Microbial conversion of glucose to a novel chemical building block, 2-pyrone-4,6-dicarboxylic acid

Metabolic Engineering

Volumn 11, Issue 4-5, 2009, Pages 213-220

  Nakajima, Masahiro ^a   Nishino, Yukari ^a   Tamura, Masatsugu ^a   Mase, Kohei ^a,b   Masai, Eiji ^c   Otsuka, Yuichiro ^d   Nakamura, Masaya ^d   Sato, Kanna ^a   Fukuda, Masao ^c   Shigehara, Kiyotaka ^a   Ohara, Seiji ^d   Katayama, Yoshihiro ^a   Kajita, Shinya ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b TOYOTA INDUSTRIES CORPORATION   (Japan)

^c NAGAOKA UNIVERSITY OF TECHNOLOGY   (Japan)

^d FORESTRY AND FOREST PRODUCTS RESEARCH INSTITUTE   (Japan)

Author keywords

Biomass; Escherichia coli; Glucose; Lignin degradation; Shikimate pathway; Sphingobium

Indexed keywords

ALTERNATIVE SYSTEMS; BIOMASS CROP; CELLULOSIC WASTES; CHEMICAL BUILDING BLOCKS; CONCENTRATION OF; DICARBOXYLIC ACID; E. COLI; HOST STRAIN; LIGNIN DEGRADATION; MICROBIAL CONVERSIONS; NIGER; OPTIMAL CONDITIONS; PROTOCATECHUATE; PSEUDOMONAS PUTIDA; RECOMBINANT E. COLI; RECOMBINANT ESCHERICHIA COLI; SHIKIMATE PATHWAY; SPHINGOBIUM; SPHINGOMONAS PAUCIMOBILIS SYK-6; STARTING MATERIALS; SYNTHETIC POLYMERS;

ACIDS; BIOMASS; CELL CULTURE; DEGRADATION; ESCHERICHIA COLI; GENES; LIGNIN; SUGAR (SUCROSE);

GLUCOSE;

2 PYRONE 4,6 DICARBOXYLIC ACID; DICARBOXYLIC ACID DERIVATIVE; GLUCOSE; GLUCOSE DEGRADATION PRODUCT; SHIKIMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL; ESCHERICHIA COLI; GLYCOLYSIS; LYSOGENIZATION; NONHUMAN; PRIORITY JOURNAL;

BIOTECHNOLOGY; CULTURE MEDIA; ESCHERICHIA COLI; GLUCOSE; MUTATION; PYRONES; SHIKIMIC ACID; SPHINGOMONAS;

ACIDS; BACTERIA; BIOMASS; DEGRADATION; GENES; GLUCOSE; LIGNINS; SUGAR; TISSUE CULTURE;

EMERICELLA; ESCHERICHIA COLI; PSEUDOMONAS PUTIDA; SPHINGOBIUM; SPHINGOMONAS PAUCIMOBILIS;

EID: 68049128095     PISSN: 10967176     EISSN: 10967184     Source Type: Journal    
DOI: 10.1016/j.ymben.2009.02.002     Document Type: Article

References (27)

