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In-Cell Enzymatic Glycosylation: a Way to Improve Productivity of Heterologous Biosynthesis Pathways in Micro-Organism Esben Hansen Evolva

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In-Cell Enzymatic Glycosylation: a Way to Improve Productivity of Heterologous Biosynthesis Pathways in Micro-Organism Esben Hansen Evolva Engineering Conferences International ECI Digital Archives Metabolic Engineering IX Proceedings Summer 6-7-2012 In-cell Enzymatic Glycosylation: A Way to Improve Productivity of Heterologous Biosynthesis Pathways in Micro-Organism Esben Hansen Evolva Follow this and additional works at: http://dc.engconfintl.org/metabolic_ix Part of the Biomedical Engineering and Bioengineering Commons Recommended Citation Esben Hansen, "In-cell Enzymatic Glycosylation: A Way to Improve Productivity of Heterologous Biosynthesis Pathways in Micro- Organism" in "Metabolic Engineering IX", E. Heinzle, Saarland Univ.; P. Soucaille, INSA; G. Whited, Danisco Eds, ECI Symposium Series, (2013). http://dc.engconfintl.org/metabolic_ix/19 This Conference Proceeding is brought to you for free and open access by the Proceedings at ECI Digital Archives. It has been accepted for inclusion in Metabolic Engineering IX by an authorized administrator of ECI Digital Archives. For more information, please contact [email protected]. In-cell enzymatic glycosylation A way to improve productivity of heterologous biosynthesis pathways in micro-organisms Biarritz June 7 th 2012 Disclaimer The shares of Evolva Holding (“Evolva ”) are traded on the SIX Swiss Stock Exchange (ticker: “EVE”). This presentation may contain specific forward -looking statements, relating to Evolva's future business, development and economic performance. e.g., statements including terms like "believe", "assume", "expect" or similar expressions. Such forward -looking statements are subject to known and unknown risks, uncertainties and other factors which may result in a substantial divergence between the actual results, financial situation, development or performance of Evolva and those explicitly or implicitly presumed in these statements. Against the background of these uncertainties readers should not rely on forward-looking statements. Evolva assumes no responsibility to update forward -looking statements or to adapt them to future events or developments. Evolva Confidential Material Slid Evolva Snapshot Unique, proven, widely applicable, biosynthesis technology □ Creates novel products and production methods in yeast □ More than 50 patent families filed to date Product On Addressab Family Market Market Product focus in 3 ”health & wellness” areas □ Natural flavorants and sweeteners : Vanilla, Stevia Vanilla 2014 $ 0.4 bn □ Protection against microbial pathogens : Pomecins □ Diabetes & obesity: EV -077, Stevia Pomecin 2015 $ 2 bn B2B model focused on core competencies □ Provide innovative ingredients to other companies Stevia 2015 $ 4 bn □ Partnerships with Roche, IFF, BASF, Roquette, US DoD □ 2010 revenues CHF 18.6 mn (1H 2011 CHF 6.9mn) EV-077 2017 $ 10 bn Many pharma & food majors want to grow in space □ But have limited partnering or acquisition options □ Evolva is well positioned with differentiated assets and a highly experienced team Evolva Confidential Material Slid This Presentation O Glycosylation and the effects of glycosylation HO O O O OH HO Glycosyltransferases OH Examples □ Vanillin biosynthesis in yeast □ Saffron biosynthesis in yeast □ Stevia biosynthesis in yeast Evolva Confidential Material Slid Glycosylation Glycosylation A glycoside is a molecule in which a sugar group is bonded through its anomeric carbon to another carbon group via an O-glycosidic, S-glycosidic, or N-glycosidic bond “Small molecule” glycosides play important roles in especially micro-organisms and plants, e.g. in defence Dhurrin Some toxic defence compounds are stored as non -toxic glycosides □ Cyanogenic glucoside □ E.g. dhurrin, vanillin-glucoside and glucosinolates Aglycon is unstable and degradation results in In animals, small compound glycosylation is used as a mean release of cyanide for detoxifying and excreting unwanted lipophilic compounds □ Glycosylation is performed by promiscuous glucuronosyltransferases in the liver □ Water solubility is increased, facilitating excretion via the kidneys Typical effects of glycosylating a scaffold Glucosinolate □ Decreases the compound’s cellular toxicity Hydrolyzed by myrosinases upon □ Increases the compound’s aqueous solubility tissue damage, resulting in release of biologically active □ Increases the compound’s biosynthesis rate and yield compounds □ In some cases: Stabilization of the product molecule Evolva Confidential Material Slid Glycosylation Increases Solubility of Curcumin Principal curcuminoid of the popular Indian curry spice turmeric Curcumin Increased solubility : Insoluble curcumin gains solubility by glucosylation (Kaminaga et al .) O O HO OH O O