Nutritional Sweeteners and Saccharides from Renewable Feedstocks
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1 Nutritional Sweeteners and Saccharides from Renewable Feedstocks 1 David Demirjian, Ph. D. President & CEO World Congress on Industrial Biotechnology July 22,
2 2 Who is zuchem? Industrial Biotechnology Company: Process Technology Platform Carbohydrates for Human Health and Nutrition Product Focus: Nutritionals from Renewables Polyols: Mannitol, Xylitol, others Rare Monosaccharides: D-ribose, D-mannose, others Human Milk Oligosaccharides Pharma/Fine Chemicals Rare and Modified Sugar building blocks Activated sugars Glycosylated small molecules Therapeutic Oligosaccharides 2
3 Strategy 3 Polysaccharides Oligosaccharides Monomers (C5 C6 Others) Engineered enzymes and metabolism Monosaccharides Mannitol Xylitol D-mannose D-ribose L-arabinose etc (Co-substrates) Activated Sugars Oligosaccharides and Glycoconjugates Glycosylated small molecules Glycosylated proteins/aas Oligosaccharides (HMOs) 3
4 Gene/Enzyme Libraries Isomerases Oxidoreductases Sugar kinases Glycosyl Transferases Other/metabolic Glycosidases Transport Nucletoidyl Transferases Protein Stability Uptake/Export Mutants zuchem Glycochemistry Platform E. coli, Yeast, Pichia, Lactobacillus, Bacillus, others Protein Solubilization Inhibitor Tolerance Modified Sugar Metabolism Inhibitor Tolerance Strain Systems Directed Evolution Proprietary Screening Technologies Other Technology Metabolic Engineering
5 5 Sorbitol Xylitol C5 Mannitol C6 Others 5
6 Chemical Conversion Processes 6 Pure Sugar Biomass Polyol Mixture Isolated Polyol Hydrogenation Complex Recovery Expensive Inexpensive Low Yield/Specificity Expensive Feedstocks Mannitol: Fructose Xylitol: Xylose
7 zuchem Polyol Processes 7 Inexpensive Renewable Mixed Sugar Biomass Fermentation Pure Polyol Recovery Isolated Polyol Simple Safe High Yield Simple Inexpensive Feedstocks Mannitol: High Fructose Corn Syrup (Fructose + Glucose) Xylitol: Hemicellulose (Bagasse, Hardwood, Corn, etc )
8 Conversion of HFCS to Mannitol 8 Glucose 2 Fructose Lactobacillus 2 NADPH 2 NADP+ H- Lactate Acetate 2 Mannitol 8
9 (grams/l) Optimized Fed-batch Fermentation Mannitol Fructose Glucose Time(h) Feedstock: Modified HFCS (C6) Fermentation: Fed batch. Volumetric productivity 7 g/l-h and >165 g/l mannitol All fructose converted to mannitol. No other polyols Meets FCC/UPS specifications. FDA approved. Piloted to 1000L 9
10 10 Xylitol Challenges Need Abundant Feedstock Supply: Mixed C5/C6 Hemicellulose Stream Key Challenge: Little or no Arabitol produced Other: Tolerant to Feedstock Variability and Fermentation Inhibitors 10
11 Concentration (W/V) Concentration (W/V) Specific Conversion of Xylose to Xylitol XR in ara+ host Xylose Arabinose Arabitol Xylitol Conversion of Xylose to Xylitol with XI / XDH Glucose D-Xylose L-Arabinose Arabitol Xylitol Hour Hour Hours Hours 11
12 Selection of a Xylose-Specific Xylose Reductase (XR) 12 No XR NO Xylitol NO Arabitol No Growth Xylose + Arabinose Wt XR Xylitol Arabitol xdh arab Xylulose L-arabitol-5-phosphate LETHAL Mutant XR Xylitol NO Arabitol xdh Xylulose Growth XR - active on L-arabinose and D-xylose XR - D-xylose specific enzyme 12
13 Xylose Specific Mutants D-Xylose/L-Arabinose Rate Ration D-xylose/L-arabinose rate ratio Pstip XR mut#1 mut#15 mut#16 mut#17 WT MUT1 MUT2 MUT3 MUT4 13
14 Conversion of Arabinose to Xylitol 14 Xylose Xylitol Arabinose 14
15 g/l Substrate or Product Xylitol Process Optimization Xylitol Production from Hydrolysate Xylitol Feedstock: Mixed C5/C6 Hemicellulose. Fermentation: Fedbatch Xylose Glucose Hours Arabinose Arabitol Tested with dozens of feedstocks Optimized, ready for piloting 15
