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Lecture 10

Lecture 10. Cholesterol Synthesis. Bloch: Fate of Labeled CH 3 COOH. Cholesterol is made of 2 C units. Path from Acetate to Sterol. Synthesis of Mevalonic Acid. Acetoacetyl CoA. HMG-CoA synthase. (distinct from mitonchondrial). (In cytosol). Ketone Body Formation: Acetoacetate.

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Lecture 10

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  1. Lecture 10 Cholesterol Synthesis

  2. Bloch: Fate of Labeled CH3COOH Cholesterol is made of 2 C units.

  3. Path from Acetate to Sterol

  4. Synthesis of Mevalonic Acid Acetoacetyl CoA HMG-CoA synthase (distinct from mitonchondrial) (In cytosol)

  5. Ketone Body Formation: Acetoacetate

  6. Synthesis of Mevalonic Acid

  7. Synthesis of Mevalonate: HMG-CoA reductase • An integral membrane protein of the ER • Major point of regulation of cholesterol synthesis • Suppressed by uptake of LDL cholesterol

  8. Drugs that inhibit HMG-CoA reductase (Atorvastatin)

  9. CH 3 CH CH CH OH 2 2 2 CH 3 CH CH CH 2 2 2 Synthesis of Isopentenyl Pyrophosphate O C C HO OH 3 individual steps 3 ATP 3 ADP O O C C O P O HO O O O P O O P O O O

  10. CH 3 O C CH C CH CH P P O 2 2 2 O O O P O O CO 2 CH P 3 i CH C CH CH O P P Isopentenyl-PP 2 2 2 CH 3 H C C CH CH O P P Dimethylallyl-PP 3 2 Synthesis of Isopentyl Pyrophosphate Isoprenyl-PPs

  11. Isoprene Condensation: Head-to-Tail

  12. Isoprene Condensation: Head-to-Tail

  13. Isoprene Condensation: Head-to-Tail

  14. Isoprenyl Condensations Enzyme:prenyl transferase

  15. Isoprenyl Condensations Enzyme:prenyl transferase

  16. Squalene Synthesis and Ring Closure (Complicated mechanism)

  17. Squalene Synthesis and Ring Closure

  18. Squalene Synthesis and Ring Closure

  19. Squalene Synthesis and Ring Closure (19 steps) (Require NADPH and O2)

  20. Some Isoprenoids

  21. Isopentenyl-PP as Precursor

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