Mimicking a natural pathway for de novo biosynthesis: Natural vanillin production from accessible carbon sources

Scientific Reports

Volumn 5, Issue , 2015, Pages

  Ni, Jun ^a   Tao, Fei ^a   Du, Huaiqing ^a   Xu, Ping ^a  

^a Shanghai Jiao Tong University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1-PHENYLPROPANOL; BENZALDEHYDE DERIVATIVE; CARBON; COUMARIC ACID; FERULIC ACID; PROPANOL; VANILLIN;

BIOSYNTHESIS; CHEMISTRY; DRUG EFFECTS; ESCHERICHIA COLI; FERMENTATION; GENE EXPRESSION REGULATION; GENETIC RECOMBINATION; GENETIC TRANSCRIPTION; GENETICS; MASS SPECTROMETRY; METABOLISM; MULTIGENE FAMILY; PLASMID;

BENZALDEHYDES; BIOSYNTHETIC PATHWAYS; CARBON; COUMARIC ACIDS; ESCHERICHIA COLI; FERMENTATION; GENE EXPRESSION REGULATION, BACTERIAL; MASS SPECTROMETRY; MULTIGENE FAMILY; PLASMIDS; PROPANOLS; RECOMBINATION, GENETIC; TRANSCRIPTION, GENETIC;

EID: 84940879312     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep13670     Document Type: Article

References (43)

