A Novel Synthetic Pathway Enables Microbial Production of Polyphenols Independent from the Endogenous Aromatic Amino Acid Metabolism

ACS Synthetic Biology

Volumn 6, Issue 3, 2017, Pages 410-415

  Kallscheuer, Nicolai ^a   Vogt, Michael ^a   Marienhagen, Jan ^a  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

Corynebacterium glutamicum; phenylpropanoids; plant secondary metabolites; resveratrol; reverse oxidation

Indexed keywords

4 HYDROXYBENZOIC ACID; AMMONIA LYASE; AROMATIC AMINO ACID; BENZOIC ACID DERIVATIVE; POLYPHENOL; RESVERATROL; STILBENE DERIVATIVE; 4 HYDROXYBENZOIC ACID ESTER; 4-HYDROXYBENZOIC ACID;

AMINO ACID METABOLISM; AMINO ACID SYNTHESIS; BACTERIAL STRAIN; CORYNEBACTERIUM GLUTAMICUM; FATTY ACID OXIDATION; LETTER; PRIORITY JOURNAL; REACTION ANALYSIS; THERMODYNAMICS; BIOCHEMISTRY; BIOTECHNOLOGY; METABOLIC ENGINEERING; METABOLISM; PHYSIOLOGY; PLANT; PROCEDURES;

AMINO ACIDS, AROMATIC; BENZOATES; BIOCHEMICAL PHENOMENA; BIOTECHNOLOGY; CORYNEBACTERIUM GLUTAMICUM; METABOLIC ENGINEERING; PARABENS; PLANTS; POLYPHENOLS; THERMODYNAMICS;

EID: 85017657564     PISSN: None     EISSN: 21615063     Source Type: Journal    
DOI: 10.1021/acssynbio.6b00291     Document Type: Letter

References (37)

