Improved production of triostin A in engineered Escherichia coli with furnished quinoxaline chromophore by design of experiments in small-scale culture

Biotechnology Progress

Volumn 24, Issue 1, 2008, Pages 134-139

  Praseuth, Alex P ^a   Praseuth, Mike B ^b   Oguri, Hiroki ^c   Oikawa, Hideaki ^c   Watanabe, Kenji ^a   Wang, Clay C C ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b CALIFORNIA STATE UNIVERSITY   (United States)

^c HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITUMOR AGENTS; CELL DENSITY; FED-BATCH FERMENTATION;

BIOSYNTHESIS; CARBOXYLIC ACIDS; CELL CULTURE; ESCHERICHIA COLI; LIQUID CHROMATOGRAPHY; MASS SPECTROMETERS;

BODY FLUIDS;

2 QUINOXALINECARBOXYLIC ACID; DRUG DERIVATIVE; ECHINOMYCIN; QUINOMYCIN; QUINOXALINE DERIVATIVE; QUINOXALINE-2-CARBOXYLIC ACID; TRIOSTIN A; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; DRUG EFFECT; ESCHERICHIA COLI; GENE EXPRESSION REGULATION; GENETIC ENGINEERING; GENETICS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM;

CHROMATOGRAPHY, LIQUID; ECHINOMYCIN; ESCHERICHIA COLI; GENE EXPRESSION REGULATION, BACTERIAL; GENETIC ENGINEERING; MASS SPECTROMETRY; MOLECULAR STRUCTURE; QUINOXALINES;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; STREPTOMYCES;

EID: 38949101150     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp070298y     Document Type: Conference Paper

References (23)

1. Schwarzer, D.; Finking, R.; Marahiel, M. A. Nonribosomal peptides: From genes to products. Nat. Prod. Rep. 2003, 20, 275-287.
2. Shuler, M. L. Bioreactor engineering as an enabling technology to tap biodiversity. The case of taxol. Ann. N.Y. Acad. Sci. 1994, 745, 455-461.
3. Steinerova, N.; Lipavska, H.; Stajner, K.; Caslavska, J.; Blumauerova, M.; Cudlin, J.; Vanek, Z. Production of quinomycin A in Streptomyces lasaliensis. Folia Microbiol. (Praha) 1987, 32, 1-5.
4. Boger, D. L.; Ichikawa, S.; Tse, W. C.; Hedrick, M. P.; Jin, Q. Total syntheses of thiocoraline and BE-22179 and assessment of their DNA binding and biological properties. J. Am. Chem. Soc. 2001, 123, 561-568.
5. Cane, D. E.; Walsh, C. T.; Khosla, C. Harnessing the biosynthetic code: combinations, permutations, and mutations. Science 1998, 282, 63-68.
6. Marahiel, M. A.; Stachelhaus, T.; Mootz, H. D. Modular peptide synthetases involved in nonribosomal peptide synthesis. Chem. Rev. 1997, 97, 2651-2674.
7. Schwarzer, D.; Finking, R.; Marahiel, M. A. Nonribosomal peptides: from genes to products. Nat. Prod. Rep. 2003, 20, 275-287.
8. Kieser, T.; Bibb, M. J.; Buttner, M. J.; Chater, K. F.; Hopwood, D. A. Practical Streptomyces Genetics; The John Innes Foundation: Norwich, England, 2000.
9. Watanabe, K.; Oikawa, H. Robust platform for de novo productions of heterologous polyketides and nonribosomal peptides in Escherichia coli. Org. Biomol. Chem. 2007, 5, 593-602.
10. Pfeifer, B. A.; Admiraal, S. J.; Gramajo, H.; Cane, D. E.; Khosla, C. Biosynthesis of complex polyketides in a metabolically engineered strain of E. coli. Science 2001, 291, 1790-1792.
11. Pfeifer, B. A.; Wang, C. C.; Walsh, C. T.; Khosla, C. Biosynthesis of yersiniabactin, a complex polyketide-nonribosomal peptide, using Escherichia coli as a heterologous host. Appl. Environ. Microbiol. 2003, 69, 6698-6702.
12. Watanabe, K.; Rude, M. A.; Walsh, C. T.; Khosla, C. Engineered biosynthesis of an ansamycin polyketide precursor in Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 9774-9778.
13. Watanabe, K.; Hotta, K.; Praseuth, A. P.; Koketsu, K.; Migita, A.; Boddy, C. N.; Wang, C. C. C.; Oguri, H.; Oikawa, H. Total biosynthesis of antitumor nonribosomal peptides in Escherichia coli. Nature Chem. Biol. 2006, 2, 423-428.
14. Wang, A. H.; Ughetto, G.; Quigley, G. J.; Hakoshima, T.; van der Marel, G. A.; van Boom, J. H.; Rich, A. The molecular structure of a DNA-triostin A complex. Science 1984, 225, 1115-1121.
15. Chen, H.; Patel, D. J. Solution structure of a quinomycin bisintercalator-DNA complex. J. Mol. Biol. 1995, 246, 164-79.
16. Neidle, S.; Pearl, L. H.; Skelly, J. V. DNA structure and perturbation by drug binding. Biochem. J. 1987, 243, 1-13.
17. Furuya, K.; Hutchinson, C. R. The DrrC protein of Streptomyces peucetius, a UvrA-like protein, is a DNA-binding protein whose gene is induced by daunorubicin. FEMS Microbiol. Lett. 1998, 168, 243-249.
18. 15N nuclear magnetic resonance study of the biosynthesis of quinoxaline antibiotics. Biochim. Biophys. Acta 1984, 798, 111-114.
19. Koketsu, K.; Oguri, H.; Watanabe, K.; Oikawa, H. Identification and stereochemical assignment of the β-hydroxytryptophan intermediate in the echinomycin biosynthetic pathway. Org. Lett. 2006, 8, 4719-4722.
20. Sambrook, J.; Russell, D. W. Molecular Cloning, 3rd ed.; Cold Spring Harbor Laboratory Press: New York, 2001.
21. Schmoock, G.; Pfennig, F.; Jewiarz, J.; Schlumbohm, W.; Laubinger, W.; Schauwecker, F.; Keller, U. Functional cross-talk between fatty acid synthesis and nonribosomal peptide synthesis in quinoxaline antibiotic-producing streptomycetes. J. Biol. Chem. 2005, 280, 4339-4349.
22. Lambalot, R. H.; Gehring, A. M.; Flugel, R. S; Zuber, P.; LaCelle, M.; Marahiel, M. A.; Reid, R.; Khosla, C.; Walsh, C. T. A new enzyme superfamily - the phosphopantetheinyl transferases. Chem. Biol. 1996, 3, 923-936.
23. Gauvreau, D.; Waring, M. J.; Directed biosynthesis of novel derivatives of echinomycin by Streptomyces echinatus. I. Effect of exogenous analogues of quinoxaline-2-carboxylic acid on the fermentation. Can. J. Microbiol. 1984, 30, 439-450.