Link to Research
Renewables > Bioenergy

Efficient Biomass Conversion: Delineating the Best Lignin Monomer-Substitutes

Start Date: December 2008

Investigators

John Ralph, Xuejun Pan, and Sara Patterson, University of Wisconsin, Madison

Annual Reports

Publications

  • Liu, B., M. A. Butenko, C-L. Shi, J. L. Bolivar, P. Winge, G-E. Stenvik, A. K. Vie, M. E. Leslie, T. Brembu, and W. Kristiansen. Nevershed and Inflorescence deficient in abscission are differentially required for cell expansion and cell separation during floral organ abscission in arabidopsis thaliana. Journal of Experimental Botany: ert232 (2013).
  • Ress, D. K. and J. Ralph. “Synthesis of 3-O-vanillate and 3-O-ferulate esters of (-)-epicatechin.” Journal of Agricultural and Food Chemistry, in revision.
  • Zhu, Y., A. Mohammadi, and J. Ralph. “Facile Synthesis of 4-Hydroxycinnamaldehydes.” BioEnergy Research 5, no. 2, 407-411 (2012).
  • Vanholme, R., K. Morreel, C. Darrah, J. H. Grabber, J. Ralph and W. Boerjan. “Phenolic metabolism as a natural resource for the engineering of lignin in feedstocks for biofuels and biomaterials production.” New Phytologist (2012).
  • Ress D. K. and J. Ralph. Synthesis of 3-O-vanillate and 3-O-ferulate esters of (-)-epicatechin. Journal of Agricultural and Food Chemistry, 2012, submitted 8/25/2011; updating with synthetic lignins. “
  • Grabber, J. H., D. Ress, and J. Ralph. “Identifying new lignin bioengineering targets: impact of epicatechin, quercetin glycoside, and gallate derivatives on the lignification and fermentation of maize cell walls.” Journal of agricultural and food chemistry 60, no. 20 (2012): 5152-5160.”
  • Elumalai, S., J. H. Grabber, J. Ralph and X. Pan. Incorporation of epicatechin derivatives into cell walls, and assessment of responses to pretreatment methods and subsequent enzymatic hydrolysis.BioEnergy Research, 2012, in preparation.
  • Tobimatsu, Y., S. Elumalai, J. H. Grabber, C. L. Davidson, X. Pan, and J. Ralph. “Cover Picture: Hydroxycinnamate Conjugates as Potential Monolignol Replacements: In vitro Lignification and Cell Wall Studies with Rosmarinic Acid.” ChemSusChem, 5: 4, 601, doi: 10.1002/cssc.201290013 (2012).
  • Ress, D. K., J. H. Grabber, and J. Ralph. “Lignin monomer replacement strategies: Syntheses of (-)-epicatechin ferulate, (-)-epicatechin vanillate, and 1,2-diferuloyl-(L)-tartaric Acid,” (in preparation, 2011).
  • Elumalai, S., J. H. Grabber, J. Ralph, and X. Pan. “Incorporation of epicatechin derivatives into cell walls, and assessment of responses to pretreatment methods and subsequent enzymatic hydrolysis,” (in preparation, 2011).
  • Zhu, Y. and J. Ralph. “Stereoselective synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses,” European Journal of Organic Chemistry (submitted, March 25, 2011).
  • Tobimatsu, Y., C. L. Davidson, J. H. Grabber, and J. Ralph. “Fluorescence tagged monolignols: Synthesis and application to studying in vitro lignication,” Biomacromolecules (in press, accepted, March 16, 2011).
  • Morreel, K., O. Dima, H. Kim, F. Lu, C. Niculaes, R. Vanholme, R. Dauwe, G. Goeminne, D. Inzé, E. Messens, J. Ralph, and W. Boerjan. “Mass spectrometry based sequencing of lignin oligomers,” Plant Physiology, 153, 1464-1478, doi:10.1104/pp.110.156489 (2010).
  • Vanholme, R., K. Morreel, J. Ralph, and W. Boerjan. “Lignin biosynthesis and structure.” Plant Physiology, Vol. 153, pp. 895-905, doi:10.1104/pp.110.155119 (2010).
  • van Parijs, F., K. Morreel, J. Ralph, W. Boerjan, and R. M. H. Merks. “Modeling lignin polymerization. Part 1: simulation model of dehydrogenation polymers.” Plant Physiology, Vol. 153, pp. 1332-1344, doi:10.1104/pp.110.154468 (2010).
  • Grabber, J. H., P. F. Schatz, H. Kim, F. Lu, and J. Ralph. “Identifying new lignin bioengineering targets: 1. Monolignol substitute impacts on lignin formation and cell wall fermentability.” BMC Plant Biology, 10:114, doi:10.1186/1471-2229-10-114 (2010).
  • Vanholme, R., J. Ralph, T. Akiyama, F. Lu, J. Rencoret Pazo, J. Christensen, A. Rohde, K. Morreel, R. DeRycke, H. Kim, B. Van Reusel, and W. Boerjan. “Engineering traditional monolignols out of lignins: The effects of concomitant F5H1-up-regulation and COMT-down-regulation in Arabidopsis,” (in final preparation, 2010).

