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Lipases

Lipases. native enzyme. R 3 -OH. Bi-bi ping-pong mechanism !. R 1 -OH. Esterolytic vs. lipolytic activity. Esterase activity. Lipase activity. 5. 5. 3. 3. 2. 2. Activity. Activity. 1. 1. 0. 0. 0. 2. 3. 0. 2. 3. 1. 1. Substrate concentration. Substrate concentration.

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Lipases

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  1. Lipases

  2. native enzyme R3-OH Bi-bi ping-pong mechanism ! R1-OH

  3. Esterolytic vs. lipolytic activity Esterase activity Lipase activity 5 5 3 3 2 2 Activity Activity 1 1 0 0 0 2 3 0 2 3 1 1 Substrate concentration Substrate concentration

  4. Nu dus een paar dia's....

  5. Rhizomucor miehei lipase in the closed form: nucleophilic elbow = green, lid = blue-green

  6. Candida antarctica lipase B (no lid): nucleophilic elbow = green (centre)

  7. Current lipase research @ OC

  8. Epoxide hydrolase from yeasts

  9. Reaction mechanism of epoxide hydrolase:

  10. Present research on epoxide hydrolase Resolution of: …… as chiral building blocks for pharmaceuticals More info: dr. Carel Weijers!

  11. Development and integration of stable aldolases in the synthesis of enantiopure functionalized nitrogen heterocyclesMaud CABRIÈRES, Maurice FRANSSEN

  12. IBOS PROJECT: 5 partners • IBOS: Integration of Biosynthesis and Organic Synthesis Program • Dr. Franssen/Prof. Sudhölter (Org. Chem. WU) • Dr. van der Oost/Prof. de Vos (Microbiology WU) • Prof. Kieboom, University of Leiden (Bio-org. Chem. UL) • Prof. Rutjes, University of Nijmegen (Org. Chem. KUN) • Industrial partner: DSM

  13. General framework of IBOS project • Schematic overview of the project: • Final goal: integration of new generation of Aldolases in a cascade of biocatalytic conversions, aiming at the synthesis of novel nitrogen heterocyclic compounds: Aldehyde Hydroxynitrile Lyase (HNL) Cyanohydrin

  14. C-C bond formation relevance “ Carbon- carbon bond formation lies at the heart of many organic synthesis ” Today’s fine chemistry challenge: forming building blocks with complete control of the stereochemistry of stereogenic centres Aldol reaction: one of the most powerful and famous method to enlarge carbon skeleton

  15. Aldol condensation reaction • Racemic mixture!

  16. Aldol condensation: Nature uses aldolases • Specific group of lyases, very stereoselective • Nearly 30 natural aldolases identified (2000) • Broad range of acceptors • Stringent requirement for donors

  17. Type I Aldolase: Donor activation Imine intermediate Type II Aldolase: Donor activation Metal-dependent (Zn2+ cofactor) Aldolase classification based on catalytic mechanism

  18. Volcano • Themotoga • Pacific • Pyrococcus • Yellowstone • Sulfolobus Aldolases from (hyper)thermophilic microorganisms • Archaea and bacteria with Toptimum > 80 ° C • Deep sea smokers: Pyrococcus • Shallow marine vents: Thermotoga (DHPS) • Acidic hot spring: Sulfolobus (KDG)

  19. Relevant Aldolases involved in this project • KDG (2-keto-3-deoxy gluconate aldolase): • DHPS (2,3-dihydrodipicolinate synthase): • DERA (2-deoxyribose-5-phosphate aldolase):

  20. More information on what we do: http://www.ftns.wau.nl/oc/research/biocatalysis/biocatalysis.htm

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