Opportunities and challenges in biological lignin valorization

Current Opinion in Biotechnology

Volumn 42, Issue , 2016, Pages 40-53

  Beckham, Gregg T ^a   Johnson, Christopher W ^a   Karp, Eric M ^a   Salvachúa, Davinia ^a   Vardon, Derek R ^a  

^a NATIONAL RENEWABLE ENERGY LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; BACTERIA; ENZYMES; FEEDSTOCKS; METABOLIC ENGINEERING; METABOLISM; REFINING;

BIOLOGICAL SOLUTIONS; CENTRAL CARBON METABOLISMS; LIGNIN DEPOLYMERIZATION; LIGNINOLYTIC ENZYMES; LIGNOCELLULOSIC BIOMASS; RESEARCH OPPORTUNITIES; SUBSTRATE SPECIFICITY; TECHNICAL CHALLENGES;

LIGNIN;

2 PYRONE 4,6 DICARBOXYLIC ACID; 4 HYDROXYBENZOATE 3 MONOOXYGENASE; 4 HYDROXYBENZOIC ACID; ABC TRANSPORTER; CARBON; CAROTENOID; CYTOCHROME P450; DICARBOXYLIC ACID; FATTY ACID; FERULIC ACID; HYDROLASE; LIGNIN; MUCONIC ACID; PARA COUMARIC ACID; POLYHYDROXYALKANOIC ACID; POLYSACCHARIDE; TRIACYLGLYCEROL; UNCLASSIFIED DRUG; VANILLATE DEMETHYLASE; VANILLIC ACID;

ACINETOBACTER BAYLYI; AMYCOLATOPSIS; AZOARCUS; BACILLUS SUBTILIS; BIOSYNTHESIS; BIOTECHNOLOGY; CARBON METABOLISM; CATABOLISM; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; ENZYME SPECIFICITY; ESCHERICHIA COLI; FRACTIONATION; HOST SELECTION; HYDROLYSIS; LIGNIN VALORIZATION; METABOLIC ENGINEERING; MICROBIOLOGY; MICROORGANISM; MOLECULAR WEIGHT; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PSEUDOMONAS FLUORESCENS; PSEUDOMONAS PUTIDA; REDUCTIVE CATALYTIC FRACTIONATION; REVIEW; RHODOCOCCUS JOSTII; RHODOCOCCUS OPACUS; RHODOPSEUDOMONAS PALUSTRIS; SOLUBILIZATION; SPHINGOMONAS; THAUERA AROMATICA; BACTERIUM; BIOMASS; METABOLISM; PROCEDURES;

BIOMASS; ENZYMES; LIGNINS; LIGNOCELLULOSE; MICROORGANISMS;

BACTERIA; BIOMASS; BIOTECHNOLOGY; LIGNIN; METABOLIC ENGINEERING; SUBSTRATE SPECIFICITY;

EID: 84960390972     PISSN: 09581669     EISSN: 18790429     Source Type: Journal    
DOI: 10.1016/j.copbio.2016.02.030     Document Type: Review

References (124)

1. Ralph J. Hydroxycinnamates in lignification. Phytochem Rev 2010, 9:65-83.
2. Chen F., Tobimatsu Y., Havkin-Frenkel D., Dixon R.A., Ralph J. A polymer of caffeyl alcohol in plant seeds. Proc Natl Acad Sci 2012, 109:1772-1777.
3. Bonawitz N.D., Im Kim J., Tobimatsu Y., Ciesielski P.N., Anderson N.A., Ximenes E., Maeda J., Ralph J., Donohoe B.S., Ladisch M. Disruption of Mediator rescues the stunted growth of a lignin-deficient Arabidopsis mutant. Nature 2014, 509:376-380.
4. Wagner A., Tobimatsu Y., Phillips L., Flint H., Geddes B., Lu F., Ralph J. Syringyl lignin production in conifers: proof of concept in a Pine tracheary element system. Proc Natl Acad Sci 2015, 112:6218-6223.
5. Wilkerson C., Mansfield S., Lu F., Withers S., Park J.-Y., Karlen S., Gonzales-Vigil E., Padmakshan D., Unda F., Rencoret J., et al. Monolignol ferulate transferase introduces chemically labile linkages into the lignin backbone. Science 2014, 344:90-93.
