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Biocatalysis and Enzyme Stability in Ionic Liquids

Outline. Ionic Liquids for BiocatalysisStructurePhysical PropertiesBiocatalytic Synthesis of AcrylatesBiocatalytic Polyester SynthesisConclusions. Hydrophilic Ionic Liquids ? Physical Properties. Hydrophobic ionic liquidsWater immiscible[BMIM][PF6]Hydrophilic ionic liquidsWater miscibleGoo

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Biocatalysis and Enzyme Stability in Ionic Liquids

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    1. Biocatalysis and Enzyme Stability in Ionic Liquids Jason Berberich, Joel Kaar, Anita Mesiano, Markus Erbeldinger, Alan Russell University of Pittsburgh McGowan Institute for Regenerative Medicine, Department of Bioengineering

    2. Outline Ionic Liquids for Biocatalysis Structure Physical Properties Biocatalytic Synthesis of Acrylates Biocatalytic Polyester Synthesis Conclusions

    3. Hydrophilic Ionic Liquids Physical Properties Hydrophobic ionic liquids Water immiscible [BMIM][PF6] Hydrophilic ionic liquids Water miscible Good solvents for very polar substrates Sugars

    4. Structures of the Ionic Liquids Used in this Study

    5. Solvatochromatic Characterization of Solvent Polarity Reichardts dye Normalized scale 0 : nonpolar solvent (tetramethylsilane) 1 : polar solvent (water)

    6. Interpretation of Biocompatibility: Octanol-Water Partition Coefficient

    7. Log P for Ionic Liquids Log P determined using the shake flask method Concentration determined using UV spectroscopy Ionic liquids have very low log P values

    8. Physical Characterization -Conclusion Solvatochromatic characterization suggests that ionic liquids have polarity similar to ethanol The very low log P values for the ionic liquids suggests that these solvents are very hydrophilic and may compete with the enzyme for water

    9. Biocatalytic Synthesis of Acrylates

    10. Effect of Solvent on Lipase Activity Lipase activity is higher in [BMIM][PF6] than in hexane No activity in polar organic solvents No activity in hydrophilic ionic liquids Lipase dissolves in some ionic liquids

    11. Can We Stabilize Lipase for use in Hydrophilic Ionic Liquids? Methods investigated to stabilize lipase for use in hydrophilic ionic liquids Lipase adsorbed on acrylic support Novozyme 435 (Candida antarctica lipase) PEG-modified lipase PEG-NCO and Candida rugosa lipase Lipase-immobilized polyurethane foam Hypol 3000 and Candida rugosa lipase

    12. Results Immobilized Lipase No activity was detected in hydrophilic ionic liquids with immobilized lipases

    13. Biocatalytic Polyester Synthesis

    14. Monomer Solubilities in [BMIM][PF6] (50C)

    15. Polymerization Studies

    16. Polyester results

    17. Stability of Novozyme 435 in [BMIM][PF6]

    18. Stability of Novozym 435 at 50C

    19. Stability of Novozym 435 at 50C in the presence of Substrates

    20. Stability of Novozym 435 at 70C

    21. Conclusions Solvatochromatic characterization and log P measurements indicate that these solvents are polar and hydrophilic. Enzymatic synthesis of 2-ethylhexylmethacrylate occurred efficiently in [BMIM][PF6] and hexane. Lipase dissolves in hydrophilic ionic liquids. Standard methods of stabilization were not affective in protecting the lipase from deactivation in hydrophilic ionic liquids.

    22. Conclusions The enzymatic polymerization of DVA and 1,4-butanediol has been achieved in [BMIM][PF6]. Enzymes of interest show enhanced stability in the [BMIM][PF6] when compared to a traditional organic solvent.

    23. Acknowledgements Sachem USA, Inc. Environmental Protection Agency (Grant R-82813101-0)

    24. Stability of Novozyme 435 in Various Ionic Liquids

    25. Stability of Novozyme 435 in Conventional Solvents

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