A FT-ICR MS study of lignin: Determination of an unusual structural repetitive unit in steam exploded lignin from wheat straw

Letters in Organic Chemistry

Volumn 8, Issue 6, 2011, Pages 436-446

  D'Auria, Maurizio ^a   Emanuele, Lucia ^a   Racioppi, Rocco ^a  

^a UNIVERSITY OF BASILICATA   (Italy)

Author keywords

13C NMR; 1H NMR; FT ICR MS; Gel permeation chromatography; Lignin; MALDI TOF; Steam explosion

Indexed keywords

EID: 79961043840     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017811796064386     Document Type: Article

References (67)

1. Boerjan, W.; Ralph, J.; Baucher, M. Lignin biosynthesis, Ann. Rev. Plant Biol. 2003, 54, 519-546. (Pubitemid 37400004)
2. Wayman, T.; Obiaga, T. The Modular Structure of Lignin, Can. J. Chem. 1974, 52, 2102-2110.
3. Falkehag, S. I. Synthesis of phenolic polymers, Appl. Polym. Symp. 1975, 28, 247-257.
4. Monties, B. Plant cell walls as fibrous lignocellulosic composites: relations with lignin structure and function, Anim. Feed Sci. Tech. 1991, 32, 159-175.
5. Gilardi, G.; Cass, A. E. G. Associative and colloidal behavior of lignin and implications for its biodegradation in vitro, Langmuir 1993, 9, 1721-1726. (Pubitemid 23714692)
6. Radotic, K.; Simic-Krstic, J.; Jeremic, M.; Trifunovic, M. A study of lignin formation at the molecular level by scanning tunneling microscopy, Biophys. J. 1994, 66, 1763-1767. (Pubitemid 24167929)
7. Radotic, K.; Tasic, M.; Jeremic, M.; Budimljia, Z.; Simic-Krstic, J.; Polzovic, A.; Bozovic, Z. Fractal analysis of STM images of lignin polymer obtained by in vitro synthesis, Gen. Physiol. Biophys. 2000, 19, 171-180.
8. Radotic, K.; Tasic, M.; Jeremic, M.; Budimlija, Z.; Simic-Krstic, J.; Polzovic, A.; Bozovic, Z. Fractal analysis of STM images of photochemical polymer of coniferyl alcohol. Gen. Physiol. Biophys. 2001, 20, 33-42. (Pubitemid 33617046)
9. Norgren, M.; Edlund, H.; Wgberg, L. Aggregation of Lignin Derivatives under Alkaline Conditions. Kinetics and Aggregate Structure, Langmuir 2002, 18, 2859-2865. (Pubitemid 35383861)
10. Contreras, S.; Gaspar, A. R.; Guerra, A.; Lucia, L. A.; Argyropoulos, D. S. Propensity of lignin to associate: light scattering photometry study with native lignins, Biomacromolecules 2008, 9, 3362-3369.
11. Donaldson, L. A. Mechanical constraints on lignin deposition during lignification Wood Sci. Technol. 1994, 28, 111-118.
12. Kosikova, B.; Zakutna, L.; Joniak, D. Investigation of the ligninsacharidic complex by electron microscopy, Holzforschung 1978, 32, 15-25.
13. Donaldson, L. A. Lignification and lignin topochemistry - an ultrastructural view Phytochemistry 2001, 57, 859-873. (Pubitemid 32607034)
14. Micic, M.; Jeremic, M.; Radotic, K.; Mavers, M.; Leblanc, R. M. A. Comparative Study of Enzymatically and Photochemically Polymerized Artificial Lignin Supramolecular Structures Using Environmental Scanning Electron Microscopy, J. Colloid Interf. Sci. 2000, 231, 190-194.
15. Micic, M.; Jeremic, M.; Radotic, K.; Mavers, M.; Leblanc, R. M. Visualization of artificial lignin supramolecular structures Scanning 2000, 22, 288-294. (Pubitemid 32102156)
16. Micic, M.; Radotic, K.; Jeremic, M.; Leblanc, R. M. Study of Self-Assembly of the Lignin Model Compound on Cellulose Model Substrate, Macromol. Biosci. 2003, 3, 100-106. (Pubitemid 36559514)