6. Eudes A., Sathitsuksanoh N., Baidoo E.E., George A., Liang Y., Yang F., Singh S., Keasling J.D., Simmons B.A., Loqué D. Expression of a bacterial 3-dehydroshikimate dehydratase reduces lignin content and improves biomass saccharification efficiency. Plant Biotechnol J 2014.
7. Davis R., Tao L., Tan E., Biddy M.J., Beckham G.T., Scarlata C., Jacobson J., Cafferty K., Ross J., Lukas J., et al. Process Design and Economics for the Conversion of Lignocellulosic Biomass to Hydrocarbons: Dilute-Acid Prehydrolysis and Enzymatic Hydrolysis Deconstruction of Biomass to Sugars and Biological Conversion of Sugars to Hydrocarbons 2013, NREL, Golden, CO. Laboratory NRE (Ed.).
8. Ragauskas A.J., Beckham G.T., Biddy M.J., Chandra R., Chen F., Davis M.F., Davison B.H., Dixon R.A., Gilna P., Keller M., et al. Lignin valorization: improving lignin processing in the biorefinery. Science 2014, 344:1246843.
9. Zakzeski J., Bruijnincx P.C.A., Jongerius A.L., Weckhuysen B.M. The catalytic valorization of lignin for the production of renewable chemicals. Chem Rev 2010, 110:3552-3599.
10. Martínez Á.T., Speranza M., Ruiz-Dueñas F.J., Ferreira P., Camarero S., Guillén F., Martínez M.J., Gutiérrez A., del Río J.C. Biodegradation of lignocellulosics: microbial, chemical, and enzymatic aspects of the fungal attack of lignin. Int Microbiol 2010, 8:195-204.
11. Fuchs G., Boll M., Heider J. Microbial degradation of aromatic compounds - from one strategy to four. Nat Rev Microbiol 2011, 9:803-816.
12. Boll M., Löffler C., Morris B.E., Kung J.W. Anaerobic degradation of homocyclic aromatic compounds via arylcarboxyl-coenzyme A esters: organisms, strategies and key enzymes. Environ Microbiol 2014, 16:612-627.
13. Bugg T.D.H., Rahmanpour R. Enzymatic conversion of lignin into renewable chemicals. Curr Opin Chem Biol 2015, 29:10-17.
14. Chundawat S.P.S., Beckham G.T., Himmel M.E., Dale B.E. Deconstruction of lignocellulosic biomass to fuels and chemicals. Ann Rev Chem Biomol Eng 2011, 2:121-145.
15. George A., Brandt A., Tran K., Zahari S.M.N.S., Klein-Marcuschamer D., Sun N., Sathitsuksanoh N., Shi J., Stavila V., Parthasarathi R., Singh S. Design of low-cost ionic liquids for lignocellulosic biomass pretreatment. Green Chem 2015, 17:1728-1734.
16. Socha A.M., Parthasarathi R., Shi J., Pattathil S., Whyte D., Bergeron M., George A., Tran K., Stavila V., Venkatachalam S., Hahn M.G., Simmons B.A., Singh S. Efficient biomass pretreatment using ionic liquids derived from lignin and hemicellulose. Proc Natl Acad Sci 2014, 111:E3587-E3595.
17. Song Q., Wang F., Cai J., Wang Y., Zhang J., Yu W., Xu J. Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation-hydrogenolysis process. Energy Environ Sci 2013, 6:994-1007.
18. Ferrini P., Rinaldi R. Catalytic biorefining of plant biomass to non-pyrolytic lignin bio-oil and carbohydrates through hydrogen transfer reactions. Angew Chem Int Ed 2014, 53:8634-8639.
19. Van den Bosch S., Schutyser W., Vanholme R., Driessen T., Koelewijn S.-F., Renders T., De Meester B., Huijgen W., Dehaen W., Courtin C. Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps. Energy Environ Sci 2015.
20. Parsell T., Yohe S., Degenstein J., Jarrell T., Klein I., Gencer E., Hewetson B., Hurt M., Im Kim J., Choudhari H. A synergistic biorefinery based on catalytic conversion of lignin prior to cellulose starting from lignocellulosic biomass. Green Chem 2015, 17:1492-1499.