1. Priefert, H., Rabenhorst, J. & Steinbuchel, A. Biotechnological production of vanillin. Appl. Microbiol. Biotechnol. 56, 296-314 (2001).
2. Brochado, A. R. et al. Improved vanillin production in baker's yeast through in silico design. Microb. Cell Fact. 9, 84-98 (2010).
3. Walton, N. J., Narbad, A., Faulds, C. B. & Williamson, G. Novel approaches to the biosynthesis of vanillin. Curr. Opin. Biotechnol. 11, 490-496 (2000).
4. Muheim, A. & Lerch, K. Towards a high-yield bioconversion of ferulic acid to vanillin. Appl. Microbiol. Biotechnol. 51, 456-461 (1999).
5. Overhage, J., Steinbuchel, A. & Priefert, H. Highly efficient biotransformation of eugenol to ferulic acid and further conversion to vanillin in recombinant strains of Escherichia coli. Appl. Environ. Microbiol. 69, 6569-6576 (2003).
6. Hua, D. L. et al. Biotransformation of isoeugenol to vanillin by a newly isolated Bacillus pumilusstrain: identification of major metabolites. J. Biotechnol. 130, 463-470 (2007).
7. Masai, E. et al. Cloning and characterization of the ferulic acid catabolic genes of Sphingomonas paucimobilis SYK-6. Appl. Environ. Microbiol. 68, 4416-4424 (2002).
8. US Census Bureau. Foreign trade statistics, US Census Bureau, Washington, DC. (2004).
9. Li, K. & Frost, J. W. Synthesis of vanillin from glucose. J. Am. Chem. Soc. 120, 10545-10546 (1998).
10. Hansen, E. H. et al. De novo biosynthesis of vanillin in Fission Yeast (Schizosaccharomyces pombe) and Baker's Yeast (Saccharomyces cerevisiae). Appl. Environ. Microbiol. 75, 2765-2774 (2009).
11. Brochado, A. R. et al. Improved vanillin production in baker's yeast through in silico design. Microb. Cell Fact. 9, 84-98 (2010).
12. Kaur, B. & Chakraborty, D. Biotechnological and molecular approaches for vanillin production: a review. Appl. Biochem. Biotechnol. 169, 1353-1372 (2013).
13. Kunjapur, A. M., Tarasova, Y. & Prather, K. L. Synthesis and accumulation of aromatic aldehydes in an engineered strain of Escherichia coli. J. Am. Chem. Soc. 136, 11644-11654 (2014).
14. Dixon, R. A. et al. The phenylpropanoid pathway and plant defence, a genomics perspective. Mol. Plant Pathol. 3, 371-390 (2002).
15. Gallage, N. J. et al. Vanillin formation from ferulic acid in Vanilla planifolia is catalysed by a single enzyme. Nat. Commun. 5, 4037 (2014).
16. Zhang, H. R. & Stephanopoulos, G. Engineering E. coli for caffeic acid biosynthesis from renewable sugars. Appl. Microbiol. Biotechnol. 97, 3333-3341 (2013).
17. Kang, S. Y. et al. Artificial biosynthesis of phenylpropanoic acids in a tyrosine overproducing Escherichia coli strain. Microb. Cell Fact. 11, 153-161 (2012).
18. Huang, Q., Lin, Y. H. & Yan, Y. J. Caffeic acid production enhancement by engineering a phenylalanine over-producing Escherichia coli strain. Biotechnol. Bioeng. 110, 3188-3196 (2013).
19. Santos, C. N., Koffas, M. & Stephanopoulos, G. Optimization of a heterologous pathway for the production of flavonoids from glucose. Metab. Eng. 13, 392-400 (2011).
20. Kyndt, J. A., Meyer, T. E., Cusanovich, M. A. & Beeumen, Van. J. J. Characterization of a bacterial tyrosine ammonia lyase, a biosynthetic enzyme for the photoactive yellow protein. FEBS Lett. 512, 240-244 (2002).
21. Berner, M. et al. Genes and enzymes involved in caffeic acid biosynthesis in the actinomycete Saccharothrix espanaensis. J. Bacteriol. 188, 2666-2673 (2006).
22. Watts, K. T., Lee, P. C. & Schmidt-Dannert, C. Exploring recombinant flavonoid biosynthesis in metabolically engineered Escherichia coli. Chembiochem 5, 500-507 (2004).
23. Kim, Y. H. et al. Gene engineering, purification, crystallization and preliminary X-ray diffraction of cytochrome P450 pcoumarate-3-hydroxylase (C3H), the Arabidopsis membrane protein. Protein Expres. Purif. 79, 149-155 (2011).
24. Lin, Y. & Yan, Y. Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex. Microb. Cell Fact. 11, 42-50 (2012).
25. Choi, O. et al. Biosynthesis of plant-specific phenylpropanoids by construction of an artificial biosynthetic pathway in Escherichia coli. J. Ind. Microbiol. Biotechnol. 38, 1657-1665 (2011).
26. Yang, W. W. et al. Characterization of two Streptomyces enzymes that convert ferulic acid to vanillin. PLoS One, 8, e67339. (2013).
27. Nakagawa, A. et al. A bacterial platform for fermentative production of plant alkaloids. Nat. Commun. 2, 326-333 (2011).
28. Xue, Y., Zhang, Y., Grace, S. & He, Q. Functional expression of an Arabidopsis p450 enzyme, p-coumarate-3-hydroxylase, in the cyanobacterium Synechocystis PCC 6803 for the biosynthesis of caffeic acid. J. Appl. Phycol. 26, 219-226 (2014).
29. Kim, S. & Lee, S. B. Rare codon clusters at 5?-end influence heterologous expression of archaeal gene in Escherichia coli. Protein Expres. Purif. 50, 49-57 (2006).
30. Muñoz, A. J. et al. Metabolic engineering of Escherichia coli for improving L-3, 4-dihydroxyphenylalanine (L-DOPA) synthesis from glucose. J. Ind. Microbiol Biot. 38, 1845-1852 (2011).
31. Ahn, J. O. et al. Exploring the effects of carbon sources on the metabolic capacity for shikimic acid production in Escherichia coli using in silico metabolic predictions. J. Microbiol. Biotechnol. 18, 1773-1784 (2008).
32. Serrano, L. Synthetic Biology: Promises and Challenges. Mol. Syst. Biol. 3, 158-162 (2007).
33. Andrianantoandro, E., Basu, S., Karig, D. K. & Weiss, R. Synthetic biology: new engineering rules for an emerging discipline. Mol. Syst. Biol. 2, 1-14 (2006).
34. Goossens, A. et al. A functional genomics approach toward the understanding of secondary metabolism in plant cells. Proc. Natl. Acad. Sci. USA 100, 8595-8600 (2003).
35. Ikeda, M. & Katsumata, R. Metabolic engineering to produce tyrosine or phenylalanine in a tryptophan-producing Corynebacterium glutamicum strain. Appl. Environ. Microbiol. 58, 781-785 (1992).
36. Bongaerts, J., Krämer, M., Müller, U., Raeven, L. & Wubbolts, M. Metabolic engineering for microbial production of aromatic amino acids and derived compounds. Metab. Eng. 3, 289-300 (2001).
37. Lütke-Eversloh, T. & Stephanopoulos, G. Combinatorial pathway analysis for improved l-tyrosine production in Escherichia coli: Identification of enzymatic bottlenecks by systematic gene overexpression. Metab. Eng. 10, 69-77 (2008).
38. Lee, W. H., Park, J. B., Park, K., Kim, M. D. & Seo, J. H. Enhanced production of ?-caprolactone by overexpression of NADPHregenerating glucose 6-phosphate dehydrogenase in recombinant Escherichia coli harboring cyclohexanone monooxygenase gene. Appl. Microbiol. Biotechnol. 76, 329-338 (2007).
39. Johannes, T. W., Woodyer, R. D. & Zhao, H. Efficient regeneration of NADPH using an engineered phosphite dehydrogenase. Biotechnol. Bioeng. 96, 18-26 (2007).
40. Xu, Y. Q. et al. Systematic metabolic engineering of Escherichia coli for high-yield production of fuel bio-chemical 2,3-butanediol. Metab. Eng. 23, 22-23 (2014).
41. Mehta, V. J., Thumar, J. T. & Singh, S. P. Production of alkaline protease from an alkaliphilic actinomycete. Bioresour. Technol. 97, 1650-1654 (2006).
42. Binder, J. B. & Raines, R. T. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J. Am. Chem. Soc. 131, 1979-1985 (2009).
43. Hoover, D. M. & Lubkowski, J. DNA Works: an automated method for designing oligonucleotides for PCR-based gene synthesis. Nucleic Acids Res. 30, e43 (2002).