Chair of Chemistry of Biogenic Resources TU München - R&D activities -

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1 Chair of Chemistry of Biogenic Resources TU München - R&D activities - Chair of Chemistry of Biogenic Resources Schulgasse 18, Straubing, Germany

2 Locations Freising Niederbayern Straubing Main site >1000 m 2 Laboratory > 300 m 2 Pilot plant hall Foto: Stefan Müller-Naumann Department of Chemistry, Garching Center for catalysis Center for industrial biotechnology

3 Situation of modern chemistry Vision: Biomass substitutes mineral oil as raw material for industriall chemistry Wood, straw, vegetable oil Polymeres, dyes, surfactants, nutrients, solvents, pharmaceuticals, biofuels

4 Raw materials of industrial chemistry Crude oil is the most important raw material, but it is limited Image Source: Maurer, Henkel

5 il C2 C3 C4 C5 C6 Mineral oil refinery Distillation, Cracking, Reforming Distillation, Hydrotreating, Reforming, Cracking, Alkylation

6 Biorefinery 3 rd Generation LCB Enzyms 1 Treatment 1 Enzyme 2 Treatment 2 E3 T3 E4 T4 C5 sugars C6 sugars Proteins Lignin Low quantity substances Residual substrates Polyols & Derivatives Acetone Xylene Amino acids & Derivatives Phenols Dyes, sterins, etc. Energy recovery (combustion or fermentative utilization)

7 R&D goals 1. Development of new products based on plant biomass 2. Development of catalysts as well as processes for the conversion (Chemo- and Biotransformation) of plant biomass 3. Development of methods for HT- catalyst engineering 2 1 Plant biomass 3 3 Robotics 3 Intermediate/ Monomer 2 Biopolymer/ Material 1 2

8 Processes Catalyst development Microorganisms Metabolic Engineering Homogeneous Catalysts Synthesis of Metal complexes Enzymes Proteindesign and -evolution Heterogeneous Catalysats Surface modification Process design Yesterday Today Tomorrow A B E F G C D Fermentation A B E F C D A B E F Chemo-enzymatic Cascade reactions

9 Bioconversion of lignocellulosic biomass

10 Bioconversion of lignocellulosic biomass Lignocellulosic biomass (LCB) Enzymatic saccharification

11 Bioconversion of lignocellulosic biomass ~ 25 % ~ 20 % ~ 40 % Hemicellulose Lignin Cellulose Physico-chemical methods Pretreatment Saccharolytic / lignolytic enzymes Hydrolysates ligo- /Monsaccharides

12 Microbial polysaccharides

13 Microbial polysaccharides Strain Selection Research areas Metabolic engineering Applications Filamentous fungi Fermentation & Downstream Polyacrylat Xanthan No agent 0,02% 0,02% Bacteria Food-Pharma- Cosmetics

14 Microbial polysaccharides xanthan Polysaccharides as flocculation agent Function: - Improvement of sedimentation (e.g. in sewage sludge) Sedimentation of clay suspension Current product: - Standard is polyacrylate => not biodegradable, petro derived Essential properties: - High molecular weight - Charged Polyacrylate 0,02 % Xanthan 0,02 % No agent

15 Microbial polysaccharides - xanthan Polysaccharide produced from plant pathogen bacteria Xanthomonas campestris pv. campestris - Leaf plotch Blattfleckenkrankheit, Ölfleckenkrankheit, black rot Schwarzfäule H Cellulose chain as backbone, Mannose and glucuronic acid side H H H chains, H Mw of >10 6 Da - H Shear thinning, thixotropic H H β-d-mannose β-1,4 D-Glucose - H H H H H H H H H β-1,2 D-Mannose β-1-4-d-glucuronic acid H H at rest in movement disordered viscous ordered free flowing

16 Microbial polysaccharides low acetyl xanthan Removal of acetate Improved viscosity Increased thermostability Improved interactions with other polymers => Coproduction of acetyl esterase during xanthan production

17 Depolymerisation of lignin

18 Depolymerisation of Lignin => Combination of chemical and enzymatic methods Fraunhofer Project Group BioCat RuCl 2 (PPh 3 ) 3 ADH/GST

19 Enzymatic cleavage of Lignin s beta-aryl-ether Enzymes focused on: Lig D, Lig F and Lig G* Reference substance: Guaiacol glycerol guaiacol ether (GGE)* Tasks Expression and purification of the LigD, F, G enzyme system Determination and optimization of enzyme activities Adoption to complex lignin substrates *Sato et al., Appl Environ Microbiol 75 (16), 2009

20 Enzymatic cleavage of Lignin s beta-aryl ether LigD-, LigF- and LigG- cell extracts Synthesis of codon-optimized gene sequences (Sphingomonas spec.) by Geneart GmbH Protein overexpression in E.coli BL21 (DE3) Enzyme-assays with cell extracts and GGE cleavage of mm GGE in 150 min at 30 C, ph 8 (assay II) HPLC detection of 2 compounds GGE- concentration [mm] 0,3 0,25 0,2 0,15 0,1 0,05 0 I: 50 µl CE, II: 100 µl CE; 0.3 mm GGE reaction time [min] without enzyme Assay I Assay II Guaiacol glycerol guaiacyl ether ß-hydroxypropiovanillone guaiacol

21 Thank you for your attention!

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