Two-Dimensional NMR Evidence for Cleavage of Lignin and Xylan Substituents in Wheat Straw Through Hydrothermal Pretreatment and Enzymatic Hydrolysis

Bioenergy Research

Volumn 6, Issue 1, 2013, Pages 211-221

  Yelle, Daniel J ^a   Kaparaju, Prasad ^b,d   Hunt, Christopher G ^a   Hirth, Kolby ^a   Kim, Hoon ^c   Ralph, John ^c   Felby, Claus ^b  

^a FOREST PRODUCTS LABORATORY   (United States)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

^d UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

Cinnamates; Hydrothermal; Lignin; O acetyls; Polysaccharides; Uronic acids; Wheat straw; aryl ethers

Indexed keywords

ACETYLATION; AROMATIC COMPOUNDS; BIOETHANOL; CARBOXYLIC ACIDS; CELLULOSE; CHEMICAL ANALYSIS; ETHERS; HYDROCHEMISTRY; LIGNIN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYSACCHARIDES; QUANTUM THEORY; STRAW;

ARYL ETHER; CINNAMATES; HYDROTHERMAL; URONIC ACIDS; WHEAT STRAWS;

ENZYMATIC HYDROLYSIS;

TRITICUM AESTIVUM;

EID: 84873721537     PISSN: 19391234     EISSN: 19391242     Source Type: Journal    
DOI: 10.1007/s12155-012-9247-6     Document Type: Article

References (70)

