Isolation and analysis of lignin-carbohydrate complexes preparations with traditional and advanced methods: A review

Studies in Natural Products Chemistry

Volumn 42, Issue 1, 2014, Pages 83-115

  Balakshin, Mikhail ^a   Capanema, Ewellyn ^a   Berlin, Alex ^b  

^a Renmatix   (United States)

^b Novozymes Biotech Inc   (United States)

Author keywords

HSQC NMR technique; Lignin; Lignin carbohydrate complex; NMR; Polysaccharides; Quantitative 13C NMR

Indexed keywords

EID: 84897678495     PISSN: 15725995     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-444-63281-400004-5     Document Type: Review

References (100)

1. M. Lewin, and I.S. Goldstein Wood Structure and Composition 1991 Marcel Dekker, Inc. New York, Basel, Hong Kong
2. D. Fengel, and G. Wegener Wood Chemistry, Ultrastructure, Reactions 1984 Walter de Gruyter Berlin
3. R.L. Whistler, and C.-C. Chen M. Lewin, I.S. Goldstein, Wood Structure and Composition 1991 Marcel Dekker, Inc. New York, Basel, Hong Kong 287 319
4. C.-L. Chen M. Lewin, I.S. Goldstein, Wood Structure and Composition 1991 Marcel Dekker, Inc. New York, Basel, Hong Kong 183 261
5. E. Adler Wood Sci. Technol. 11 1977 169 218
6. A. Sakakibara D.N.-S. Hon, N. Shiraishi, Wood and Cellulose Chemistry 1991 Marcel Dekker Inc. New York 113 175
7. K.V. Sarkanen, and C.H. Ludwig Lignins. Occurrence, Formation, Structure and Reactions 1971 John Wiley & Sons New York, Chichester, Brisbane, Toronto, Singapore
8. B.B. Hallac, and A.J. Ragauskas Biofuel Bioprod. Bioref. 5 2011 215 225
9. T.E. Timell Adv. Carbohydr. Chem. 20 1965 409 483
10. B. Lindberg, K.-G. Rosell, and S. Svensson Svensk Papperstidn. 76 1973 383
11. L. Kenne, K.-G. Rosell, and S. Svensson Carbohydr. Res. 44 1975 69 76
12. S. Johnson, and S. Samuelson Anal. Chem. Acta 36 1966 1 11
13. H.O. Bouveng Acta Chem. Scand. 15 1961 87 95
14. K. Freudenberg K. Freudenberg, A.C. Neish, Constitution and Biosynthesis of Lignin 1968 Springer-Verlag Berlin, Heidelberg, New York 93 94
15. J. Ralph, K. Lundquist, G. Brunow, F. Lu, H. Kim, P.F. Schatz, J.M. Marita, R. Hatfield, S.A. Ralph, J.H. Christensen, and W. Boerjan Phytochem. Rev. 3 2004 29 60
16. M.Yu. Balakshin, E.A. Capanema, and H.-m. Chang T. Hu, Characterization of Lignocellulosics 2008 Blackwell Oxford, UK 148 166
17. O.P. Grushnikov, and V.V. Elkin Achievements and Problems in Lignin Chemistry (in Russian) 1973 Science Moscow
18. T. Koshijima, and T. Watanabe Association Between Lignin and Carbohydrates in Wood and Other Plant Tissues 2003 Springer-Verlag Berlin, Heidelberg
19. R.F. Helm W.G. Glasser, R.A. Northey, T.P. Schultz, Lignin: Historical, Biological, and Material Perspectives ACS Symposium Series vol. 742 2000 American Chemical Society Washington, DC 161 171
20. J. Obst Tappi 65 1982 109 112
21. M.Yu. Balakshin, E.A. Capanema, H. Gracz, H.-m. Chang, and H. Jameel Planta 233 2011 1097 1110
22. M. Lawoko, G. Henriksson, and G. Gellerstedt Biomacromolecules 6 2005 3467 3473
23. A. Björkman Svensk Papperstidn. 60 1957 243 251
24. A. Björkman Svensk Papperstidn. 59 1956 477 485
25. M.Yu. Balakshin, D.V. Evtuguin, C. Pascoal Neto, A.M.S. Silva, P.M. Domingues, and F.M.L. Amado Proceedings of the 11th International Symposium on Wood Pulping Chemistry, vol. 1, Nice, France 2001 103 110
26. M.Yu. Balakshin, D.V. Evtuguin, and C. Pascoal Neto Proceedings of the 7th Brazilian Symposium on Chemistry of Lignin and other Wood Components, Belo Horizonte, MG, Brazil 2001 53 60