16 16 Human Milk Oligosaccharides (HMOs) Prebiotic and therapeutic effects Expensive/Hard to make Important HMOs not available for research or commercial applications. Scalable, economic production processes needed 16
17 17 HMO Composition >90 different HMOs detected (~5-24 g/l). Mostly derivatives of lactose. Five main building blocks: D-glucose D-galactose L-fucose N-acetylglucosamine N-acetylneuraminic acid Methods to make Activated Sugars and Oligosaccharides needed 17
18 Oligosaccharide Production Strategy 18 Kinase NT Transferase GlyT Uses proprietary engineered: Sugar-1-kinases, Nucleotidyltransferases and Glycosyltransferases (GlyT) 18
19 Making Sugar-1-Phosphates With and Engineered Kinase 19 Time 0 hr L-Rib L-Gal L-Glu L-Ara L-Xyl L-RhaL-Man L-Gul L-Fuc 6-Azi 19
20 Engineered Nucleotidyltransferase 20 Mutation introduced to increase enzyme activity toward galactose Shows activity with UTP, GTP and TTP 20
21 Initial Small Scale Oligosaccharide Testing 21 Reaction Product Structure Donor Acceptor Lacto-N-triose II GlcNAc-(β1-3)-Gal-(β1-4)-Glc UDP-GlcNAc Lactose Lacto-N-neotetraose Gal-(β1-4)-GlcNAc-(β1-3)-Gal-(β1-4)-Glc Lacto-Ntriose II LacNAc Gal-(β1-4)-GlcNAc GlcNAc Globotriose Gal-(α1-4)-Gal-(β1-4)-Glc UDP-Gal Lactose Globobiose/galabiose Gal-(α1-4)-Gal Galactose Gal-(α1-4)-Gal-(α1-6)-Glc- (α1-2)-fructofuranoside Raffinose Globotetraose GalNAc-(β1-3)-Gal-(α1-4)-Gal-(β1-4)-Glc UDP-GalNAc Globotriose 2 Fucosyllactose (2 FL) Fuc-(α1-2)-Gal-(β1-4)-Glc GDP-L-Fucose Lactose 21
22 Scale-up of UDP-Gal Activated Sugar in vitro 22 UDP-Gal UTP Galactose-1-phosphate yield after purification: 120 g/l UDP-Galactose yield 70 g/l 22
23 Production of Globotriose 23 Intermediates Required: Lactose UDP-D-galactose Reaction: Completed in 4h with a yield of 62 g/l Recent optimizations show yield of over 200 g/l 23
24 Production Status of Most Prevalent HMOs 24 Target Name R&D mg g kg ton Core Oligosaccharides LNnT LNT LNB LNH Lacto-N-neotetraose Lacto-N-tetraose Lacto-N-biose Lacto-N-hexaose Fucosylated Oligosaccharides 2 FL 3FL LNFP I LNFP II 2'-fucosyllactose 3 -fucosyllactose Lacto-N-fucopentaose I Lacto-N-fucopentaose II LNDFH I Lacto-N-difucohexaose I Sialyl-Oligosaccharides 3SL 3 -Sialyllactose 6SL 6 -Sialyllactose Feedstocks: Lactose Developed Novel Set of Engineered Enzymes Demonstrated Scale-up of several Oligosaccharides (100 grams) Expanding production of fucosylated oligosaccharides: New grant from the National Institutes of Health Currently Establishing Commercial Partnerships 24
25 Conclusion 25 Broad platform of proprietary technologies for making unusual monosaccharides and complex glycosylated molecules. Applied to a number of nutritional products now moving into commercialization. Looking to broadly apply its technology and know-how with commercial partners in a variety of product areas. 25
26 Acknowledgements 26 zuchem Enabling Carbohydrate Chemistry! Present Mike Racine, Ph.D. Leila Aminova, Ph.D. Micah Shepherd, Ph.D. Shama Khan Shreyas Patel Past Nathan Wymer, Ph.D. Pfizer Ryan Woodyer, Ph.D Tate & Lyle Paul Taylor, Ph.D. Collaborators/Consultants David Dodds, Dodds & Associates Bill Dowd, Ph.D. fmr VP R&D Dow Badal Saha, Ph.D. USDA Jürgen Rohr, Ph.D.- U. Kentucky Huimin Zhao, Ph.D. U. Illinois Yong-Su Jin, Ph.D. U. Illinois Mike Miller, Ph.D. U. Illinois Funding National Institutes of Health Biotechnology Research & Development Corp. U.S. Department of Energy National Science Foundation 26
27 27
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