Artificial de novo biosynthesis of hydroxystyrene derivatives in a tyrosine overproducing Escherichia coli strain

Microbial Cell Factories

Volumn 14, Issue 1, 2015, Pages

  Kang, Sun Young ^a,b   Choi, Oksik ^a   Lee, Jae Kyoung ^a,b   Ahn, Jung Oh ^a   Ahn, Jong Seog ^a   Hwang, Bang Yeon ^b   Hong, Young Soo ^a  

^a Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^b Chungbuk National University   (South Korea)

Author keywords

3,4 Dihydroxystyrene; 4 Hydroxy 3 methoxystyrene; 4 Hydroxystyrene; De novo Biosynthesis

Indexed keywords

3,4 DIHYDROXYSTYRENE; 4 HYDROXY 3 METHOXYSTYRENE; 4 HYDROXYSTYRENE; HYDROXYSTYRENE DERIVATIVE; STYRENE DERIVATIVE; TYROSINE; UNCLASSIFIED DRUG; ESCHERICHIA COLI PROTEIN; HYDROXYSTYRENE-STYRENE; POLYSTYRENE DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; ARTIFICIAL BIOSYNTHETIC PATHWAY; BACILLUS; BACTERIAL GENE; BACTERIAL STRAIN; BACTERIUM CULTURE; BIOSYNTHESIS; CARBON SOURCE; CODON; COM GENE; CONTROLLED STUDY; ESCHERICHIA COLI; NONHUMAN; PHENOLIC ACID BIOSYNTHETIC GENE; PHENOLIC ACID DECARBOXYLASE GENE; PROTEIN EXPRESSION; SAM5 GENE; TAL GENE; GENETIC ENGINEERING; GENETICS; METABOLISM; PROCEDURES;

ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; GENETIC ENGINEERING; POLYSTYRENES; TYROSINE;

EID: 84931056040     PISSN: None     EISSN: 14752859     Source Type: Journal    
DOI: 10.1186/s12934-015-0268-7     Document Type: Article

References (31)

