Parameters affecting in vitro monolignol couplings during dehydrogenative polymerization in the presence of peroxidase and H2O2

Hyewon Hwang; Sun-Joo Moon; Keehoon Won; Yong Hwan Kim; Joon Weon Choi

Journal of Industrial and Engineering Chemistry, Vol.26, 390-395, June, 2015

DOI10.1016/j.jiec.2014.12.014 Export Citation

Parameters affecting in vitro monolignol couplings during dehydrogenative polymerization in the presence of peroxidase and H2O2

Hyewon Hwang, Sun-Joo Moon, Keehoon Won¹, Yong Hwan Kim², and Joon Weon Choi^{3, †}

Department of Forest Sciences and Research Institute for Agriculture and Life Science, Seoul National University, 599 Gwanak-ro, Gwanak-gu, Seoul 151-921, South Korea
¹Department of Chemical and Biochemical Engineering, Dongguk University-Seoul, 26 Pil-dong 3-ga, Jung-gu, Seoul 100-715, South Korea
²Department of Chemical Engineering, Kwangwoon University, Seoul 139-701, South Korea
³Graduate School of International Agricultural Technology and Institute of Green-Bio Science and Technology, Seoul National University, Pyeongchang 232-916, South Korea

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Dehydrogenative polymers (DHP) were synthesized by end-wise coupling (Zutropfverfahren) with coniferyl alcohol in a mixture of organic solvents (isopropyl alcohol, dioxane, acetonitrile) and buffer with various ratios in the presence of horse radish peroxidase and H2O2. When the ratio of organic solvent to buffer increased, DHP yield decreased from 78.3% to 42.7% in dioxane/buffer and from 77.8% to 43.2% in acetonitrile/buffer, whereas DHP yield in isopropyl alcohol/buffer was almost constant from 78.4% to 74.0%. The effects of adding organic solvents to the buffer were also evaluated with GPC analysis of DHP and frequency of β-O-4 linkage in DHP by DFRC analysis.

Keywords:Dehydrogenative polymerization;Lignin;Solvent effect;β-O-4 Formation;Steric hindrance

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Cathala B, et al., Polym. Degrad. Stabil., 65 (1998)
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Putter J, Becker R, in: Bergmeyer HU (Ed.), Peroxidases in Methods of Enzymatic Analysis, vol. 3, Verlag-Chemie, Weinheim, Germany, 1983.
Lu F, Ralph J, J. Agric. Food Chem., 45(7), 2590 (1997)
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Erickson M, Larsson S, Miksche G, Acta Chem. Scand., 27(3), 903 (1973)
Nimz H, Angew. Chem.-Int. Edit., 13(5), 313 (1974)
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Shigematsu M, Masamoto H, J. Wood Sci., 54, 308 (2008)
Bjorkman A, Sven. Papperstidn., 59, 477 (1956)
Ikeda R, Uyama H, Kobayashi S, Macromolecules, 29(8), 3053 (1996)
Iwahara K, Honda Y, Watanabe T, Kuwahara M, Appl. Microbiol. Biotechnol., 54(1), 104 (2000)
Ikeda R, Sugihara J, Uyama H, Kobayashi S, Polym. Int., 47(3), 295 (1998)
Kobayashi T, Taguchi H, Shigematsu M, Tanahashi M, J. Wood Sci., 51, 607 (2005)
Moon SJ, Kim KH, Eom IY, Lee SM, Kim YH, Choi JW, J. Wood Sci. Technol., 38, 223 (2010)
Moon SJ, Kwon M, Choi DH, Won KH, Kim YH, Choi IG, Choi JW, Phytochemistry, 82, 15 (2012)
Ostergaard L, Teilum K, Mirza O, Mattsson O, Petersen M, Welinder KG, Mundy J, Gajhede M, Henriksen A, Plant Mol. Biol., 44, 231 (2000)

[Related Articles]

[1] Lynd L, Cushman J, Nichols R, Wyman C, Science, 251, 1318 (1991)

[2] Hill J, Nelson E, Tilman D, Polasky S, Tiffany D, Proc. Natl. Acad. Sci. U.S.A., 103, 11206 (2006)

[3] Landucci LL, J. Wood Chem. Technol., 20, 243 (2000)

[4] Brunow G, in: Hofrichter M, Steinbuchel A (Eds.), Humic Substances and Coal, Willey-VHC, Weinheim, Germany, 2001, p. 89.

[5] Khmelniysky YL, Levashov AV, Klyachko NL, Martinek K, Enzyme Microb. Technol., 10, 710 (1988)

[6] Torres E, Tinoco R, Vazquez-Duhalt R, J. Biotechnol., 49, 59 (1996)

[7] Tanahashi M, Takeuchi H, Higuchi T, Wood Res., 61, 44 (1967)

[8] Mikiji S, Hiroshi M, Jpn. Wood Res. Soc., 54, 308 (2008)

[9] Obiaga TI, Lignin Molecular Weight and Molecular Weight Distribution During alkaline Pulping of Wood, Univ. of Toronto, 1972 (Dissertation).

[10] Higuchi T, Ogino K, Tanahashi M, Wood Res., 51, 1 (1971)

[11] Cathala B, et al., Polym. Degrad. Stabil., 65 (1998)

[12] Quideau S, Ralph J, J. Agric. Food. Chem., 40(7), 1108 (1992)

[13] Putter J, Becker R, in: Bergmeyer HU (Ed.), Peroxidases in Methods of Enzymatic Analysis, vol. 3, Verlag-Chemie, Weinheim, Germany, 1983.

[14] Lu F, Ralph J, J. Agric. Food Chem., 45(7), 2590 (1997)

[15] Gupta MN, Batra R, Tyagi R, Sharma A, Biotechnol. Prog., 13(3), 284 (1997)

[16] Batra R, Gupta MN, Biotechnol. Lett., 16(10), 1059 (1994)

[17] Butler LG, Enzyme Microb. Technol., 1(4), 253 (1979)

[18] Erickson M, Larsson S, Miksche G, Acta Chem. Scand., 27(3), 903 (1973)

[19] Nimz H, Angew. Chem.-Int. Edit., 13(5), 313 (1974)

[20] Kishimoto T, Uraki Y, Ubukata M, Org. Biomol. Chem., 4(7), 1343 (2006)

[21] Shigematsu M, Masamoto H, J. Wood Sci., 54, 308 (2008)

[22] Bjorkman A, Sven. Papperstidn., 59, 477 (1956)

[23] Ikeda R, Uyama H, Kobayashi S, Macromolecules, 29(8), 3053 (1996)

[24] Iwahara K, Honda Y, Watanabe T, Kuwahara M, Appl. Microbiol. Biotechnol., 54(1), 104 (2000)

[25] Ikeda R, Sugihara J, Uyama H, Kobayashi S, Polym. Int., 47(3), 295 (1998)

[26] Kobayashi T, Taguchi H, Shigematsu M, Tanahashi M, J. Wood Sci., 51, 607 (2005)

[27] Moon SJ, Kim KH, Eom IY, Lee SM, Kim YH, Choi JW, J. Wood Sci. Technol., 38, 223 (2010)

[28] Moon SJ, Kwon M, Choi DH, Won KH, Kim YH, Choi IG, Choi JW, Phytochemistry, 82, 15 (2012)

[29] Ostergaard L, Teilum K, Mirza O, Mattsson O, Petersen M, Welinder KG, Mundy J, Gajhede M, Henriksen A, Plant Mol. Biol., 44, 231 (2000)