21. Luo H., Klein I.M., Jiang Y., Zhu H., Liu B., Kenttamaa H.I., Abu-Omar M.M. Total utilization of miscanthus biomass, lignin and carbohydrates, using earth abundant nickel catalyst. ACS Sustain Chem Eng 2016.
22. Chen X.W., Tao L., Shekiro J., Mohaghaghi A., Decker S., Wang W., Smith H., Park S., Himmel M.E., Tucker M. Improved ethanol yield and reduced minimum ethanol selling price (MESP) by modifying low severity dilute acid pretreatment with deacetylation and mechanical refining: (1) Experimental. Biotechnol Biofuels 2012, 5.
23. Karp E.M., Donohoe B.S., O'Brien M.H., Ciesielski P.N., Mittal A., Biddy M.J., Beckham G.T. Alkaline pretreatment of corn stover: bench-scale fractionation and stream characterization. ACS Sustain Chem Eng 2014, 2:1481-1491.
24. Karp E.M., Resch M.G., Donohoe B.S., Ciesielski P.N., O'Brien M.H., Nill J.E., Mittal A., Biddy M.J., Beckham G.T. Alkaline pretreatment of switchgrass. ACS Sustain Chem Eng 2015, 3:1479-1491.
25. Linger J.G., Vardon D.R., Guarnieri M.G., Karp E.M., Hunsinger G.B., Franden M.A., Johnson C.W., Chupka G., Strathmann T.J., Pienkos P.T., et al. Lignin valorization through integrated biological funneling and chemical catalysis. Proc Natl Acad Sci 2014, 111:12013-12018.
26. Li C., Zhao X., Wang A., Huber G.W., Zhang T. Catalytic transformation of lignin for the production of chemicals and fuels. Chem Rev 2015, 115:11559-11624.
27. Ma R., Xu Y., Zhang X. Catalytic oxidation of biorefinery lignin to value-added chemicals to support sustainable biofuel production. ChemSusChem 2015, 8:24-51.
28. Vardon D.R., Franden M.A., Johnson C.W., Karp E.M., Guarnieri M.T., Linger J.G., Salm M.J., Strathmann T.J., Beckham G.T. Adipic acid production from lignin. Energy Environ Sci 2015, 8:617-628.
29. Johnson C.W., Beckham G.T. Aromatic catabolic pathway selection for optimal production of pyruvate and lactate from lignin. Metab Eng 2015, 28:240-247.
30. Salvachúa D., Karp E.M., Nimlos C.T., Vardon D.R., Beckham G.T. Towards lignin consolidated bioprocessing: simultaneous lignin depolymerization and product generation by bacteria. Green Chem 2015, 17:4951-4967.
31. McLeod M.P., Warren R.L., Hsiao W.W.L., Araki N., Myhre M., Fernandes C., Miyazawa D., Wong W., Lillquist A.L., Wang D., et al. The complete genome of Rhodococcus sp. RHA1 provides insights into a catabolic powerhouse. Proc Natl Acad Sci 2006, 103:15582-15587.
32. Kosa M., Ragauskas A.J. Lignin to lipid bioconversion by oleaginous Rhodococci. Green Chem 2013, 15:2070-2074.
33. Barbe V., Vallenet D., Fonknechten N., Kreimeyer A., Oztas S., Labarre L., Cruveiller S., Robert C., Duprat S., Wincker P., et al. Unique features revealed by the genome sequence of Acinetobacter sp. ADP1, a versatile and naturally transformation competent bacterium. Nucleic Acids Res 2004, 32:5766-5779.
34. Masai E., Katayama Y., Fukuda M. Genetic and biochemical investigations on bacterial catabolic pathways for lignin-derived aromatic compounds. Biosci Biotechnol Biochem 2007, 71:1-15.
35. Masai E., Katayama Y., Nishikawa S., Fukuda M. Characterization of Sphingomonas paucimobilis SYK-6 genes involved in degradation of lignin-related compounds. J Ind Microbiol Biotechnol 1999, 23:364-373.