1. Seigler, D. S. ( 2012 ) Plant Secondary Metabolism; Springer Science & Business Media.
2. Tissier, A., Ziegler, J., and Vogt, T. ( 2014 ) Specialized Plant Metabolites: Diversity and Biosynthesis, In Ecological Biochemistry, pp 14-37, Wiley-VCH Verlag GmbH & Co. KGaA.
3. Manach, C., Scalbert, A., Morand, C., Rémésy, C., and Jiménez, L. ( 2004 ) Polyphenols: food sources and bioavailability Am. J. Clin. Nutr. 79, 727-747
4. Spatafora, C. and Tringali, C. ( 2012 ) Natural-derived polyphenols as potential anticancer agents Anti-Cancer Agents Med. Chem. 12, 902-918 10.2174/187152012802649996
5. Jangaard, N. O. ( 1974 ) The characterization of phenylalanine ammonia-lyase from several plant species Phytochemistry 13, 1765-1768 10.1016/0031-9422(74)85086-7
6. Tropf, S., Kärcher, B., Schröder, G., and Schröder, J. ( 1995 ) Reaction Mechanisms of Homodimeric Plant Polyketide Synthases (Stilbene and Chalcone Synthase): A single active site for the condensing reactions is sufficient for the synthesis of stilbenes, chalcones and 6′-deoxychalcones J. Biol. Chem. 270, 7922-7928 10.1074/jbc.270.14.7922
7. Marienhagen, J. and Bott, M. ( 2013 ) Metabolic engineering of microorganisms for the synthesis of plant natural products J. Biotechnol. 163, 166-178 10.1016/j.jbiotec.2012.06.001
8. Lim, C. G., Fowler, Z. L., Hueller, T., Schaffer, S., and Koffas, M. A. ( 2011 ) High-yield resveratrol production in engineered Escherichia coli Appl. Environ. Microbiol. 77, 3451-3460 10.1128/AEM.02186-10
9. Koopman, F., Beekwilder, J., Crimi, B., van Houwelingen, A., Hall, R. D., Bosch, D., van Maris, A. J., Pronk, J. T., and Daran, J.-M. ( 2012 ) De novo production of the flavonoid naringenin in engineered Saccharomyces cerevisiae Microb. Cell Fact. 11, 155 10.1186/1475-2859-11-155
10. van Summeren-Wesenhagen, P. V. and Marienhagen, J. ( 2015 ) Metabolic engineering of Escherichia coli for the synthesis of the plant polyphenol pinosylvin Appl. Environ. Microbiol. 81, 840-849 10.1128/AEM.02966-14
11. Kallscheuer, N., Vogt, M., Stenzel, A., Gätgens, J., Bott, M., and Marienhagen, J. ( 2016 ) Construction of a Corynebacterium glutamicum platform strain for the production of stilbenes and (2S)-flavanones Metab. Eng. 38, 47-55 10.1016/j.ymben.2016.06.003
12. Kallscheuer, N., Vogt, M., Kappelmann, J., Krumbach, K., Noack, S., Bott, M., and Marienhagen, J. ( 2016 ) Identification of the phd gene cluster responsible for phenylpropanoid utilization in Corynebacterium glutamicum Appl. Microbiol. Biotechnol. 100, 1871-1881 10.1007/s00253-015-7165-1
13. Becker, J. and Wittmann, C. ( 2012 ) Bio-based production of chemicals, materials and fuels - Corynebacterium glutamicum as versatile cell factory Curr. Opin. Biotechnol. 23, 631-640 10.1016/j.copbio.2011.11.012
14. Eudes, A., Juminaga, D., Baidoo, E. E., Collins, F. W., Keasling, J. D., and Loqué, D. ( 2013 ) Production of hydroxycinnamoyl anthranilates from glucose in Escherichia coli Microb. Cell Fact. 12, 62 10.1186/1475-2859-12-62
15. Lin, Y. and Yan, Y. ( 2012 ) Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex Microb. Cell Fact. 11, 42 10.1186/1475-2859-11-42
16. Zhou, S., Liu, P., Chen, J., Du, G., Li, H., and Zhou, J. ( 2016 ) Characterization of mutants of a tyrosine ammonia-lyase from Rhodotorula glutinis Appl. Microbiol. Biotechnol. 100, 10443 10.1007/s00253-016-7672-8
17. Trautwein, K., Wilkes, H., and Rabus, R. ( 2012 ) Proteogenomic evidence for β-oxidation of plant-derived 3-phenylpropanoids in “Aromatoleum aromaticum” EbN1 Proteomics 12, 1402-1413 10.1002/pmic.201100279
18. Dellomonaco, C., Clomburg, J. M., Miller, E. N., and Gonzalez, R. ( 2011 ) Engineered reversal of the β-oxidation cycle for the synthesis of fuels and chemicals Nature 476, 355-359 10.1038/nature10333
19. Wöhlbrand, L., Kallerhoff, B., Lange, D., Hufnagel, P., Thiermann, J., Reinhardt, R., and Rabus, R. ( 2007 ) Functional proteomic view of metabolic regulation in “Aromatoleum aromaticum” strain EbN1 Proteomics 7, 2222-2239 10.1002/pmic.200600987
