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Presentation on theme: "Lipases."— Presentation transcript:

1 Lipases

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


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

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

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 research @ 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 Hydroxynitrile Lyase (HNL) Cyanohydrin

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 (Zn2+ cofactor)

19 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) Volcano Themotoga Yellowstone Sulfolobus Pacific Pyrococcus

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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