36. Masai E., Kamimura N., Kasai D., Oguchi A., Ankai A., Fukui S., Takahashi M., Yashiro I., Sasaki H., Harada T. Complete genome sequence of Sphingobium sp. strain SYK-6, a degrader of lignin-derived biaryls and monoaryls. J Bacteriol 2012, 194:534-535.
37. Camarero S., Martínez M., Martínez A. Lignin-degrading enzymes produced by Pleurotus species during solid state fermentation of wheat straw. Advances in Solid State Fermentation 1997, 335-345. Springer (Ed.).
38. Camarero S., Martínez M.J., Martínez A.T. Understanding lignin biodegradation for the improved utilization of plant biomass in modern biorefineries. Biofuels Bioprod Biorefin 2014, 8:615-625.
39. Nikel P.I., Martínez-García E., de Lorenzo V. Biotechnological domestication of pseudomonads using synthetic biology. Nat Rev Microbiol 2014, 12:368-379.
40. Martínez-García E., Nikel P.I., Aparicio T., de Lorenzo V. Pseudomonas 2.0: genetic upgrading of P. putida KT2440 as an enhanced host for heterologous gene expression. Microb Cell Fact 2014, 13:159.
41. Lieder S., Nikel P.I., de Lorenzo V., Takors R. Genome reduction boosts heterologous gene expression in Pseudomonas putida. Microb Cell Fact 2015, 14:23.
42. Fernández H., Prandoni N., Fernández-Pascual M., Fajardo S., Morcillo C., Díaz E., Carmona M. Azoarcus sp. CIB, an anaerobic biodegrader of aromatic compounds shows an endophytic lifestyle. PLOS ONE 2014, 9:e110771.
43. Heider J., Boll M., Breese K., Breinig S., Ebenau-Jehle C., Feil U., Gad'on N., Laempe D., Leuthner B., Mohamed M.E.-S. Differential induction of enzymes involved in anaerobic metabolism of aromatic compounds in the denitrifying bacterium Thauera aromatica. Arch Microbiol 1998, 170:120-131.
44. Trautwein K., Grundmann O., Wöhlbrand L., Eberlein C., Boll M., Rabus R. Benzoate mediates repression of C4-dicarboxylate utilization in "Aromatoleum aromaticum" EbN1. J Bacteriol 2012, 194:518-528.
45. Billings A.F., Fortney J.L., Hazen T.C., Simmons B., Davenport K.W., Goodwin L., Ivanova N., Kyrpides N.C., Mavromatis K., Woyke T. Genome sequence and description of the anaerobic lignin-degrading bacterium Tolumonas lignolytica sp. nov. Stand Genomic Sci 2015, 10.
46. Woo H.L., Ballor N.R., Hazen T.C., Fortney J.L., Simmons B., Davenport K.W., Goodwin L., Ivanova N., Kyrpides N.C., Mavromatis K. Complete genome sequence of the lignin-degrading bacterium Klebsiella sp. strain BRL6-2. Stand Genomic Sci 2014, 9:19.
47. DeAngelis K.M., Sharma D., Varney R., Simmons B., Isern N.G., Markilllie L.M., Nicora C., Norbeck A.D., Taylor R.C., Aldrich J.T. Evidence supporting dissimilatory and assimilatory lignin degradation in Enterobacter lignolyticus SCF1. Front Microbiol 2013, 4.
48. Bugg T.D., Ahmad M., Hardiman E.M., Singh R. The emerging role for bacteria in lignin degradation and bio-product formation. Curr Opin Biotechnol 2011, 22:394-400.
49. Bugg T.D., Ahmad M., Hardiman E.M., Rahmanpour R. Pathways for degradation of lignin in bacteria and fungi. Nat Prod Rep 2011, 28:1883-1896.
50. Roberts J.N., Singh R., Grigg J.C., Murphy M.E., Bugg T.D., Eltis L.D. Characterization of dye-decolorizing peroxidases from Rhodococcus jostii RHA1. Biochemistry 2011, 50:5108-5119.
51. Ahmad M., Roberts J.N., Hardiman E.M., Singh R., Eltis L.D., Bugg T.D.H. Identification of DypB from Rhodococcus jostii RHA1 as a lignin peroxidase. Biochemistry 2011, 50:5096-5107.
