Biosynthesis of adipic acid

Shengwu Gongcheng Xuebao/Chinese Journal of Biotechnology

Volumn 29, Issue 10, 2013, Pages 1374-1385

  Han, Li ^a   Chen, Wujiu ^a   Yuan, Fei ^a   Zhang, Yuanyuan ^a   Wang, Qinhong ^a   Ma, Yanhe ^a  

^a Tianjin Airport Economic Area   (China)

Author keywords

Adipic acid; Biosynthesis; Cis; Cis muconic acid; Metabolic engineering; Synthetic biology

Indexed keywords

ADIPIC ACID; ADIPIC ACID DERIVATIVE;

ARTICLE; BACTERIUM; FUNGUS; GENETICS; METABOLIC ENGINEERING; METABOLISM; METHODOLOGY; MICROBIOLOGY;

ADIPATES; BACTERIA; FUNGI; INDUSTRIAL MICROBIOLOGY; METABOLIC ENGINEERING; METABOLIC NETWORKS AND PATHWAYS;

EID: 84890852316     PISSN: 10003061     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (50)

1. Cavani F, Alini S. Synthesis of adipic acid: On the way to more sustainable production//Cavani F, Centi G, Perathoner S, et al. Sustainable Industrial Chemistry. Weinheim: Wiley VCH, 2009: 367-425.
2. Van de Vyver S, Román-Leshkov Y. Emerging catalytic processes for the production of adipic acid. Catal Sci Tech, 2013, 3 (6): 1465-1479.
3. Usui Y, Sato K. A green method of adipic acid synthesis: Organic solvent-and halide-free oxidation of cycloalkanones with 30% hydrogen peroxide. Green Chem, 2003, 5 (4): 373-375.
4. Damm M, Gutmann B, Kappe CO. Continuous-flow synthesis of adipic acid from cyclohexene using hydrogen peroxide in high-temperature explosive regimes. ChemSusChem, 2013, 6 (6): 978-982.
5. Polen T, Spelberg M, Bott M. Toward biotechnological production of adipic acid and precursors from biorenewables. J Biotechnol, 2013, 167 (2): 75-84.
6. Beardslee T, Picataggio S. Bio-based adipic acid from renewable oils. Lipid Technol, 2012, 24 (10): 223-225.
7. Van Duuren J, Brehmer B, Mars A, et al. A limited LCA of bio-adipic acid: Manufacturing the nylon-6, 6 precursor adipic acid using the benzoic acid degradation pathway from different feedstocks. Biotechnol Bioeng, 2011, 108 (6): 1298-1306.
8. Tsai SC, Tsai LD, Li YK. An isolated Candida albicans TL3 capable of degrading phenol at large concentration. Biosci Biotechnol Biochem, 2005, 69 (12): 2358-2367.
9. Nayak AS, Veeranagouda Y, Lee K, et al. Metabolism of acenaphthylene via 1, 2-dihydroxynaphthalene and catechol by Stenotrophomonas sp. RMSK. Biodegradation, 2009, 20 (6): 837-843.
10. Mucha K, Kwapisz E, Kucharska U, et al. Mechanism of aniline degradation by yeast strain Candida methanosorbosa BP-6. Pol J Microbiol, 2010, 59 (4): 311-315.
11. Ampe F, Uribelarrea JL, Aragao G, et al. Benzoate degradation via the ortho pathway in Alcaligenes eutrophus is perturbed by succinate. Appl Environ Microbiol, 1997, 63 (7): 2765-2770.
12. Mizuno S, Yoshikawa N, Seki M, et al. Microbial production of cis, cis-muconic acid from benzoic acid. Appl Microbiol Biotechnol, 1988, 28 (1): 20-25.
13. Bang SG, Choi CY. Do-stat fed-batch production of cis, cis-muconic acid from benzoic acid by Pseudomonas putida BM104. J Fermen Bioeng, 1995, 79 (4): 381-383.
14. Wu CM, Lee S, Lee Y, et al. Microbial synthesis of cis, cis-muconic acid by Sphingobaterium sp. GCG generated from effluent of a styrene monomer (SM) production plant. Enzyme Microb Technol, 2004, 35: 598-604.