Presentations

  • Zhu, Y., Y. Tobimatsu, H. Kim, C. Davidson, J. H. Grabber and J. Ralph. Identifying new lignin bioengineering targets: Hydrophilic monolignol surrogates. 243rd National Meeting of American Chemical Society, San Diego, CA, 2012
  • Tobimatsu, Y., J. H. Grabber, P. Mitra, A. Wagner, L. Donaldson, C. L. Davidson, D. Loque and J. Ralph. Fluorescence-tagged monolignols: New approaches to the study of cell wall lignification. 243rd National Meeting of American Chemical Society, San Diego, CA, 2012.
  • Elumalai, S., J. H. Grabber, J. Ralph, and X. Pan. “Evaluating the Response of Articially Lignied Maize Cell Wall Pretreatments and Hydrolysis.” 16th International Symposium on Wood, Fiber, and Pulping Chemistry, Tanjing, China, 2011.
  • Elumalai, S., J. Grabber, J. Ralph, and X. Pan. “Evaluating the Response of Artificially Lignified Maize Cell Wall to Pretreatments and Enzymatic Hydrolysis,” Proceedings of the 16th International Symposium on Wood, Fiber and Pulping Chemistry, Paper # 535, Tianjin, China, June 8-10, 2011.
  • Zhu, Y., Y. Tobimatsu, J. H. Grabber, and J. Ralph. “Potential Monolignol Replacements: Synthesis and Lignication of β-Hydroxycinnamoyl Glucosides and Monolignol γ-Glucosides,” Global Climate and Energy Project Annual Symposium, Stanford, California, 2010.
  • Tobimatsu, Y., Y. Zhu, H. Kim, F. Lu, J. H. Grabber, and J. Ralph. “Potential Monolignol Replacements: Lignication with Guaiacyl Butenol, Feruloyl Methoxytyramine, and Rosmarinic Acid,” Global Climate and Energy Project Annual Symposium, Stanford, California, 2010.
  • Ress, D. K., J. N. Rehbeck, W. Maier, H. Kim, F. Lu, J. Ralph, C. Davidson and J. H. Grabber. “Potential Monolignol Replacements: Synthetic Strategies Toward Phenolic and Diferulate Esters of Avan-3-ols, Tartaric Acid and Glucose.” Global Climate and Energy Project Annual Symposium, Stanford, California, 2010.
  • Ralph, J., X. Pan, S. Patterson, F. Lu, H. Kim, Y. Zhu, D. K. Ress, M. Opietnik, Y. Tobimatsu, T. Fabel, S. Elumali, C. Davidson, and J. H. Grabber. “Altering Lignin Biosynthesis for Improved Biomass Conversion [Efficient Biomass Conversion: Delineating the Best Lignin Monomer [substitutes]”, Global Climate and Energy Project Working Group Meeting, Stanford, California, 2010.
  • Opietnik, M., P. F. Schatz, H. Kim, C. Davidson, J. H. Grabber, and J. Ralph. “Potential Monolignol Replacements: Synthesis of Feruloyl Quinic Acids and Feruloyl Threitols.” Global Climate and Energy Project Annual Symposium, Stanford, California, 2010.
  • Grabber, J. H., J. Ralph, D. K. Ress, and X. Pan. “Incorporation of Epicatechin Esters into Lignin Enhances Cell Wall Fermentability.” 32nd Symposium on Biotechnology for Fuels and Chemicals, Hilton Clearwater Beach, Clearwater, Florida, Paper #15139, 2010.
  • Grabber, J. H., J. Ralph, and X. Pan. “Identifying New Lignin Bioengineering Targets: Monolignol Substitute Impacts on Lignin Formation and Cell Wall Utilization,” 32nd Symposium on Biotechnology for Fuels and Chemicals, Hilton Clearwater Beach, Clearwater, Florida, Paper #15069, 2010.