52. Santos A., Mendes S., Brissos V., Martins L.O. New dye-decolorizing peroxidases from Bacillus subtilis and Pseudomonas putida MET94: towards biotechnological applications. Appl Microbiol Biotechnol 2014, 98:2053-2065.
53. Brown M.E., Barros T., Chang M.C. Identification and characterization of a multifunctional dye peroxidase from a lignin-reactive bacterium. ACS Chem Biol 2012, 7:2074-2081.
54. Hullo M.-F., Moszer I., Danchin A., Martin-Verstraete I. CotA of Bacillus subtilis is a copper-dependent laccase. J Bacteriol 2001, 183:5426-5430.
55. Picart P., de María P.D., Schallmey A. From gene to biorefinery: microbial β-etherases as promising biocatalysts for lignin valorization. Front Microbiol 2015, 6.
56. Strachan C.R., Singh R., VanInsberghe D., Ievdokymenko K., Budwill K., Mohn W.W., Eltis L.D., Hallam S.J. Metagenomic scaffolds enable combinatorial lignin transformation. Proc Natl Acad Sci 2014, 111:10143-10148.
57. Armstrong Z., Mewis K., Strachan C., Hallam S.J. Biocatalysts for biomass deconstruction from environmental genomics. Curr Opin Chem Biol 2015, 29:18-25.
58. Chung D., Cha M., Guss A.M., Westpheling J. Direct conversion of plant biomass to ethanol by engineered Caldicellulosiruptor bescii. Proc Natl Acad Sci 2014, 201402210.
59. Lynd L.R., Van Zyl W.H., McBRIDE J.E., Laser M. Consolidated bioprocessing of cellulosic biomass: an update. Curr Opin Biotechnol 2005, 16:577-583.
60. Zhao C., Xie S., Pu Y., Zhang R., Huang F., Ragauskas A.J., Yuan J.S. Synergistic enzymatic and microbial lignin conversion. Green Chem 2015.
61. Payne C.M., Knott B.C., Mayes H.B., Hansson H., Himmel M.E., Sandgren M., Ståhlberg J., Beckham G.T. Fungal cellulases. Chem Rev 2015, 115:1308-1448.
62. Salvachúa D., Prieto A., Mattinen M.-L., Tamminen T., Liitiä T., Lille M., Willför S., Martínez A.T., Martínez M.J., Faulds C.B. Versatile peroxidase as a valuable tool for generating new biomolecules by homogeneous and heterogeneous cross-linking. Enzyme Microb Technol 2013, 52:303-311.
63. Harwood C.S., Nichols N.N., Kim M.-K., Ditty J.L., Parales R.E. Identification of the pcaRKF gene cluster from Pseudomonas putida: involvement in chemotaxis, biodegradation, and transport of 4-hydroxybenzoate. J Bacteriol 1994, 176:6479-6488.
64. Nichols N.N., Harwood C.S. PcaK, a high-affinity permease for the aromatic compounds 4-hydroxybenzoate and protocatechuate from Pseudomonas putida. J Bacteriol 1997, 179:5056-5061.
65. Xu Y., Wang S.-H., Chao H.-J., Liu S.-J., Zhou N.-Y. Biochemical and molecular characterization of the gentisate transporter GenK in Corynebacterium glutamicum. PLoS ONE 2012, 7:e38701.
66. Michalska K., Chang C., Mack J.C., Zerbs S., Joachimiak A., Collart F.R. Characterization of transport proteins for aromatic compounds derived from lignin: benzoate derivative binding proteins. J Mol Biol 2012, 423:555-575.
67. Otani H., Lee Y.-E., Casabon I., Eltis L.D. Characterization of p-hydroxycinnamate catabolism in a soil Actinobacterium. J Bacteriol 2014, 196:4293-4303.
68. Jiménez J.I., Miñambres B., Garcia J.L., Díaz E. Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440. Environ Microbiol 2002, 4:824-841.
69. Nordlund I., Powlowski J., Shingler V. Complete nucleotide sequence and polypeptide analysis of multicomponent phenol hydroxylase from Pseudomonas sp. strain CF600. J Bacteriol 1990, 172:6826-6833.
