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Lipases. R 1 -OH R 3 -OH native enzyme Bi-bi ping-pong mechanism !

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Presentation on theme: "Lipases. R 1 -OH R 3 -OH native enzyme Bi-bi ping-pong mechanism !"— Presentation transcript:

1 Lipases

2 R 1 -OH R 3 -OH native enzyme Bi-bi ping-pong mechanism !


4 Esterolytic vs. lipolytic activity Activity Substrate concentration Activity Substrate concentration Esterase activityLipase activity


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

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

8 Current lipase OC

9 Epoxide hydrolase from yeasts

10 Reaction mechanism of epoxide hydrolase:

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

12 Development and integration of stable aldolases in the synthesis of enantiopure functionalized nitrogen heterocycles Maud CABRIÈRES, Maurice FRANSSEN

13 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

14 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 Cyanohydrin Hydroxynitrile Lyase (HNL)

15 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

16 Aldol condensation reaction Racemic mixture!

17 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

18 Aldolase classification based on catalytic mechanism Type I Aldolase: –Donor activation –Imine intermediate Type II Aldolase: –Donor activation –Metal-dependent (Zn 2+ cofactor)

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

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

21 More information on what we do:

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