1. Bernini R, Mincione E, Barontini M, Provenzanoa GLS (2007) Obtaining 4-vinylphenols by decarboxylation of natural 4-hydroxycinnamic acids under microwave irradiation. Tetrahedron 63:9663-9667
2. Diao J, Liu H, Wang J, Feng Z, Chen T, Miao C et al (2015) Porous graphene-based material as an efficient metal free catalyst for the oxidative dehydrogenation of ethylbenzene to styrene. Chem Commun 51:3423-3425
3. Keller N, Maksimova NI, Roddatis VV, Schur M, Mestl G, Butenko YV et al (2002) The catalytic use of onion-like carbon materials for styrene synthesis by oxidative dehydrogenation of ethylbenzene. Angew Chem Int Ed Engl 41:1885-1888
4. Claypool JT, Raman DR, Jarboe LR, Nielsen DR (2014) Technoeconomic evaluation of bio-based styrene production by engineered Escherichia coli. J Ind Microbiol Biotechnol 41:1211-1216
5. Qi WW, Vannelli T, Breinig S, Ben-Bassat A, Gatenby AA, Haynie SL et al (2007) Functional expression of prokaryotic and eukaryotic genes in Escherichia coli for conversion of glucose to p-hydroxystyrene. Metab Eng 9:268-276
6. Sariaslani FS (2007) Development of a combined biological and chemical process for production of industrial aromatics from renewable resources. Annu Rev Microbiol 61:51-69
7. McKenna R, Nielsen DR (2011) Styrene biosynthesis from glucose by engineered E. coli. Metab Eng 13:544-554
8. Verhoef S, Wierckx N, Westerhof RG, de Winde JH, Ruijssenaars HJ (2009) Bioproduction of p-hydroxystyrene from glucose by the solvent-tolerant bacterium Pseudomonas putida S12 in a two-phase water-decanol fermentation. Appl Environ Microbiol 75:931-936
9. McKenna R, Thompson B, Pugh S, Nielsen DR (2014) Rational and combinatorial approaches to engineering styrene production by Saccharomyces cerevisiae. Microb Cell Fact 13:123
10. McKenna R, Moya L, McDaniel M, Nielsen DR (2015) Comparing in situ removal strategies for improving styrene bioproduction. Bioprocess Biosyst Eng 38:165-174
11. Adkins J, Pugh S, McKenna R, Nielsen DR (2012) Engineering microbial chemical factories to produce renewable "biomonomers". Front Microbiol 3:313
12. Woolston BM, Edgar S, Stephanopoulos G (2013) Metabolic engineering: past and future. Annu Rev Chem Biomol Eng 4:259-288
13. Jang YS, Kim B, Shin JH, Choi YJ, Choi S, Song CW et al (2012) Bio-based production of C2-C6 platform chemicals. Biotechnol Bioeng 109:2437-2459
14. Lee JW, Na D, Park JM, Lee J, Choi S, Lee SY (2012) Systems metabolic engineering of microorganisms for natural and non-natural chemicals. Nat Chem Biol 8:536-546
15. Barker JL, Frost JW (2001) Microbial synthesis of p-hydroxybenzoic acid from glucose. Biotechnol Bioeng 76:376-390
16. Choi O, Lee JK, Kang SY, Pandey RP, Sohng JK, Ahn JS et al (2014) Construction of artificial biosynthetic pathways for resveratrol glucoside derivatives. J Microbiol Biotechnol 24:614-618
17. Choi O, Wu CZ, Kang SY, Ahn JS, Uhm TB, Hong YS (2011) Biosynthesis of plant-specific phenylpropanoids by construction of an artificial biosynthetic pathway in Escherichia coli. J Ind Microbiol Biotechnol 38:1657-1665
18. Kang SY, Lee JK, Choi O, Kim CY, Jang JH, Hwang BY et al (2014) Biosynthesis of methylated resveratrol analogs through the construction of an artificial biosynthetic pathway in E. coli. BMC Biotechnol 14:67
19. Winkel-Shirley B (2001) Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiol 126:485-493
20. Kang SY, Choi O, Lee JK, Hwang BY, Uhm TB, Hong YS (2012) Artificial biosynthesis of phenylpropanoic acids in a tyrosine overproducing Escherichia coli strain. Microb Cell Fact 11:153
21. Jung DH, Choi W, Choi KY, Jung E, Yun H, Kazlauskas RJ et al (2013) Bioconversion of p-coumaric acid to p-hydroxystyrene using phenolic acid decarboxylase from B. amyloliquefaciens in biphasic reaction system. Appl Microbiol Biotechnol 97:1501-1511
22. Mukai N, Masaki K, Fujii T, Kawamukai M, Iefuji H (2010) PAD1 and FDC1 are essential for the decarboxylation of phenylacrylic acids in Saccharomyces cerevisiae. J Biosci Bioeng 109:564-569
23. Cavin JF, Barthelmebs L, Divies C (1997) Molecular characterization of an inducible p-coumaric acid decarboxylase from Lactobacillus plantarum: gene cloning, transcriptional analysis, overexpression in Escherichia coli, purification, and characterization. Appl Environ Microbiol 63:1939-1944
24. Zhang H, Stephanopoulos G (2013) Engineering E. coli for caffeic acid biosynthesis from renewable sugars. Appl Microbiol Biotechnol 97:3333-3341
25. Lutke-Eversloh T, Stephanopoulos G (2005) Feedback inhibition of chorismate mutase/prephenate dehydrogenase (TyrA) of Escherichia coli: generation and characterization of tyrosine-insensitive mutants. Appl Environ Microbiol 71:7224-7228
26. Salgado JM, Rodriguez-Solana R, Curiel JA, de Las Rivas B, Munoz R, Dominguez JM (2014) Bioproduction of 4-vinylphenol from corn cob alkaline hydrolyzate in two-phase extractive fermentation using free or immobilized recombinant E. coli expressing pad gene. Enzyme Microb Technol 58-59:22-28
27. Salgado JM, Rodriguez-Solana R, Curiel JA, de Las Rivas B, Munoz R, Dominguez JM (2012) Production of vinyl derivatives from alkaline hydrolysates of corn cobs by recombinant Escherichia coli containing the phenolic acid decarboxylase from Lactobacillus plantarum CECT 748T. Bioresour Technol 117:274-285
28. Ramos-Gonzalez MI, Ben-Bassat A, Campos MJ, Ramos JL (2003) Genetic engineering of a highly solvent-tolerant Pseudomonas putida strain for biotransformation of toluene to p-hydroxybenzoate. Appl Environ Microbiol 69:5120-5127
29. Coghe S, Benoot K, Delvaux F, Vanderhaegen B, Delvaux FR (2004) Ferulic acid release and 4-vinylguaiacol formation during brewing and fermentation: indications for feruloyl esterase activity in Saccharomyces cerevisiae. J Agric Food Chem 52:602-608
30. Lutke-Eversloh T, Stephanopoulos G (2007) L-tyrosine production by deregulated strains of Escherichia coli. Appl Microbiol Biotechnol 75:103-110
31. Miroux B, Walker JE (1996) Over-production of proteins in Escherichia coli: mutant hosts that allow synthesis of some membrane proteins and globular proteins at high levels. J Mol Biol 260:289-298