70. Nurk A., Kasak L., Kivisaar M. Sequence of the gene (pheA) encoding phenol monooxygenase from Pseudomonas sp. EST1001: expression in Escherichia coli and Pseudomonas putida. Gene 1991, 102:13-18.
71. Saa L., Jaureguibeitia A., Largo E., Llama M.J., Serra J.L. Cloning, purification and characterization of two components of phenol hydroxylase from Rhodococcus erythropolis UPV-1. Appl Microbiol Biotechnol 2010, 86:201-211.
72. Dardas A., Gal D., Barrelle M., Sauret-Ignazi G., Sterjiades R., Pelmont J. The demethylation of guaiacol by a new bacterial cytochrome P-450. Arch Biochem Biophys 1985, 236:585-592.
73. Eltis L.D., Karlson U., Timmis K.N. Purification and characterization of cytochrome P450RR1 from Rhodococcus rhodochrous. Eur J Biochem 1993, 213:211-216.
74. Kawahara N., Ikatsu H., Kawata H., Miyoshi S.-i., Tomochika K.-i., Sinoda S. Purification and characterization of 2-ethoxyphenol-induced cytochrome P450 from Corynebacterium sp. strain EP1. Can J Microbiol 1999, 45:833-839.
75. Camarero S., Ibarra D., Martínez M.J., Martínez Á.T. Lignin-derived compounds as efficient laccase mediators for decolorization of different types of recalcitrant dyes. Appl Environ Microbiol 2005, 71:1775-1784.
76. Sainsbury P.D., Hardiman E.M., Ahmad M., Otani H., Seghezzi N., Eltis L.D., Bugg T.D.H. Breaking down lignin to high-value chemicals: the conversion of lignocellulose to vanillin in a gene deletion mutant of Rhodococcus jostii RHA1. ACS Chem Biol 2013, 8:2151-2156.
77. Thompson B., Machas M., Nielsen D.R. Creating pathways towards aromatic building blocks and fine chemicals. Curr Opin Biotechnol 2015, 36:1-7.
78. Vaillancourt F.H., Bolin J.T., Eltis L.D. The ins and outs of ring-cleaving dioxygenases. Crit Rev Biochem Mol Biol 2006, 41:241-267.
79. Bugg T.D. Dioxygenase enzymes: catalytic mechanisms and chemical models. Tetrahedron 2003, 59:7075-7101.
80. Schlosrich J., Eley K.L., Crowley P.J., Bugg T.D. Directed evolution of a non-heme-iron-dependent extradiol catechol dioxygenase: identification of mutants with intradiol oxidative cleavage activity. ChemBioChem 2006, 7:1899-1908.
81. Barry K.P., Cohn E.F., Ngu A., Taylor E.A. Improving alternate lignin catabolite utilization of LigAB from Sphingobium sp. strain SYK-6 through site directed mutagenesis. Process Biochem 2015, 50:1634-1639.
82. Barry K.P., Taylor E.A. Characterizing the promiscuity of LigAB, a lignin catabolite degrading extradiol dioxygenase from Sphingomonas paucimobilis SYK-6. Biochemistry 2013, 52:6724-6736.
83. Han L., Liu P., Sun J., Wu Y., Zhang Y., Chen W., Lin J., Wang Q., Ma Y. Engineering catechol 1,2-dioxygenase by design for improving the performance of the cis,cis-muconic acid synthetic pathway in Escherichia coli. Sci Rep 2015, 5.
84. Matera I., Ferraroni M., Kolomytseva M., Golovleva L., Scozzafava A., Briganti F. Catechol 1,2-dioxygenase from the Gram-positive Rhodococcus opacus 1CP: quantitative structure/activity relationship and the crystal structures of native enzyme and catechols adducts. J Struct Biol 2010, 170:548-564.
85. Barry K.P., Ngu A., Cohn E.F., Cote J.M., Burroughs A.M., Gerbino J.P., Taylor E.A. Exploring allosteric activation of LigAB from Sphingobium sp. strain SYK-6 through kinetics, mutagenesis and computational studies. Arch Biochem Biophys 2015, 567:35-45.
86. Sugimoto K., Senda M., Kasai D., Fukuda M., Masai E., Senda T. Molecular mechanism of strict substrate specificity of an extradiol dioxygenase, DesB, derived from Sphingobium sp. SYK-6. PLoS ONE 2014, 9:e92249.