1. Larsen J, Petersen MØ, Thirup L, Li HW, Iversen FK (2008) The IBUS process - lignocellulosic bioethanol close to a commercial reality. Chem Eng Technol 31(5): 765-772.
2. Aspinall GO (1982) Isolation and fractionation of polysaccharides. In: Aspinall GO (ed) The Polysaccharides, vol 1. Academic, New York, pp 19-35.
3. Lai YZ, Sarkanen KV (1971) Isolation and structural studies. In: Sarkanen KV, Ludwig CH (eds) Lignins. Occurrence, formation, structure and reactions. Wiley Interscience, New York, pp 165-240.
4. Lu F, Ralph J (2003) Non-degradative dissolution and acetylation of ball-milled plant cell walls: high-resolution solution-state NMR. Plant J 35(4): 535-544.
5. Forziati FH, Stone WK, Rowen JW, Appel WD (1950) Cotton powder for infrared transmission measurements. J Res Nat Bur Stand 45(2): 109-113.
6. Schwanninger M, Rodrigues JC, Periera H, Hinterstoisser B (2004) Effects of short-time vibratory ball milling on the shape of FT-IR spectra of wood and cellulose. Vib Spectrosc 36: 23-40.
7. Fujimoto A, Matsumoto Y, Chang HM, Meshitsuka G (2005) Quantitative evaluation of milling effects on lignin structure during the isolation process of milled wood lignin. J Wood Sci 51: 89-91.
8. Ikeda T, Holtman K, Kadla JF, Chang HM, Jameel H (2002) Studies on the effect of ball milling on lignin structure using a modified DFRC method. J Agric Food Chem 50(1): 129-135.
9. Yelle DJ, Ralph J, Frihart CR (2008) Characterization of nonderivatized plant cell walls using high-resolution solution-state NMR spectroscopy. Magn Reson Chem 46: 508-517.
10. 6. Bioenerg Res 1: 56-66.
11. Lapierre C (2011) Personal Communication.
12. Lapierre C, Pollet B, Rolando C (1995) New insights into the molecular architecture of hardwood lignins by chemical degradative methods. Res Chem Intermed 21(3-5): 397-412.
13. Boerjan W, Ralph J, Baucher M (2003) Lignin biosynthesis. Ann Rev Plant Biol 54: 519-546.
14. 31P and 2D NMR spectroscopy. The occurrence of ester bonds and α-O-4 substructures. J Agr Food Chem 45: 1212-1219.
15. Ralph J, Hatfield RD, Quideau S, Helm RF, Grabber JH, Jung HJG (1994) Pathway of p-coumaric acid incorporation into maize lignin as revealed by NMR. J Am Chem Soc 116(21): 9448-9456.
16. Li J, Henriksson G, Gellerstedt G (2007) Lignin depolymerization/repolymerization and its critical role for delignification of aspen wood by steam explosion. Bioresour Technol 98: 3061-3068.
17. Kaparaju P, Felby C (2010) Characterization of lignin during oxidative and hydrothermal pretreatment processes of wheat straw and corn stover. Bioresour Technol 101: 3175-3181.
18. Buchala AJ, Wilkie KCB (1973) Total hemicelluloses from wheat at different stages of growth. Phytochemistry 12: 499-505.
19. Garrote G, Domínguez H, Parajó JC (1999) Hydrothermal processing of lignocellulosic materials. Holz als Roh- und Werkst 57: 191-202.
20. Scalbert A, Monties B, Lallemand J-Y, Guittet E, Rolando C (1985) Ether linkage between phenolic acids and lignin fractions from wheat straw. Phytochemistry 24(6): 1359-1362.
21. Sjöström E (1993) Wood Chemistry: fundamentals and applications, 2nd edn. Academic Press, Inc., San Diego.
22. Fry SC, Miller JG (1989) Toward a working model of the growing plant cell wall: phenolic cross-linking reaction in the primary cell walls of dicotyledons. In: Lewis NG, Paice MG (eds) Plant cell wall polymers: biogenesis and biodegradation, Symposium Series 399. American Chemical Society, Washington, D. C., pp 33-46.
23. Ralph J (2010) Hydroxycinnamates in lignification. Phytochem Rev 9: 65-83.
24. Ralph J, Grabber JH, Hatfield RD (1995) Lignin-ferulate cross-links in grasses - active incorporation of ferulate polysaccharide esters into ryegrass lignins. Carbohydr Res 275(1): 167-178.
25. Ralph J, Quideau S, Grabber JH, Hatfield RD (1994) Identification and synthesis of new ferulic acid dehydrodimers present in grass cell-walls. J Chem Soc Perk T 1(23): 3485-3498.
26. Bunzel M, Heuermann B, Kim H, Ralph J (2008) Peroxidase-catalyzed oligomerization of ferulic acid esters. J Agr Food Chem 56: 10368-10375.