15. Wu CM, Wu CC, Su CC, et al. Microbial synthesis of cis, cis-muconic acid from benzoate by Sphingobacterium sp. mutants. Biochem Eng J, 2006, 29 (1/2): 35-40.
16. Chatterjee S, Mallick S, Dutta TK. Pathways in the degradation of hydrolyzed alcohols of butyl benzyl phthalate in metabolically diverse Gordonia sp. strain MTCC 4818. J Mol Microbiol Biotechnol, 2005, 9 (2): 110-120.
17. van Duuren JB, Wijte D, Karge B, et al. pH-stat fed-batch process to enhance the production of cis, cis-muconate from benzoate by Pseudomonas putida KT2440-JD1. Biotechnol Prog, 2012, 28 (1): 85-92.
18. Nayak AS, Sanjeev Kumar S, Santosh Kumar M, et al. A catabolic pathway for the degradation of chrysene by Pseudoxanthomonas sp. PNK-04. FEMS Microbiol Lett, 2011, 320 (2): 128-134.
19. Nalli S, Cooper DG, Nicell JA. Interaction of metabolites with R. rhodochrous during the biodegradation of di-ester plasticizers. Chemosphere, 2006, 65 (9): 1510-1517.
20. Rosenberg S. Regulation of the mandelate pathway in Pseudomonas aeruginosa. J Bacteriol, 1971, 108 (3): 1257-1269.
21. Krivobok S, Benoit-Guyod JL, Seigle-Murandi F, et al. Diversity in phenol-metabolizing capability of 809 strains of Micromycetes. New Microbiol, 1994, 17 (1): 51-60.
22. Maxwell PC. Process for the production of muconic acid: US, 4731328. 1988-03-15.
23. Draths KM, Frost JW. Environmentally compatible synthesis of adipic acid from D-glucose. J Am Chem Soc, 1994, 116 (1): 399-400.
24. Niu W, Draths KM, Frost JW. Benzene-free synthesis of adipic acid. Biotechnol Prog, 2002, 18 (2): 201-211.
25. Wu YQ, Zhang YY, Tu R, et al. Construction of synthetic promoters for Escherichia coli and application in the biosynthesis of cis, cis-muconic acid. Chin J Biotech, 2013, 29 (6): 760-771 (in Chinese).
26. Sun X, Lin Y, Huang Q, et al. A novel muconic acid biosynthetic approach by shunting tryptophan biosynthesis via Anthranilate. Appl Environ Microbiol, 2013, 79 (13): 4024-4030.
27. Weber C, Bruckner C, Weinreb S, et al. Biosynthesis of cis, cis-muconic acid and its aromatic precursors, catechol and protocatechuic acid, from renewable feedstocks by Saccharomyces cerevisiae. Appl Environ Microbiol, 2012, 78 (23): 8421-8430.
28. Curran KA, Leavitt JM, Karim AS, et al. Metabolic engineering of muconic acid production in Saccharomyces cerevisiae. Metab Eng, 2013, 15: 55-66.
29. Fujiwara M, Golovleva LA, Saeki Y, et al. Extradiol cleavage of 3-substituted catechols by an intradiol dioxygenase, pyrocatechase, from a Pseudomonad. J Biol Chem, 1975, 250 (13): 4848-4855.
30. 18O studies of pyrogallol cleavage by catechol 1, 2-dioxygenase. J Biol Chem, 1984, 259 (21): 13056-13060.
31. Kou XF, Li Q. The preparation and properties of catechol-1, 2-dioxygenase from Pseudomonas putida. Acta Microbiol Sin, 1990, 30 (5): 397-399 (in Chinese).
32. Nakai C, Uyeyama H, Kagamiyama H, et al. Cloning, DNA sequencing, and amino acid sequencing of catechol 1, 2-dioxygenases (pyrocatechase) from Pseudomonas putida mt-2 and Pseudomonas arvilla C-1. Arch Biochem Biophys, 1995, 321 (2): 353-362.