Solubility increase Glc Glc Glc Glc 22.000.000 X Glc Glc Glc 15.000.000 X Glc Glc 12.000.000 X Use : 2.300.000 X Several experimental (cancer, Glc Glc anti-inflammation, etc.) Glc 230 X et al 1 X Ref.: Kaminaga . (2003) FEBS Lett. 555: 311 Curcumin Evolva Confidential Material Slid Amplification of Microbial Production of Toxic Compounds ☺☺☺ ☺☺☺ ☺☺☺ Product glucoside Natural Natural Precursor product Precursor Product Production microorganism dies when high Production microorganism survives when concentration of toxic compound is formed toxic compound formed is glycosylated Toxic aglycon Less toxic glycoside Evolva Confidential Material Slid Glycosyltransferases “Family 1” Family 1 Glycosyltransferases – The UGTs A GT is an enzyme that can transfer a sugar from one molecule to another Family 1 UDP-glycosyltransferases (UGTs) □ 1 out of 91 GT families – a large family present in both animals, plants and microorganisms □ Small hydrophobic molecules as natural substrates □ Involved in synthesis of many different secondary plant metabolites: Pigments, defence compounds, flavour and more □ Involved in detoxification of xenobiotic compounds O O N HO N O O O N N OH O O O O O O HO O P O PO O P O PO O O + OH O O O O + O UDP-glycosyltransferase O Resveratrol UDP-glucose UDP Resveratrol-β-glucoside (Piceid) □ Use uridine diphosphate-activated sugars as sugar donors □ The catalytic mechanism is inverting, resulting in a β-configuration of the glycosidic linkage Evolva Confidential Material Slide Family 1 UGTs Most uses UDP-glucose as sugar donor Many plant UGTs have shown to be very promiscuous towards acceptor substrate Arabidopsis thaliana contains 122 different UGTs 70% of 87 small molecule drugs were glucosylated (Kristensen et al., 2008) Picture: Universität Karlsruhe Botanisches Institut Rooted phylogenetic tree – Arabidopsis thaliana UGTs Evolva Confidential Material Slide Evolva’s Glycosylation Platform Catharanthus Gram+ bacteria Drosophila Sorghum Neisseria meningitidis Bos taurus Stevia rebaudiana roseus Vanilla planifolia Crocus sativus Arabidopsis melanogaster bicolor thaliana Present platform : 220 GT enzymes Expressed in E.coli, P. pastoris, S. cerevisiae and/or in vitro Ipomoea sp. Oryza sativa Chimeric UGTs Petunia hybrida Phaseolus vulgaris Rauwolfia Citrus maxima serpentina Bellis perennis Lycopersicon esculentum Nicotiana tabacum Evolva Confidential Material Slide Possible Carbohydrate Species CH2OH CH2OH COOH CH2OH O OH HO O OH O OH O OH O OH OH OH OH OH OH HO HO HO OH OH OH OH OH NH D-Glucose D-Galactose D-Xylose D-Glucuronic acid CO CH3 N-Acetyl -glucosamine COCH3 NH OH OH O OH O CH 3 COOH OH OH OH H C OH L-Rhamnose H C OH CH2OH N-Acetyl -neuraminic acid (one type of sialic acid) Evolva Confidential Material Slide In-cell enzymatic glycosylation The Process of Making an In Cell Glycosylation for a Biosynthetic Process 1. Prerequisites: R1 OH □ Product needs to have a suitable hydroxy , thio or amino group that can be OH glycosylated R2 N □ The added sugar moiety is to some extent “wasted” – product therefore needs H2N R3 to be a high or medium priced product O Evolva Confidential Material Slide The Process of Making an In Cell Glycosylation for a Biosynthetic Process 1. Prerequisites: R1 OH □ Product needs to have a suitable hydroxy , thio or amino group that can be OH glycosylated R2 N □ The added sugar moiety is to some extent “wasted” – product therefore needs H2N R3 to be a high or medium priced product O 2. Finding a suitable glycosyltransferase that can perform the desired glycosylation Evolva Confidential Material Slide UGT Screening Assay - Finding a Suitable UGT Purified enzyme 220 UGT enzymes 170 kDa 130 kDa 95 kDa 72 kDa 56 kDa 43 kDa 34 kDa 26 kDa R1 OH OH R4 R2 N H2N R3 O Regio-specific glycosylation Substrate detected by HPLC or HPLC-MS Sugar donor Evolva Confidential Material Slide The Process of Making an In Cellell GlycosylationG for a Biosynthetic Process 1. Prerequisites: R1 OH □ Product needs to have a suitable hydroxy , thio or amino group that can be OH glycosylated R2 N □ The added sugar moiety is to some extent “wasted” – product therefore needs H2N R3 to be a high or medium priced product O 2. Finding a suitable glycosyltransferase that can perform the desired glycosylation 3. Testing the glycosylation in the desired in vivo system Evolva Confidential Material Slide Testing the glycosylation in the Desired In Vivo System 4500 Unwanted Precursor Glycoside 4000 Unwanted Side Product Glycoside 3500 Product Glycoside 3000 2500 mM μM 2000 1500 1000 500 0 UGT1 UGT2 UGT3 UGT4 UGT5 UGT6 UGT7 UGT8 UGT9 UGT10 UGT11 UGT12 An example showing varying glycosylation of heterologous pathway intermediates and end product in vivo □ Though a number of UGTs are found to do the reaction in vitro they may perform quite differently in vivo Evolva Confidential Material Slide The Process of Making an In Cell Glycosylation for a Biosynthetic Process 1.
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