27. Bunzel M, Ralph J, Funk C, Steinhart H (2003) Isolation and identification of a ferulic acid dehydrotrimer from saponified maize bran insoluble fiber. Eur Food Res Technol 217(2): 128-133.
28. Quideau S, Ralph J (1997) Lignin-ferulate cross-links in grasses 4. Incorporation of 5-5-coupled dehydrodiferulate into synthetic lignin. J Chem Soc Perk T 1 1(16): 2351-2358.
29. Hatfield RD, Ralph J, Grabber JH (1999) Cell wall cross-linking by ferulates and diferulates in grasses. J Sci Food Agr 79(3): 403-407.
30. Mueller-Harvey I, Hartley RD, Harris PJ, Curzon EH (1986) Linkage of p-coumaryl and feruloyl groups to cell wall polysaccharides of barley straw. Carbohydr Res 148: 71-85.
31. Bunzel M, Ralph J, Lu F, Hatfield RD, Steinhart H (2004) Lignins and ferulate-coniferyl alcohol cross-coupling products in cereal grains. J Agr Food Chem 52(21): 6496-6502.
32. Grabber JH, Ralph J, Hatfield RD (2002) Model studies of ferulate-coniferyl alcohol cross-product formation in primary maize walls: implications for lignification in grasses. J Agr Food Chem 50(21): 6008-6016.
33. Iiyama K, Lam TBT, Stone BA (1990) Phenolic acid bridges between polysaccharides and lignin in wheat internodes. Phytochemistry 29: 733-737.
34. Jacquet B, Pollet B, Lapierre C, Mhamdi F, Rolando C (1995) New ether-linked ferulic acid-coniferyl alcohol dimers identified in grass straws. J Agr Food Chem 43: 2746-2751.
35. Ralph J, Bunzel M, Marita JM, Hatfield R, Lu F, Kim H et al (2004) Peroxidase-dependent cross-linking reactions of p-hydroxycinnamates in plant cell walls. Phytochem Rev 3: 79-96.
36. Bunzel M, Ralph J, Kim H, Lu FC, Ralph SA, Marita JM et al (2003) Sinapate dehydrodimers and sinapate-ferulate heterodimers in cereal dietary fiber. J Agr Food Chem 51(5): 1427-1434.
37. Lu F, Ralph J (1999) Detection and determination of p-coumaroylated units in lignins. J Agr Food Chem 47(5): 1988-1992.
38. Ralph J, Landucci L (2010) NMR of lignins. In: Heitner C, Dimmel DR, Schmidt JA (eds) Lignin and Lignans: advances in chemistry. CRC Press (Taylor & Francis Group), Boca Raton, pp 137-234.
39. Sluiter A (2004) Determination of structural carbohydrates and lignin in biomass. http://www. nrel. gov/biomass/analytical_procedures. html. National Renewable Energy Laboratory (NREL) Analytical Procedures.
40. Kristensen JB, Thygesen LG, Felby C, Jørgensen H, Elder T (2008) Cell-wall structural changes in wheat straw pretreated for bioethanol production. Biotechnol Biofuels 1(5): 1-9.
41. Ralph SA, Ralph J, Landucci LL (2004) NMR database of lignin and cell wall model compounds, http://ars. usda. gov/Services/docs. htm?docid=10491.
42. 5. Org Biomol Chem 8(3): 576-591.
43. Sun XF, Sun R, Fowler P, Baird MS (2005) Extraction and characterization of original lignin and hemicelluloses from wheat straw. J Agr Food Chem 53: 860-870.
44. 13C NMR spectroscopy. Carbohydr Res 329(4): 807-815.
45. Selig MJ, Viamajala S, Decker SR, Tucker MP, Himmel ME, Vinzant TB (2007) Deposition of lignin droplets produced during dilute acid pretreatment of maize stems retards enzymatic hydrolysis of cellulose. Biotechnol Prog 23: 1333-1339.
46. Mosier NS, Hendrickson R, Brewer M, Ho N, Sedlak M, Dreshel R et al (2005) Industrial scale-up of pH-controlled liquid hot water pretreatment of corn fiber for fuel ethanol production. Appl Biochem Biotechnol 125: 77-97.
47. Donohoe BS, Tucker MP, Davis M, Decker SR, Himmel ME, Vinzant TB (2007) Tracking lignin coalescence and migration through plant cell walls during pretreatment. 29th Symposium on Biotechnology for Fuels and Chemicals. Denver, CO.
48. Hansen MA, Kristensen JB, Felby C, Jørgensen H (2011) Pretreatment and enzymatic hydrolysis of wheat straw (Triticum aestivum L.) - the impact of lignin relocation and plant tissues on enzymatic accessibility. Bioresour Technol 102: 2804-2811.
49. Kabel MA, Bos G, Zeevalking J, Voragen AGJ, Schols HA (2007) Effect of pretreatment severity on xylan solubility and enzymatic breakdown of the remaining cellulose from wheat straw. Bioresour Technol 98: 2034-2042.