17. Shevchenko, S. M.; Bailey, G. W.; Yu, Y. S.; Akim, L. G. Nanoscale morphology of lignins and their chemical transformation products, Tappi J. 1996, 79, 227-237. (Pubitemid 126638143)
18. Shevchenko, S. M.; Yu, Y. S.; Akim, L. G.; Bailey, G. W. Comparing surface morphology of lignin-carbohydrate complex and humic substances: AFM/VR approach, Holzforschung 1998, 52, 149-156. (Pubitemid 128561930)
19. Constantino, C.; Dhanabalan, A.; Cotta, M. A.; Pereira-da-Silva, M. A.; Curvelo, A. A. S.; Oliveira, O. N. Atomic Force Microscopy (AFM) Investigation of Langmuir-Blodgett (LB) Films of Sugar Cane Bagasse Lignin, Holzforschung 2000, 54, 55-60. (Pubitemid 34043594)
20. Simola, J.; Malkavaara, P.; Alen, R.; Peltonen, J. Scanning probe microscopy of pine and birch kraft pulp fibres, Polymer 2000, 41, 2121-2126. (Pubitemid 30025574)
21. Micic, M.; Benitez, I.; Ruano, M.; Mavers, M., Jeremic, M., Radotic, K.; Moy, V.; Leblanc, R. M. Probing the lignin nanomechanical properties and lignin-lignin interactions using the atomic force microscopy, Chem. Phys. Lett. 2001, 347, 41-45. (Pubitemid 33642335)
22. Micic, M.; Radotic, K.; Benitez, I., Ruano, M.; Jeremic, M.; Moy, V.; Mabrouki, M.; Leblanc, R. M. Topographical characterization and surface force spectroscopy of the photochemical lignin model compound, Biophys. Chem. 2001, 94, 257-263. (Pubitemid 34136119)
23. Simola-Gustafsson, J.; Hortling, B.; Peltonen, J. Scanning probe microscopy and enhanced data analysis on lignin and elementalchlorine-free or oxygen-delignified pine kraft pulp, Colloid Polym. Sci. 2001, 279, 221-231. (Pubitemid 32219780)
24. Pasquini, D.; Balogh, D. T.; Antunes, P. A.; Constantino, C. J. L.; Curvelo, A. A. S.; Aroca, R. F.; Oliveira, O. N. Surface Morphology and Molecular Organization of Lignins in Langmuir..Blodgett Films, Langmuir 2002, 18, 6593-6596. (Pubitemid 35383293)
25. Gustafsson, J.,; Ciovica, L.; Peltonen, J. The ultrastructure of spruce kraft pulps studied by atomic force microscopy (AFM) and X-ray photoelectron spectroscopy (XPS), Polymer 2003, 44, 661-670. (Pubitemid 36083199)
26. Gellerstedt, G. Gel permeation chromatography, in: Lin, S. Y., Dence C. W. (Eds.), Methods in Lignin Chemistry, Springer-Verlag, Berlin, 1992, pp. 485-497.
27. Pla, F. Vapor pressure osmometry, in: Lin, S. Y., Dence C. W. (Eds.), Methods in Lignin Chemistry, Springer-Verlag, Berlin, 1992, pp. 509-524.
28. Guerra, A.; Gaspar, A. R.; Contreras, S.; Lucia, L. A., Crestini, C.; Argyropoulos, D. A. On the propensity of lignin to associate: a size exclusion chromatography study with lignin derivatives isolated from different plant species, Phytochemistry 2007, 68, 2570-2583. (Pubitemid 47451447)
29. Murano, E.; Toffanin, R.; Knutsen, S. H.; Focher, B., Rizzo, R.; Paoletti, S. Evaluation of steam explosion as pretreatment in agar extraction from Gracilaria dura (C. Agardh) J. Agardh (Gracilariaceae, Rhodophyta), J. Appl. Phycology 1993, 5, 417-424.
30. Overend, R. P.; Chornet, E. Fractionation of lignocellulosics by steam-aqueous pretreatments, Phil. Trans. R. Soc. Lond. 1987, A321, 523-536.
31. Ramos, L. P. The chemistry involved in the steam treatment of lignocellulosic materials, Quim. Nova 2003, 26, 863-871.
32. Sun, X. F.; Xu, F.; Sun, R. C.; Wang, Y. X.; Fowler, P., Baird, M. S. Characteristics of degraded cellulose obtained from steamexploded wheat straw, Carbohydr. Res. 2005, 340, 97-106. (Pubitemid 40023302)
