia coli, purification, and characterization of the recombinant enzyme. J. Biol. Chem. 1994, 269:20425-20430.
19. Holloway D.E., Marsh E.N.G. Cloning and sequencing of glutamate mutase component E from Clostridium tetanomorphum: organization of the mut genes. FEBS Lett. 1993, 317:44-48.
20. Huhta M.S., Ciceri D., Golding B.T., Marsh E.N.G. A Novel reaction between adenosylcobalamin and 2-methyleneglutarate catalyzed by glutamate mutase. Biochemistry 2002, 41:3200-3206.
21. Imaizumi A., Kojima H., Matsui K. The effect of intracellular ppGpp levels on glutamate and lysine overproduction in Escherichia coli. J. Biotechnol. 2006, 125:328-337.
22. Johnson, D.W., Eastham, G.R., Poliakoff, M., Huddle, T.A., 2013. Process for the Production of Methacrylic Acid and its Derivatives and Polymers Produced Therefrom. U.S. Patent 20130303713 A1.
23. Kropa, E.L., 1950. Polymers and copolymers of unsaturated triazines. U.S. Patent 2510503A.
24. Lawrence J.G., Roth J.R. Evolution of coenzyme B12 synthesis among enteric bacteria: evidence for loss and reacquisition of a multigene complex. Genetics 1996, 142:11-24.
25. Leutbecher U., BÖCher R., Linder D., Buckel W. Glutamate mutase from Clostridium cochlearium. Eur. J. Biochem. 1992, 205:759-765.
26. Ma Z., Rao Z., Xu L., Liao X., Fang H., Zhuge B., Zhuge J. Expression of dha operon required for 1,3-PD formation in Escherichia coli and Saccharomyces cerevisiae. Curr. Microbiol. 2010, 60:191-198.
27. Padovani D., Banerjee R. Assembly and protection of the radical enzyme, methylmalonyl-CoA mutase, by its chaperone. Biochemistry 2006, 45:9300-9306.
28. Pharkya P., Burgard A.P., Maranas C.D. Exploring the overproduction of amino acids using the bilevel optimization framework OptKnock. Biotechnol. Bioeng. 2003, 84:887-899.
29. Przystalowska H., Zeyland J., Szymanowska-Powalowska D., Szalata M., Slomski R., Lipinski D. 1,3-Propanediol production by new recombinant Escherichia coli containing genes from pathogenic bacteria. Microbiol. Res. 2015, 171:1-7.
30. Raj H., Szymanski W., de Villiers J., Rozeboom H.J., Veetil V.P., Reis C.R., de Villiers M., Dekker F.J., de Wildeman S., Quax W.J., Thunnissen A.M., Feringa B.L., Janssen D.B., Poelarends G.J. Engineering methylaspartate ammonia lyase for the asymmetric synthesis of unnatural amino acids. Nat. Chem. 2012, 4:478-484.
31. Raj H., Weiner B., Veetil V.P., Reis C.R., Quax W.J., Janssen D.B., Feringa B.L., Poelarends G.J. Alteration of the diastereoselectivity of 3-methylaspartate ammonia lyase by using structure-based mutagenesis. Chembiochem 2009, 10:2236-2245.
32. Roth J.R., Lawrence J.G., Bobik T.A. Cobalamin (coenzyme B12): synthesis and biological significance. Annu. Rev. Microbiol. 1996, 50:137-181.
33. Roymoulik I., Chen H.P., Marsh E.N. The reaction of the substrate analog 2-ketoglutarate with adenosylcobalamin-dependent glutamate mutase. J. Biol. Chem. 1999, 274:11619-11622.
34. Saxena R.K., Anand P., Saran S., Isar J. Microbial production of 1,3-propanediol: recent developments and emerging opportunities. Biotechnol. Adv. 2009, 27:895-913.
35. Suh S.J., Escalante-Semerena J.C. Cloning, sequencing and overexpression of cobA which encodes ATP:corrinoid adenosyltransferase in Salmonella typhimurium. Gene 1993, 129:93-97.
36. Tobimatsu T., Kajiura H., Yunoki M., Azuma M., Toraya T. Identification and expression of the genes encoding a reactivating factor for adenosylcobalamin-dependent glycerol dehydratase. J. Bacteriol. 1999, 181:4110-4113.
37. Toraya T. Radical catalysis in coenzyme B12-dependent isomerization (eliminating) reactions. Chem. Rev. 2003, 103:2095-2127.
38. Toraya T., Mori K. A reactivating factor for coenzyme B12-dependent diol dehydratase. J. Biol. Chem. 1999, 274:3372-3377.
39. Uzum O.B., Karadag E. Equilibrium swelling studies of highly swollen acrylamide/mesaconic acid hydrogels. J. Appl. Polym. Sci. 2005, 96:2253-2259.
40. Uzum O.B., Karadag E. Synthetic polymeric absorbent for dye based on chemically crosslinked acrylamide/mesaconic acid hydrogels. J. Appl. Polym. Sci. 2006, 101:405-413.
41. Wachsman J.T. The role of alpha-ketoglutarate and mesaconate in glutamate fermentation by Clostridium tetanomorphum. J. Biol. Chem. 1956, 223:19-27.
42. Walker G.A., Murphy S., Huennekens F.M. Enzymatic conversion of vitamin B12 to adenosyl-B12: evidence for the existence of two separate reducing systems. Arch. Biochem. Biophys. 1969, 134:95-102.
43. Wang F., Qu H., Zhang D., Tian P., Tan T. Production of 1,3-propanediol from glycerol by recombinant E. coli using incompatible plasmids system. Mol. Biotechnol. 2007, 37:112-119.
44. Zelder O., Beatrix B., Buckel W. Cloning, sequencing and expression in Escherichia coli of the gene encoding component S of the coenzyme B12-dependent glutamate mutase from Clostridium cochlearium. FEMS Microbiol. Lett. 1994, 118:15-21.
45. Zelder O., Beatrix B., Leutbecher U., Buckel W. Characterization of the coenzyme-B12-dependent glutamate mutase from Clostridium cochlearium produced in Escherichia coli. Eur. J. Biochem. 1994, 226:577-585.