27. E.A. Capanema, M.Yu. Balakshin, J.F. Kadla, and H.-m. Chang O Papel N5 2007 74 79
28. E.A. Capanema, M.Yu. Balakshin, R. Katahira, H.-m. Chang, and H. Jameel Proceedings of the 14th ISWFPC, Durban, South Africa 2007 CD-ROM
29. M.Yu. Balakshin, E.A. Capanema, and H.-m. Chang Holzforschung 61 2007 1 7
30. J. Azuma, N. Takahashi, and T. Koshijima Carbohydr. Res. 93 1981 91 104
31. J.C. Pew Tappi 40 1957 553 558
32. J.C. Pew, and P. Weyna Tappi 45 1962 247 256
33. H.-m. Chang, E.B. Cowling, W. Brown, E. Adler, and G. Miksche Holzforschung 29 1975 153 159
34. E.A. Capanema, M.Yu. Balakshin, and J.F. Kadla J. Agric. Food Chem. 53 2005 9639 9649
35. H. Aimi, Y. Matsumoto, and G. Meshitsuka J. Wood Sci. 50 2004 415 421
36. O. Eriksson, and B.O. Lindgren Svensk Papperstidn. 80 1977 59 63
37. A. Fujimoto, Y. Matsumoto, G. Meshitsuka, and H.-m. Chang J. Wood Sci. 51 2005 89 91
38. Z. Hu, T.-F. Yeh, H.-m. Chang, Y. Matsumoto, and J.F. Kadla Holzforschung 60 2006 389 397
39. M.Yu. Balakshin, E.A. Capanema, H.-m. Chang, and H. Jameel Proceedings of the 14th ISWFPC, Durban, South Africa 2007 CD-ROM
40. A. Enoki, F. Yaku, and T. Koshijima Holzforschung 37 1983 135 141
41. T. Juhást, Z. Szengyel, K. Réczey, M. Siika-Aho, and L. Viikari Process Biochem. 40 2005 3519 3525
42. http://www.brenda-enzymes.org (accessed 11.12.13).
43. F. Lu, and J. Ralph Plant J. 35 2003 535 544
44. Z. Wang, T. Yokoyama, H.-m. Chang, and Y. Matsumoto J. Agric. Food Chem. 57 2009 6167 6170
45. M. Balakshin, E.A. Capanema, H.-m. Chang, and H. Jameel Proceedings of the 17th ISWPC, Vancouver, Canada 2013 http://epaccontrol.com/online/iswfpc2013/
46. T. Yamasaki, S. Hosoya, C.-L. Chen, J.S. Gratzl, and H.-m. Chang Proceedings of the 9th ISWPC, Stockholm, Sweden, vol. II 1981 34 42
47. H.-m. Chang S.Y. Lin, C.W. Dence, Methods in Lignin Chemistry 1992 Springer-Verlag Heidelberg, Berlin, New York 71 74
48. M.Yu. Balakshin, E.A. Capanema, C.-L. Chen, and H. Gracz J. Agric. Food Chem. 51 2003 6116 6127
49. E.A. Capanema, M.Yu. Balakshin, and C.-L. Chen Holzforschung 58 2004 464 472
50. E.A. Capanema, M.Yu. Balakshin, C.-L. Chen, J.S. Gratzl, and H. Gracz Proceedings of the 7th Brazilian Symposium on Chemistry of Lignin and other Wood Components, Belo Horizonte, MG, Brazil 2001 61 68
51. E.A. Capanema, M.Yu. Balakshin, C.-L. Chen, K.L. Colson, and H.S. Gracz Proceedings of the 12th ISWPC, Wisconsin, USA 2003 179 182
52. A. Berlin, N. Gilkes, A. Kurabi, R. Bura, M. Tu, D. Kilburn, and J. Saddler Appl. Biochem. Biotechnol. 121-124 2005 163 170
53. A. Berlin, M. Balakshin, N. Gilkes, J. Kadla, V. Maximenko, S. Kubo, and J. Saddler J. Biotechnol. 125 2006 198 209
54. B.R. Scott, P. St-Pierre, J. Lavigne, N. Masri, T.C. White, J.J. Tomashek, US2010/0221778 A1, September 2, 2010.
55. K. Freudenberg, and G. Grion Chem. Ber. 92 1959 1355 1363
56. K. Freudenberg, and J.M. Harkin Chem. Ber. 93 1960 2814 2819
57. J.-P. Joseleau, and R. Kesraoui Holzforschung 40 1986 163 168
58. A. Barakat, H. Winter, C. Rondeau-Mouro, B. Saake, B. Chabbert, and B. Cathala Planta 226 2007 267 281
59. J.H. Grabber, J. Ralph, and R.D. Hatfield J. Agric. Food Chem. 50 2002 6008 6016
60. J. Ralph, R.D. Hatfield, S. Quideau, R.F. Helm, J.H. Grabber, and H.-J.G. Jung J. Am. Chem. Soc. 116 1994 9448 9456
61. K. Li, and R.F. Helm J. Agric. Food Chem. 43 1995 2098 2103
62. N. Terashima, S.A. Ralph, and L.L. Landucci Holzforschung 50 1996 151 155
63. M. Toikka, J. Sipila, A. Teleman, and G. Brunow J. Chem. Soc., Perkin Trans. 1 1998 3813 3818