33. Di Nardo G, Roggero C, Campolongo S, et al. Catalytic properties of catechol 1, 2-dioxygenase from Acinetobacter radioresistens S13 immobilized on nanosponges. Dalton Trans, 2009, (33): 6507-6512.
34. van Duuren JB, Wijte D, Leprince A, et al. Generation of a catR deficient mutant of P. putida KT2440 that produces cis, cis-muconate from benzoate at high rate and yield. J Biotechnol, 2011, 156 (3): 163-172.
35. Guzik U, Hupert-Kocurek K, Sitnik M, et al. High activity catechol 1, 2-dioxygenase from Stenotrophomonas maltophilia strain KB2 as a useful tool in cis, cis-muconic acid production. Antonie Van Leeuwenhoek, 2013, 103 (6): 1297-1307.
36. Earhart CA, Hall MD, Michaud-Soret I, et al. Crystallization of catechol-1, 2 dioxygenase from Pseudomonas arvilla C-1. J Mol Biol, 1994, 236 (1): 377-378.
37. Mampel J, Buescher JM, Meurer G, et al. Coping with complexity in metabolic engineering. Trends Biotechnol, 2013, 31 (1): 52-60.
38. Lee JW, Na D, Park JM, et al. Systems metabolic engineering of microorganisms for natural and non-natural chemicals. Nat Chem Biol, 2012, 8 (6): 536-546.
39. Cheng Q, Thomas SM, Kostichka K, et al. Genetic analysis of a gene cluster for cyclohexanol oxidation in Acinetobacter sp. strain SE19 by in vitro transposition. J Bacteriol, 2000, 182 (17): 4744-4751.
40. Brzostowicz PC, Gibson KL, Thomas SM, et al. Simultaneous identification of two cyclohexanone oxidation genes from a new Brevibacterium sp. using mRNA differential display. J Bacteriol, 2000, (182): 4241-4248.
41. Brzostowicz PC, Blasko MS, Rouvière PE. Identification of two gene clusters involved in cyclohexanone oxidation in Brevibacterium epidermidis strain HCU. Appl Microbiol Biotechnol, 2002, 58 (6): 781-789.
42. Dhamankar H, Prather KL. Microbial chemical factories: Recent advances in pathway engineering for synthesis of value added chemicals. Curr Opin Struct Biol, 2011, 21 (4): 488-494.
43. Djurdjevic I, Zelder O, Buckel W. Production of glutaconic acid in a recombinant Escherichia coli strain. Appl Environ Microbiol, 2011, 77 (1): 320-322.
44. Parthasarathy A, Pierik AJ, Kahnt J, et al. Substrate specificity of 2-hydroxyglutaryl-CoA dehydratase from Clostridium symbiosum: Toward a bio-based production of adipic acid. Biochemistry, 2011, (50): 3540-3550.
45. Dang L, White DW, Gross S, et al. Cancer-associated IDH1 mutations produce 2-hydroxyglutarate. Nature, 2009, 462 (7274): 739-744.
46. Dang L. A biocatalyst inspired by cancer. Nat Chem Biol, 2012, 8 (11): 874-875.
47. Reitman ZJ, Choi BD, Spasojevic I, et al. Enzyme redesign guided by cancer-derived IDH1 mutations. Nat Chem Biol, 2012, 8 (11): 887-889.
48. Wischgoll S, Demmer U, Warkentin E, et al. Structural basis for promoting and preventing decarboxylation in glutaryl-coenzyme a dehydrogenases. Biochemistry, 2010, 49 (25): 5350-5357.
49. Burgard A, Pharkya P, Osterhout R. Microorganisms for the production of adipic acid and other compounds: US, 7799545B2. 2009-03-27.
50. Thykaer J, Christensen B, Nielsen J. Metabolic network analysis of an adipoyl-7-ADCA-producing strain of Penicillium chrysogenum: Elucidation of adipate degradation. Metab Eng, 2002, 4 (2): 151-158.