33. Sun, X. F.; Xu, F.; Sun, R. C.; Wang, Y. X.; Fowler, P.; Baird, M. S. Characteristics of degraded hemicellulosic polymers obtained from steam exploded wheat straw, Carbohydr. Polym. 2005, 60, 15-26. (Pubitemid 40371050)
34. Glasser, W. G.; Wright, R. S. Steam-assisted biomass fractionation. II. Fractionation behavior of various biomass resources, Biomass Bioenergy 1998, 14, 219-235. (Pubitemid 28244480)
35. Chua, M. G. S.; Wayman, M. Characterization of autohydrolysis aspen (P. tremuloides) lignins. Part 1. Composition and molecular weight distribution of extracted autohydrolysis lignin, Can J. Chem. 1979, 57, 1141-1149.
36. Marchessault, R. H.; Coulombe, S.; Morikawa, H.; Robert, D. Characterization of aspen exploded wood lignin, Can. J. Chem. 1982, 60, 2372-2382.
37. Argyropoulos, D. S. Quantitative Phosphorus-31 NMR analysis of six soluble lignins, J. Wood Chem. Technol. 1994, 14, 65-82.
38. Heitz, M.; Wu, G.; Lapointe, J.; Rubio, M. Hydrolytic depolymerization of a steam explosion lignin, J. Wood Chem. Technol. 1995, 15, 515-528. (Pubitemid 126008447)
39. Bonini, C.; D'Auria, M.; D'Alessio, L.; Mauriello, G.; Viggiano, D.; Zimbardi, F. Singlet oxygen degradation of lignin, J. Photochem. Photobiol. A 1998, 113, 119-124. (Pubitemid 128176559)
40. Bonini, C.; D'Auria, M.; Mauriello, G.; Viggiano, D.; Zimbardi, F. Singlet oxygen degradation of lignin in the pulp, J. Photochem. Photobiol. A 1998, 118, 107-110. (Pubitemid 128346937)
41. Bonini, C.; D'Auria, M.; Mauriello, G.; Pucciariello, R.; Teghil, R.; Tofani, D.; Viggiani, L.; Viggiano, D.; Zimbardi, F. Graft copolymers of lignin from straw with 1-ethenylbenzene: synthesis and characterization, J. Appl. Polym. Sci. 2001, 79, 72-79. (Pubitemid 32074485)
42. Bonini, C.; Carbone, A., D'Auria, M. Singlet oxygen mediated degradation of lignin - a kinetic study, Photochem. Photobiol. Sci. 2002, 1, 407-411. (Pubitemid 37069753)
43. Bonini, C.; D'Auria, M.; Ferri, R.; Pucciariello, R.; Sabia, A. R. Graft copolymers of lignin with electron poor alkenes, J. Appl. Polym. Sci. 2003, 90, 1163-1171. (Pubitemid 37126649)
44. Bonini, C.; D'Auria, M.; Emanuele, L.; Ferri, R.; Pucciariello, R.; Sabia, A. R. Polyurethanes and polyesters from lignin, J. Appl. Polym. Sci. 2005, 98, 1451-1456. (Pubitemid 41625235)
45. D'Auria, M.; Bonini, C.; Emanuele, L.; Ferri, R. Singlet-oxygen mediated degradation of lignin - Isolation of oxidation products from steam-exploded lignin from straw, J. Photochem. Photobiol. A 2002, 147, 153-156
46. Nakamura, Y.; Sawada, T.; Kuno, K.; Nakamoto, Y. Resinification of woody lignin and its characteristics on safety and biodegradation, J. Chem. Eng. Jpn 2001, 34, 1309-1312. (Pubitemid 33071675)
47. Robert, D.; Bardet, M.; Lapierre, C.; Gellerstedt, G. Structural changes in aspen lignin during steam explosion treatment, Cell. Chem. Technol. 1988, 22, 221-230.
48. Himmel, M. E.; Tatsumoto, K.; Grohmann, K.; Johnson, D. K.; Chum, H. L. Molecular weight distribution of aspen lignins from conventional gel permeation chromatography, universal calibration and sedimentation equilibrium, J. Chromatogr. 1990, 498, 93-104. (Pubitemid 20036047)
49. Hemmingson, J. A. Structural aspects of lignins from Eucalyptus regnans wood steam exploded by the Iotech and Siropulper processes, J. Wood Chem. Technol. 1985, 5, 513-534.