87. Draths K.M., Frost J.W. Environmentally compatible synthesis of adipic acid from d-glucose. J Am Chem Soc 1994, 116:399-400.
88. Polen T., Spelberg M., Bott M. Toward biotechnological production of adipic acid and precursors from biorenewables. J Biotechnol 2013, 167:75-84.
89. Curran K.A., Leavitt J.M., Karim A.S., Alper H.S. Metabolic engineering of muconic acid production in Saccharomyces cerevisiae. Metab Eng 2013, 15:55-66.
90. Sonoki T., Morooka M., Sakamoto K., Otsuka Y., Nakamura M., Jellison J., Goodell B. Enhancement of protocatechuate decarboxylase activity for the effective production of muconate from lignin-related aromatic compounds. J Biotechnol 2014, 192:71-77.
91. Weber C., Brückner C., Weinreb S., Lehr C., Essl C., Boles E. Biosynthesis of cis,cis-muconic acid and its aromatic precursors, catechol and protocatechuic acid, from renewable feedstocks by Saccharomyces cerevisiae. Appl Environ Microbiol 2012, 78:8421-8430.
92. Michinobu T., Hishida M., Sato M., Katayama Y., Masai E., Nakamura M., Otsuka Y., Ohara S., Shigehara K. Polyesters of 2-pyrone-4,6-dicarboxylic acid (PDC) obtained from a metabolic intermediate of lignin. Polym J 2008, 40:68-75.
93. Hishida M., Shikinaka K., Katayama Y., Kajita S., Masai E., Nakamura M., Otsuka Y., Ohara S., Shigehara K. Polyesters of 2-pyrone-4,6-dicarboxylic acid (PDC) as bio-based plastics exhibiting strong adhering properties. Polym J 2009, 41:297-302.
94. Mycroft Z., Gomis M., Mines P., Law P., Bugg T.D. Biocatalytic conversion of lignin to aromatic dicarboxylic acids in Rhodococcus jostii RHA1 by re-routing aromatic degradation pathways. Green Chem 2015, 17:4974-4979.
95. Okamura-Abe Y., Abe T., Nishimura K., Kawata Y., Sato-Izawa K., Otsuka Y., Nakamura M., Kajita S., Masai E., Sonoki T. Beta-ketoadipic acid and muconolactone production from a lignin-related aromatic compound through the protocatechuate 3,4-metabolic pathway. J Biosci Bioeng 2015.
96. Asano Y., Yamamoto Y., Yamada H. Catechol 2,3-dioxygenase-catalyzed synthesis of picolinic acids from catechols. Biosci Biotechnol Biochem 1994, 58:2054-2056.
97. Gosling A., Fowler S.J., O'Shea M.S., Straffon M., Dumsday G., Zachariou M. Metabolic production of a novel polymer feedstock, 3-carboxy muconate, from vanillin. Appl Microbiol Biotechnol 2011, 90:107-116.
98. Peralta-Yahya P.P., Zhang F.Z., del Cardayre S.B., Keasling J.D. Microbial engineering for the production of advanced biofuels. Nature 2012, 488:320-328.
99. van Duuren J.B., Wijte D., Karge B., Martins dos Santos V.A., Yang Y., Mars A.E., Eggink G. pH-stat fed-batch process to enhance the production of cis,cis-muconate from benzoate by Pseudomonas putida KT2440-JD1. Biotechnol Prog 2012, 28:85-92.
100. del Castillo T., Ramos J.L. Simultaneous catabolite repression between glucose and toluene metabolism in Pseudomonas putida is channeled through different signaling pathways. J Bacteriol 2007, 189:6602-6610.
101. Xie N.-Z., Liang H., Huang R.-B., Xu P. Biotechnological production of muconic acid: current status and future prospects. Biotechnol Adv 2014, 32:615-622.
102. Bang S.-G., Choi C.Y. DO-stat fed-batch production of cis,cis-muconic acid from benzoic acid by Pseudomonas putida BM014. J Ferment Bioeng 1995, 79:381-383.
103. Madkour M.H., Heinrich D., Alghamdi M.A., Shabbaj I.I., Steinbüchel A. PHA recovery from biomass. Biomacromolecules 2013, 14:2963-2972.
