Expression of an acetyl-CoA synthase and a CoA-transferase in Escherichia coli to produce modified taxanes in vivo

Biotechnology Journal

Volumn 2, Issue 2, 2007, Pages 266-274

  Loncaric, Catherine ^a   Ward, Amanda F ^a   Walker, Kevin D ^a  

^a Michigan State University   (United States)

Author keywords

Acetoacetate:acetyl CoA CoA transferase of the ato operon; Acetyl CoA synthase; Baccatin III; Paclitaxel; Second generation taxanes

Indexed keywords

10 BUTYRYLBACCATIN III; 10 DEACETYL 10 PROPIONYLBACCATIN III; 10 DEACETYLBACCATIN III; 10 DEACETYLBACCATIN III 10BETA O ACETYLTRANSFERASE; ACETIC ACID; ACETYL COENZYME A SYNTHASE; ACETYL COENZYME A TRANSFERASE; BACCATIN III; BACTERIAL ENZYME; BUTYRIC ACID; BUTYRYLBACCATIN III; FURANYL DERIVATIVE; NATURAL PRODUCT; PACLITAXEL; PROPIONIC ACID; TAXANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CHROMOSOME; BIOTRANSFORMATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CULTURE MEDIUM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVATION; ENZYME ENGINEERING; ESCHERICHIA COLI; GENETIC CODE; IN VIVO STUDY; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION;

ALKALOIDS; BUTYRATES; COENZYME A LIGASES; COENZYME A-TRANSFERASES; ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; GENE EXPRESSION REGULATION, ENZYMOLOGIC; MOLECULAR STRUCTURE; SUBSTRATE SPECIFICITY; TAXOIDS;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; TAXUS;

EID: 34248327919     PISSN: 18606768     EISSN: None     Source Type: Journal    
DOI: 10.1002/biot.200600194     Document Type: Article

References (32)