50. Montané, D.; Salvadó, J., Farriol, X. Fractionation of wheat straw via steam-explosion pretreatment. Characteristics of the lignin obtained by alkali delignification of the steamed straw, Holzforschung 1997, 51, 135-141. (Pubitemid 127556947)
51. 2-catalyzed steam explosion and enzymatic hydrolysis of Eucalyptus viminalis wood chips, J. Agric. Food Chem. 1999, 47, 2295-2302. (Pubitemid 29325113)
52. Hemmingson, J. A. Steam-explosion lignins: fractionation, composition, structure and extractives, J. Wood Chem. Technol. 1987, 7, 527-553.
53. 31P-NMR, FTIR and wet chemical methods, Holzforschung 1994, 48, 387-394.
54. 13C NMR analysis of lignins with internal standards, J. Agric. Food Chem. 2001, 49, 3573-3578. (Pubitemid 32822660)
55. 13C NMR study of the effect of steam explosion processes on wood composition and structure, J. Wood Chem. Technol. 1985, 5, 159-188.
56. 13C-NMR characterization of steam exploded poplar hood, J. Wood Chem. Technol. 1987, 7, 215-228.
57. Metzger, J. O.; Bicke, C.; Faix, O.; Tuszynski, W.; Angermann, R.; Karas, M.; Strupat, K. Matrix-Assisted Laser Desorption Mass Spectrometry of Lignins, Angew. Chem. Int. Ed. Engl. 1992, 31, 762-764.
58. Jacobs, A.; Dahlman, O. Absolute molar mass of lignins by size exclusion chromatography and MALDI-TOF mass spectroscopy, Nord. Pulp Pap. Res. J. 2000, 15, 120-127.
59. Marshall, A. G.; Hendrickson, C. L.; Jackson, G. S. Fourier transform ion cyclotron resonance mass spectrometry: a primer, Mass. Spectrom. Rev. 1998, 17, 1-35. (Pubitemid 128629493)
60. Szuleiko, J. E.; Solouki, T. Potential analytical applications of interfacing a GC to an FT-ICR MS: fingerprinting complex sample matrixes, Anal. Chem. 2002, 74, 3434-3442. (Pubitemid 34764950)
61. Stenson, A. C.; Landing, W. M.; Marshall, A. G.; Cooper, W. T. Ionization and fragmentation of humic substances in electrospray ionization Fourier transform-ion cyclotron resonance mass spectrometry, Anal. Chem. 2002, 74, 4397-4409. (Pubitemid 35006427)
62. Solouki, T.; Freitas, M. A.; Alomary, A. Gas-phase hydrogen/deuterium exchange reactions of fulvic acids: an electrospray ionization Fourier transform ion cyclotron resonance mass spectral study, Anal. Chem. 1999, 71, 4719-4726.
63. Kujawinski, E. B.; Hatcher, P. G.; Freitas, M. A. High-resolution Fourier transform ion cyclotron resonance mass spectrometry of humic and fulvic acids: improvements and comparisons, Anal. Chem. 2002, 74, 413-419. (Pubitemid 34072708)
64. Srzić, D.; Martinović, S.; Tolić, L. P.; Shevchenko, S. M.; Klasinc, L. Laser desporption Fourier-transform mass spectrometry of lignins, Rapid Commun. Mass Spectrom. 1995, 9, 245-249.
65. Srzić, D.; Martinović, S.; Tolić, L. P.; Kezele, N.; Kazazić, S.; Senković, L.; Shevchenko, S. M.; Klasinc, L. Laser Desorption Fourier Transform Mass Spectrometry of Natural Polymers, Rapid Commun. Mass Spectrom. 1996, 10, 580-582. (Pubitemid 126814029)
66. Pucciariello, R.; Villani, V.; Bonini, C.; D'Auria, M.; Vetere, T. Physical properties of straw lignin-based polymer blends, Polymer 2004, 45, 4159-4169. (Pubitemid 38638180)
67. Wu, Z.; Rodgers, R. P.; Marshall, A. G. Two- and Three- Dimensional van Krevelen Diagrams: A Graphical Analysis Complementary to the Kendrick Mass Plot for Sorting Elemental Compositions of Complex Organic Mixtures Based on Ultrahigh-Resolution Broadband Fourier Transform Ion Cyclotron Resonance Mass Measurements, Anal. Chem. 2004, 76, 2511-2516. (Pubitemid 38585717)