  • Elumalai, S., J. H. Grabber, J. Ralph, and X. Pan. “Microscale Analysis and Pretreatment Methods for Evaluating the Delignication Response of Articially Lignied Cell Walls Containing Novel Monolignols,” Global Climate and Energy Project Annual Symposium, Stanford, California, 2010.
  • Bolivar, J., T. Fabel, S. Patterson, J. H. Grabber, and J. Ralph. “In Vitro Culture Systems to Test Lignication and Cell Wall Digestibility,” Global Climate and Energy Project Annual Symposium, Stanford, California, 2010.
  • Ralph, J., H. Kim, F. Lu, D. K. Ress, Y. Tobimatsu, X. Pan, S. Patterson and J. H. Grabber. Efficient Biomass Conversion: Delineating the Best Monolignol Substitutes (introductory overview). Global Climate and Energy Project, Stanford University, California, 2010.
  • Grabber, J. H., J. Ralph, D. K. Ress and X. Pan. “Incorporation of Epicatechin Esters into Lignin Enhances Cell Wall Fermentability,” Paper #15139, 32nd Symposium on Biotechnology for Fuels and Chemicals, Hilton Clearwater Beach, Clearwater, Florida, 2010.
  • Grabber, J. H., J. Ralph and X. Pan. “Identifying New Lignin Bioengineering Targets: Monolignol Substitute Impacts on Lignin Formation and Cell Wall Utilization,” Paper #15069, 32nd Symposium on Biotechnology for Fuels and Chemicals, Hilton Clearwater Beach, Clearwater, Florida, 2010.
  • Ress, D. K., Y. Tobimatsu, H. Kim, F. Lu, J. Ralph, C. Davidson and J. H. Grabber. “Development of a Systems Based Lignification Archetype Using Unconventional Lignin Monomer Substitutes,” Global Climate & Energy Project, Stanford University, CA, 2009.
  • Ralph, J., H. Kim, F. Lu, D. K. Ress, Y. Tobimatsu, X. Pan, S. Patterson, and J. H. Grabber. “Efficient Biomass Conversion: Delineating the Best Monolignol Substitutes (introductory overview),” Global Climate & Energy Project, Stanford University, CA, 2009.
  • Ralph,J., J. H. Grabber, F. Lu, H. Kim, J. M. Marita, and R. D. Hatfield. “Incorporation of Monolignol Conjugates into Lignin for Improved Processing,” IUFRO Tree Biotechnology Conference, Whistler, BC, Canada, 2009.
  • Ralph, J. “Modification of Cell Wall Structure to Improve Biomass Processing .” Scion Seminar Series, Scion, Rotorua, New Zealand, 2009.
  • Ralph, J., J. H. Grabber, F. Lu, H. Kim, J. M. Marita, and R. D. Hatfield. “Designing Lignins for Improved Biomass Processing.” Global Climate and Energy Change (GCEP) Research Symposium, Frances C. Arrillaga Alumni Center, Stanford University, Stanford, CA, October 1-3, 2008.
  • Ralph, J., R. D. Hatfield, J. H. Grabber, F. Lu, H. Kim, and J. M. Marita. “Designing Lignins for Improved Biomass Processing.” FuncFiber International Symposium on the Biology and Biotechnology of Wood, p 14. Umeå, Sweden, March 10-12, 2008, 2008.
  • Ralph, J. “A Basis for Overcoming the ‘Lignin Problem’ in Biomass Conversion.” Contemporary Biochemistry, Biofuels Seminar Series, Ebling Symposium Center, Microbial Sciences Building, U. Wisconsin-Madison, 2008.

Updated January 2013