104. Ramaswamy S., Huang H.-J., Ramarao B.V. Separation and Purification Technologies in Biorefineries 2013, John Wiley & Sons.
105. Heeres A.S., Picone C.S., van der Wielen L.A., Cunha R.L., Cuellar M.C. Microbial advanced biofuels production: overcoming emulsification challenges for large-scale operation. Trends Biotechnol 2014, 32:221-229.
106. Lu R., Lu F., Chen J., Yu W., Huang Q., Zhang J., Xu J. Production of diethyl terephthalate from biomass-derived muconic acid. Angew Chem 2015.
107. Gallezot P. Conversion of biomass to selected chemical products. Chem Soc Rev 2012, 41:1538-1558.
108. Sheldon R.A. Green and sustainable manufacture of chemicals from biomass: state of the art. Green Chem 2014, 16:950-963.
109. Wettstein S.G., Alonso D.M., Gürbüz E.I., Dumesic J.A. A roadmap for conversion of lignocellulosic biomass to chemicals and fuels. Curr Opin Chem Eng 2012, 1:218-224.
110. Schwartz T.J., O'Neill B.J., Shanks B.H., Dumesic J.A. Bridging the chemical and biological catalysis gap: challenges and outlooks for producing sustainable chemicals. ACS Catal 2014, 4:2060-2069.
111. Kumar P., Barrett D.M., Delwiche M.J., Stroeve P. Methods for pretreatment of lignocellulosic biomass for efficient hydrolysis and biofuel production. Ind Eng Chem Res 2009, 48:3713-3729.
112. Menon V., Rao M. Trends in bioconversion of lignocellulose: biofuels, platform chemicals & biorefinery concept. Prog Energy Combust Sci 2012, 38:522-550.
113. Baucher M., Halpin C., Petit-Conil M., Boerjan W. Lignin: genetic engineering and impact on pulping. Crit Rev Biochem Mol Biol 2003, 38:305-350.
114. Vanholme R., Morreel K., Ralph J., Boerjan W. Lignin engineering. Curr Opin Plant Biol 2008, 11:278-285.
115. Chen F., Dixon R.A. Lignin modification improves fermentable sugar yields for biofuel production. Nat Biotechnol 2007, 25:759-761.
116. Weng J.-K., Li X., Bonawitz N.D., Chapple C. Emerging strategies of lignin engineering and degradation for cellulosic biofuel production. Curr Opin Biotechnol 2008, 19:166-172.
117. Chen F., Tobimatsu Y., Jackson L., Nakashima J., Ralph J., Dixon R.A. Novel seed coat lignins in the Cactaceae: structure, distribution and implications for the evolution of lignin diversity. Plant J 2013, 73:201-211.
118. Heitner C., Dimmel D., Schmidt J. Lignin and Lignans: Advances in Chemistry 2010, CRC Press.
119. Lupoi J.S., Singh S., Parthasarathi R., Simmons B.A., Henry R.J. Recent innovations in analytical methods for the qualitative and quantitative assessment of lignin. Renew Sustain Energy Rev 2015, 49:871-906.
120. Niemelä K., Sjöström E. Simultaneous identification of aromatic and aliphatic low molecular weight compounds from alkaline pulping liquor by capillary gas-liquid chromatography-mass spectrometry. Holzforschung 1986, 40:361-368.
121. Kuban P., Karlberg B. On-line monitoring of kraft pulping liquors with a valveless flow injection-capillary electrophoresis system. Anal Chim Acta 2000, 404:19-28.
122. Volgger D., Zemann A., Bonn G. Determination of phenols, inorganic anions, and carboxylic acids in Kraft black liquors by capillary electrophoresis. J High Resolut Chromatogr 1998, 21:3-10.
123. Shackman J.G., Munson M.S., Ross D. Gradient elution moving boundary electrophoresis for high-throughput multiplexed microfluidic devices. Anal Chem 2007, 79:565-571.
124. Strychalski E.A., Henry A.C., Ross D. Microfluidic analysis of complex samples with minimal sample preparation using gradient elution moving boundary electrophoresis. Anal Chem 2009, 81:10201-10207.