1. Barker J.L., and Frost J.W. Microbial synthesis of p-hydroxybenzoic acid from glucose. Biotechnol. Bioeng. 76 (2001) 376-390
2. Bongaerts J., Krämer M., Müller U., Raeve L., and Wubbolts M. Metabolic engineering for microbial production of aromatic amino acids and derived compounds. Metab. Eng. 3 (2001) 289-300
3. Draths K.M., Knop D.R., and Frost J.W. Shikimic acid and quinic acid: replacing isolation from plant sources with recombinant microbial biocatalysis. J. Am. Chem. Soc. 121 (1999) 1603-1604
4. Frost J.W., and Draths K.M. Biocatalytic synthesis of aromatic from d-glucose. Annu. Rev. Microbiol. 49 (1995) 557-579
5. Hawkins A.R., Dasilva A.J.F., and Roberts C.F. Cloning and characterization of the three enzyme structural genes QUTB, QUTC and QUTE from the quinic acid utilization gene-cluster in Aspergillus nidulans. Curr. Genet. 9 (1985) 305-311
6. Ikeda M. Towards bacterial strains overproducing l-tryptophan and other aromatics by metabolic engineering. Appl. Microbiol. Biotechnol. 69 (2006) 615-626
7. Jensen R.A., and Nasser D.S. Comparative regulation of isoenzymic 3-deoxy-d-arabino-heptulosonate 7-phosphate synthetases in microorganisms. J. Bacteriol. 95 (1968) 188-196
8. Jossek R., Bongaerts J., and Sprenger G.A. Characterization of a new feedback-resistant 3-deoxy-d-arabino-heptulosonate 7-phosphate synthase AroF of Escherichia coli. FEMS Microbiol. Lett. 202 (2001) 145-148
9. Krämer M., Bongaerts J., Bovenberg R., Kremer S., Muller U., Orf S., Wubbolts M., and Raeven L. Metabolic engineering for microbial production of shikimic. Acid. Metab. Eng. 5 (2003) 277-283
10. Li K., and Frost J.W. Microbial synthesis of 3-dehydroshikimic acid: a comparative analysis of d-xylose, l-arabinose, and d-glucose carbon sources. Biotechnol. Prog. 15 (1999) 876-883
11. Masai E., Momose K., Hara K., Nishikawa S., Katayama Y., and Fukuda M. Genetic and biochemical characterization of 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase and its role in the protocatechuate 4,5-cleavage pathway in Sphingomonas paucimobilis SYK-6. J. Bacteriol. 182 (2000) 6651-6658
12. Masai E., Katayama Y., and Fukuda M. Genetic and biochemical investigations on bacterial catabolic pathways for lignin-derived aromatic compounds. Biosci. Biotechnol. Biochem. 71 (2007) 1-15
13. + ion. Bull. Chem. Soc. Jpn. 80 (2007) 2436-2442
14. Michinobu T., Hishida M., Sato M., Katayama Y., Masai E., Nakamura M., Otsuka Y., Ohara S., and Shigehara K. Polyesters of 2-pyrone-4,6-dicarboxylic acid (PDC) obtained from a metabolic intermediate of lignin. Polym. J. 40 (2008) 68-75
15. Michinobu T., Inazawa Y., Hiraki K., Katayama Y., Masai E., Nakamura M., Ohara S., and Shigehara K. A novel biomass-based polymer prepared from lignin-derived stable metabolic intermediate by copper(I)-catalyzed azide-alkyne click reaction. Chem. Lett. 37 (2008) 154-155
16. Müller U., van Assema F., Gunsior M., Orf S., Kremer S., Schipper D., Wagemans A., Townsend C.A., Sonke T., Bovenberg R., and Wubbolts M. Metabolic engineering of the E. coli l-phenylalanine pathway for the production of d-phenylglycine d-Phg). Metab. Eng. 8 (2006) 196-208
17. Nelson N. A photometric adaptation of the Somogyi method for the determination of glucose. J. Biol. Chem. 153 (1944) 375-380
18. Noda Y., Nishikawa S., Shiozuka K., Kadokura H., Nakajima H., Yoda K., Katayama Y., Morohoshi N., Haraguchi T., and Yamasaki M. Molecular cloning of the protocatechuate 4,5-dioxygenase genes of Pseudomonas paucimobilis. J. Bacteriol. 172 (1990) 2704-2709
19. Otsuka Y., Nakamura M., Shigehara K., Sugimura K., Masai E., Ohara S., and Katayama Y. Efficient production of 2-pyrone 4,6-dicarboxylic acid as a novel polymer-based material from protocatechuate by microbial function. Appl. Microbiol. Biotechnol. 71 (2006) 608-614
20. Qi W.W., Vannelli T., Breinig S., Ben-Bassat A., Gatenby A.A., Haynie S.L., and Sariaslani F.S. Functional expression of prokaryotic and eukaryotic genes in Escherichia coli for conversion of glucose to p-hydroxystyrene. Metab. Eng. 9 (2007) 268-276
21. Shigehara K., Katayama Y., Nishikawa S., and Hotta Y. Polyester and process for producing the same. US Patent 6303745B1 (2001)
22. Shigehara K., Katayama Y., Nishikawa S., and Hotta Y. Polyamide and process for producing the same. US Patent 6340739B1 (2001)
23. Somogyi M. Notes on sugar determination. J. Biol. Chem. 195 (1952) 19-23
24. Sprenger G.A. From scratch to value: engineering Escherichia coli wild type cells to the production of l-phenylalanine and other fine chemicals derived from chorismate. Appl. Microbiol. Biotechnol. 75 (2007) 739-749
25. Vannelli T., Qi W.W., Sweigard J., Gatenby A.A., and Sariaslani F.S. Production of p-hydroxycinnamic acid from glucose in Saccharomyces cerevisiae and Escherichia coli by expression of heterologous genes from plants and fungi. Metab. Eng. 9 (2007) 142-151
26. Wallace B.J., and Pittard J. Genetic and biochemical analysis of the isoenzymes concerned in the first reaction of aromatic biosynthesis in Escherichia coli. J. Bacteriol. 93 (1967) 237-244
27. Werpy, T., Petersen, G., Aden, A., Bozell, J., Holladay, J., White, J., Manheim, A., 2004. Top value added chemicals from biomass, vol. I: Results of screening for potential candidates from sugars and synthesis gas. 〈http://www1.eere.energy.gov/biomass/pdfs/35523.pdf〉