1. Kumari, S., Simel, E. J., Wolfe, A. J., s70 is the principal sigma factor responsible for transcription of acs, which encodes acetyl coenzyme A synthetase in Escherichia coli. J. Bacteriol. 2000, 182, 551-554.
2. Takamura, Y., Nomura, G., Changes in the intracellular concentration of acetyl-CoA and malonyl-CoA in relation to the carbon and energy metabolism of Escherichia coli K12. J. Gen. Microbiol. 1988, 134, 2249-2253.
3. Wolfe, A. J., The acetate switch. Microbiol. Mol. Biol. Rev. 2005, 69, 12-50.
4. Brock, M., Maerker, C., Schutz, A., Volker, U., et al.., Oxidation of propionate to pyruvate in Escherichia coli: Involvement of methylcitrate dehydratase and aconitase. Eur. J. Biochem. 2002, 269, 6184-6194.
5. Polen, T., Rittmann, D., Wendisch, V. F., Sahm, H., DNA microarray analyses of the long-term adaptive response of Escherichia coli to acetate and propionate. Appl. Environ. Microbiol. 2003, 69, 1759-1774.
6. Patel, S. S., Walt, D. R., Substrate specificity of acetyl coenzyme A synthetase. J. Biol. Chem. 1987, 262, 7132-7134.
7. Valentin, H. E., Mitsky, T. A., Mahadeo, D. A., Tran, M. et al., Application of a propionyl coenzyme A synthetase for poly(3-hydroxypropionate-co-3-hydroxybutyrate) accumulation in recombinant Escherichia coil. Appl. Environ. Microbiol. 2000, 66, 5253-5258.
8. Loncaric, C., Merriweather, E., Walker, K. D., Profiling a Taxol pathway 10β-acetyltransferase: Assessment of the specificity and the production of baccatin III by in vivo acetylation in E. coli. Chem. Biol. 2006, 13, 1-9.
9. Baloglu, E., Hoch, J. M., Chatterjee, S. K., Ravindra, R. et al., Synthesis and biological evaluation of C-3′NH/C-10 and C-2/C-10 modified paclitaxel analogues. Bioorg. Med. Chem. 2003, 11, 1557-1568.
10. Rice, A., Liu, Y., Michaelis, M. L., Himes, R. H. et al., Chemical modification of paclitaxel (Taxol) reduces p-glycoprotein interactions and increases permeation across the blood-brain barrier in vitro and in situ. J. Med. Chem. 2005, 48, 832-838.
11. Choong Cliff, K., Phan, L., Massetti, P., Haddad Fabio, J. et al., Prolongation of patency of airway bypass stents with use of drug-eluting stents. J. Thorac. Cardiovasc. Surg. 2006, 131, 60-64.
12. Boutte, A. M., Neely, M. D., Bird, T. D., Montine, K. S. et al., Diminished Taxol/GTP-stimulated tubulin polymerization in diseased region of brain from patients with late-onset or inherited Alzheimer's disease or frontotemporal dementia with parkinsonism linked to chromosome-17 but not individuals with mild cognitive impairment. J. Alzheimers Dis. 2005, 8, 1-6.
13. Turner, J. E., Greville, K., Murphy, E. C., Hooks, M. A., Characterization of Arabidopsis fluoroacetate-resistant mutants reveals the principal mechanism of acetate activation for entry into the glyoxylate cycle. J. Biol. Chem. 2005, 280, 2780-2787.
14. Campbell, J. W., Morgan-Kiss, R. M., Cronan, J. E., A new Escherichia coli metabolic competency: Growth on fatty acids by a novel anaerobic β-oxidation pathway. Mol. Microbiol. 2003, 47, 793-805.
15. Dagert, M., Ehrlich, S. D., Prolonged incubation in calcium chloride improves the competence of Escherichia coli cells. Gene 1979, 6, 23-38.
16. Dittrich, C. R., Vadali, R. V., Bennett, G. N., San, K.-Y., Redistribution of metabolic fluxes in the central aerobic metabolic pathway of E. coli mutant strains with deletion of the acka-pta and poxb pathways for the synthesis of isoamyl acetate. Biotechnol. Prog. 2005, 21, 627-631.
17. Walker, K., Croteau, R., Taxol biosynthesis: Molecular cloning of a benzoyl-CoA:taxane 2α-O-benzoyltransferase cDNA from Taxus and functional expression in Escherichia coli. Proc. Natl. Acad. Sci. USA 2000, 97, 13591-13596.
18. Kennedy, J., Murli, S., Kealey, J. T., 6-Deoxyerythronolide B analogue production in Escherichia coli through metabolic pathway engineering. Biochemistry 2003, 42, 14342-14348.
19. Pauli, G., Overath, P., ato operon: a highly inducible system for acetoacetate and butyrate degradation in Escherichia coil. Eur. J. Biochem. 1972, 29, 553-562.
20. Walker, K., Croteau, R., Molecular cloning of a 10-deacetylbaccatin III-10-O-acetyl transferase cDNA from Taxus and functional expression in Escherichia coli. Proc. Natl. Acad. Sci. USA 2000, 97, 583-587.
21. Kumari, S., Tishel, R., Eisenbach, M., Wolfe, A. J., Cloning, characterization, and functional expression of acs, the gene which encodes acetyl coenzyme A synthetase in Escherichia coli. J. Bacteriol. 1995, 177, 2878-2886.
22. Kumari, S., Beatty, C. M., Browning, D. F., Busby, S. J. W. et al., Regulation of acetyl coenzyme A synthetase in Escherichia coli. J. Bacteriol. 2000, 182, 4173-4179.
23. Caspi, R., Foerster, H., Fulcher, C. A., Hopkinson, R. et al., MetaCyc: A multiorganism database of metabolic pathways and enzymes. Nucleic Acids Res. 2006, 34, D511-516.
24. Diez-Gonzalez, F., Russell, J., The ability of Escherichia coli O157:H7 to decrease its intracellular pH and resist the toxicity of acetic acid. Microbiology 1997, 143, 1175-1180.
25. Duncan, S. H., Barcenilla, A., Stewart, C. S., Pryde, S. E. et al., Acetate utilization and butyryl coenzyme A (CoA):acetate-CoA transferase in butyrate-producing bacteria from the human large intestine. Appl. Environ. Microbiol. 2002, 68, 5186-5190.
26. Karlsson, S., Lindberg, A., Norin, E., Burman, L. G. et al., Toxins, butyric acid, and other short-chain fatty acids are coordinately expressed and down-regulated by cysteine in Clostridium difficile. Infect. Immun. 2000, 68, 5881-5888.
27. Kapatral, V., Anderson, I., Ivanova, N., Reznik, G. et al., Genome sequence and analysis of the oral bacterium Fusobacterium nucleatum strain ATCC 25586. J. Bacteriol. 2002, 184, 2005-2018.
28. Reed, J., Vo, T., Schilling, C., Palsson, B., An expanded genome-scale model of Escherichia coli K-12 (iJR904 GSM/GPR). Genome Biol. 2003, 4, R54.
29. Sramek, S. J., Frerman, F. E., Escherichia coli coenzyme A-transferase: kinetics, catalytic pathway and structure. Arch. Biochem. Biophys. 1975, 171, 27-35.
30. Bommarus, A. S., Polizzi, K. M., Novel biocatalysts: Recent developments. Chem. Eng. Sci. 2005, 61, 1004-1016.
31. Xie, D., Shao, Z., Achkar, J., Zha, W. et al., Microbial synthesis of triacetic acid lactone. Biotechnol. Bioeng. 2006, 93, 727-736.
32. Smolke, C. D., Martin, V. J. J., Keasling, J. D., Tools for metabolic engineering in Escherichia coli, in: Baneyx, F. (Ed.), Protein Expression Technologies. Horizon Scientific Press, Norwich 2004, pp. 149-197.