64. M. Toikka, and G. Brunow J. Chem. Soc., Perkin Trans. 1 1999 1877 1883
65. T. Tokimatsu, T. Umezawa, and M. Shimada Holzforschung 50 1996 156 160
66. B. Košíková, D. Joniak, and L. Kosá ková Holzforschung 33 1979 11 14
67. Ö. Eriksson, D.A.I. Goring, and B.O. Lindgren Wood Sci. Technol. 14 1980 267 279
68. O. Karlsson, T. Ikeda, T. Kishimoto, K. Magara, Y. Matsumoto, and S. Hosoya J. Wood Sci. 50 2004 142 150
69. J.L. Minor J. Wood Chem. Technol. 2 1982 1 16
70. J.L. Minor J. Wood Chem. Technol. 6 1986 185 201
71. I. Iversen Wood Sci. Technol. 19 1985 243 251
72. I. Iversen, and S. Wannstörm Holzforschung 40 1986 19 22
73. T. Watanabe Wood Res. 76 1989 59 123
74. T. Watanabe, M. Karina, Y. Sudiyani, T. Koshijima, and M. Kuwahara Wood Res. 79 1993 13 22
75. T. Watanabe, and T. Koshijima Mokuzai Gakkaishi 35 1989 130 134
76. C. Schwager, O. Faix, J.O. Metzger, and J. Puls Proceedings of the 3rd EWLP, Stockholm, Sweden, August 28-31 1994 13 15
77. M.Yu. Balakshin, and E.A. Capanema Proceedings of the 13th ISWFPC, Auckland, New Zealand, vol. II 2005 353 360
78. N.N. Das, S.C. Das, and A.K. Mukherjee Carbohydr. Res. 127 1984 345 348
79. N. Terashima, Y. Seguchi, and D. Robert Holzforschung 45 Suppl. 1991 35 39
80. Y. Xie, S. Yasuda, H. Wu, and H. Liu J. Wood Sci. 46 2000 130 136
81. E.A. Capanema, M.Yu. Balakshin, and J.F. Kadla J. Agric. Food Chem. 52 2004 1850 1860
82. D.J. Yelle, J. Ralph, and C.R. Frihart Magn. Res. Chem. 46 2008 508 517
83. A. Teleman, J. Lundqvist, F. Tjerneld, H. Stalbrand, and O. Dahlman Carbohydr. Res. 329 2000 807 815
84. L. Zhang, and G. Gellerstedt Proceedings of the 6th European Workshop on Lignocellulosics and Pulp, Bordeaux, France 2000 7 10
85. S. Heikkinen, M.M. Toikka, T. Karhunen, and I.A. Kilpelainen J. Am. Chem. Soc. 125 2003 4362 4367
86. J. Ralph, T. Akiyama, H. Kim, F. Lu, P.F. Schatz, J.M. Marita, S.A. Ralph, M.S.S. Reddy, F. Chen, and R.A. Dixon J. Biol. Chem. 281 2006 8843 8853
87. D. Ibarra, M.I. Chavez, J. Rencoret, J.C. Del Rio, A. Gutierrez, J. Romero, S. Camarero, M.J. Martinez, J. Jumenez-Barbero, and A.T. Martinez J. Agric. Food Chem. 55 2007 3477 3490
88. L. Zhang, and G. Gellerstedt Magn. Res. Chem. 45 2007 37 45
89. T.-Q. Yuan, S.-N. Sun, F. Xu, and R.-C. Sun J. Agric. Food Chem. 59 2011 10604 10614
90. B. Henrissat Cellulose 3 1994 169 196
91. K.G. Johnson, and R.P. Overend Holzforschung 45 1991 469 475
92. K.G. Johnson, and R.P. Overend Holzforschung 46 1992 31 37
93. N.W. Ross, K.G. Johnson, C. Braun, C.R. MacKenzie, and H. Schneider Microb. Technol. 14 1992 90 95
94. P. Biely, J. Puls, and H. Schneider FEBS Lett. 186 1985 80 84
95. T.W. Jeffries C. Ratledge, Biodegradation of Lignin and Hemicelluloses 1994 Kluwer Academic Amsterdam 233 277
96. X. Li, W. Beeson, C. Phillips, M.A. Marletta, and J.H.D. Cate Structure 20 2012 1051 1061
97. A. Berlin, N. Gilkes, and J. Saddler 28th Symposium on Biotechnology for Fuels and Chemicals, Nashville, TN, USA, April 30-May 3, Oral Presentation #1A-04 2006
98. A. Berlin, V. Maximenko, N. Gilkes, and J. Saddler Biotechnol. Bioeng. 97 2007 287 296
99. A. Berlin, N. Gilkes, D. Kilburn, V. Maximenko, R. Bura, A. Markov, A. Skomarovsky, O. Okunev, A. Gusakov, D. Gregg, A. Sinitsyn, and J. Saddler Appl. Biochem. Biotechnol. 129-132 2006 528 545
100. A. Berlin, N. Gilkes, D. Kilburn, R. Bura, A. Markov, A. Skomarovsky, O. Okunev, A. Gusakov, V. Maximenko, D. Gregg, A. Sinitsyn, and J. Saddler Enzyme Microb. Technol. 37 2005 175 184