20. Haapalainen, A. M., Meriläinen, G., and Wierenga, R. K. ( 2006 ) The thiolase superfamily: condensing enzymes with diverse reaction specificities Trends Biochem. Sci. 31, 64-71 10.1016/j.tibs.2005.11.011
21. Clomburg, J. M., Vick, J. E., Blankschien, M. D., Rodríguez-Moyá, M., and Gonzalez, R. ( 2012 ) A synthetic biology approach to engineer a functional reversal of the β-oxidation cycle ACS Synth. Biol. 1, 541-554 10.1021/sb3000782
22. Caspi, R., Billington, R., Ferrer, L., Foerster, H., Fulcher, C. A., Keseler, I. M., Kothari, A., Krummenacker, M., Latendresse, M., and Mueller, L. A. ( 2016 ) The MetaCyc database of metabolic pathways and enzymes and the BioCyc collection of pathway/genome databases Nucleic Acids Res. 44, D471-D480 10.1093/nar/gkv1164
23. Modis, Y. and Wierenga, R. K. ( 1999 ) A biosynthetic thiolase in complex with a reaction intermediate: the crystal structure provides new insights into the catalytic mechanism Structure 7, 1279-1290 10.1016/S0969-2126(00)80061-1
24. Pátek, M., Holátko, J., Busche, T., Kalinowski, J., and Nešvera, J. ( 2013 ) Corynebacterium glutamicum promoters: a practical approach Microb. Biotechnol. 6, 103-117 10.1111/1751-7915.12019
25. Chaudhry, M. T., Huang, Y., Shen, X.-H., Poetsch, A., Jiang, C.-Y., and Liu, S.-J. ( 2007 ) Genome-wide investigation of aromatic acid transporters in Corynebacterium glutamicum Microbiology 153, 857-865 10.1099/mic.0.2006/002501-0
26. Agnihotri, G. and Liu, H.-w. ( 2003 ) Enoyl-CoA hydratase: Reaction, mechanism, and inhibition Bioorg. Med. Chem. 11, 9-20 10.1016/S0968-0896(02)00333-4
27. Noyes, B. E., Glatthaar, B. E., Garavelli, J. S., and Bradshaw, R. A. ( 1974 ) Structural and Functional Similarities Between Mitochondrial Malate Dehydrogenase and l-3-Hydroxyacyl CoA Dehydrogenase Proc. Natl. Acad. Sci. U. S. A. 71, 1334-1338 10.1073/pnas.71.4.1334
28. Clomburg, J. M., Blankschien, M. D., Vick, J. E., Chou, A., Kim, S., and Gonzalez, R. ( 2015 ) Integrated engineering of β-oxidation reversal and ω-oxidation pathways for the synthesis of medium chain ω-functionalized carboxylic acids Metab. Eng. 28, 202-212 10.1016/j.ymben.2015.01.007
29. Babu, T., Yun, E. J., Kim, S., Kim, D. H., Liu, K. H., Kim, S. R., and Kim, K. H. ( 2015 ) Engineering Escherichia coli for the production of adipic acid through the reversed β-oxidation pathway Process Biochem. 50, 2066-2071 10.1016/j.procbio.2015.09.018
30. Gulevich, A. Y., Skorokhodova, A. Y., Sukhozhenko, A. V., Shakulov, R. S., and Debabov, V. G. ( 2012 ) Metabolic engineering of Escherichia coli for 1-butanol biosynthesis through the inverted aerobic fatty acid β-oxidation pathway Biotechnol. Lett. 34, 463-469 10.1007/s10529-011-0797-z
31. Bertani, G. ( 1951 ) Studies on Lysogenesis I: The Mode of Phage Liberation by Lysogenic Escherichia coli J. Bacteriol. 62, 293
32. Keilhauer, C., Eggeling, L., and Sahm, H. ( 1993 ) Isoleucine synthesis in Corynebacterium glutamicum: molecular analysis of the ilvB-ilvN-ilvC operon J. Bacteriol. 175, 5595-5603 10.1128/jb.175.17.5595-5603.1993
33. Sambrook, J. and Russell, D. ( 2001 ) Molecular Cloning, Vol. 1-3, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
34. Eggeling, L. and Bott, M. ( 2005 ) Handbook of Corynebacterium glutamicum; CRC Press.
35. Engler, C., Gruetzner, R., Kandzia, R., and Marillonnet, S. ( 2009 ) Golden gate shuffling: a one-pot DNA shuffling method based on type IIs restriction enzymes PLoS One 4, e5553 10.1371/journal.pone.0005553
36. Kortmann, M., Kuhl, V., Klaffl, S., and Bott, M. ( 2015 ) A chromosomally encoded T7 RNA polymerase-dependent gene expression system for Corynebacterium glutamicum: construction and comparative evaluation at the single-cell level Microb. Biotechnol. 8, 253-265 10.1111/1751-7915.12236
37. Gande, R., Dover, L. G., Krumbach, K., Besra, G. S., Sahm, H., Oikawa, T., and Eggeling, L. ( 2007 ) The two carboxylases of Corynebacterium glutamicum essential for fatty acid and mycolic acid synthesis J. Bacteriol. 189, 5257-5264 10.1128/JB.00254-07