50. Grethlein HE (1985) The effect of pore size distribution on the rate of enzymatic hydrolysis of cellulosic substrates. Nat Biotechnol 3(2): 155-160.
51. Chundawat SPS, Donohoe BS, da Costa SL, Elder T, Agarwal UP, Lu F et al (2011) Multi-scale visualization and characterization of lignocellulosic plant cell wall deconstruction during thermochemical pretreatment. Energy Environ Sci. doi: 10. 1039/c1030ee00574f.
52. Han G, Deng J, Zhang S, Bicho P, Wu Q (2010) Effect of steam explosion treatment on characteristics of wheat straw. Ind Crop Prod 31(1): 28-33.
53. Ralph J, Marita JM, Ralph SA, Hatfield R, Lu F, Ede RM et al (1999) Solution-state NMR of lignins. In: Argyropoulos DS, Rials T (eds) Advances in lignocellulosics characterization. TAPPI Press, Atlanta, pp 55-108.
54. Akiyama T, Kim H, Dixon RA, Ralph J (2007) Dibenzodioxocin structures involving p-hydroxyphenyl units in C3H down-regulated lignin. In: 10th International Congress on Biotechnology in the Pulp and Paper Industry. Madison, WI, p 71.
55. Ämmälahti E, Brunow G, Bardet M, Robert D, Kilpeläinen I (1998) Identification of side-chain structures in a poplar lignin using three-dimensional HMQC-HOHAHA NMR spectroscopy. J Agr Food Chem 46(12): 5113-5117.
56. Karhunen P, Rummakko P, Sipilä J, Brunow G, Kilpeläinen I (1995) Dibenzodioxocins; a novel type of linkage in softwood lignins. Tetrahedron Lett 36: 169-170.
57. Karhunen P, Rummakko P, Pujunen A, Brunow G (1996) Synthesis and crystal structure determination of model compounds for the dibenzodioxocine structure occurring in wood lignins. J Chem Soc Perk T 1(18): 2303-2308.
58. Stewart JJ, Akiyama T, Chapple C, Ralph J, Mansfield SD (2009) The effects on lignin structure of overexpression of ferulate 5-hydroxylase in hybrid poplar. Plant Physiol 150: 621-635.
59. Wagner A, Donaldson L, Kim H, Phillips L, Flint H, Steward D et al (2009) Suppression of 4-coumarate-CoA ligase in the coniferous gymnosperm Pinus radiata. Plant Physiol 149(1): 370-383.
60. Yelle DJ, Ralph J, Frihart CR (2011) Delineating pMDI model reactions with loblolly pine via solution-state NMR spectroscopy. Part 2. Non-catalyzed reactions with the wood cell wall. Holzforschung 65: 145-154.
61. Zhang LM, Gellerstedt G (2007) Quantitative 2D HSQC NMR determination of polymer structures by selecting suitable internal standard references. Magn Reson Chem 45: 37-45.
62. Koskela H, Heikkilä O, Kilpeläinen I, Heikkinen S (2010) Quantitative two-dimensional HSQC experiment for high magnetic field NMR spectrometers. J Magn Reson 202: 24-33.
63. Kupče E, Freeman R (2007) Compensated adiabatic inversion pulses: broadband INEPT and HSQC. J Magn Reson 187: 258-265.
64. Lundquist K, Lundgren R (1972) Acid degradation of lignin. Part VII. The cleavage of ether bonds. Acta Chem Scand 26(5): 2005-2023.
65. Reicher F, Corrêa JBC, Gorin PAJ (1984) Location of O-acetyl groups in the acidic d-xylan of Mimosa scabrella (bracatinga). A study of O-acetyl group migration. Carbohydr Res 135: 129-140.
66. Çetinkol ÖP, Dibble DC, Cheng G, Kent MS, Knierim B, Auer M et al (2010) Understanding the impact of ionic liquid pretreatment on eucalyptus. Biofuels 1: 33-46.
67. Ede RM, Brunow G, Poppius K, Sundquist J, Hortling B (1988) Formic acid/peroxyformic acid pulping. 1. Reactions of β-aryl ether model compounds with formic acid. Nord Pulp Pap Res J 3(3): 119-123.
68. Nimz HH, Robert D (1985) 13C NMR spectra of acetic acid lignins. In: International Symposium on Wood and Pulping Chemistry. Vancouver, B. C., p 267.
69. Sarkanen KV (1980) Acid catalyzed delignification of lignocellulosics in organic solvents. In: Sarkanen KV, Tillman DA (eds) Progress in biomass conversion, vol 2. Academic, New York, pp 127-144.
70. Shimada K, Hosoya S, Tomimura Y (1991) Delignification with organic acids. In: International Symposium on Wood and Pulping Chemistry. TAPPI Press, Melbourne, pp 183-188.