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S-CoA

CO 2. O. C. S-CoA. O. C H 3. CH 2. 2NADPH + H +. C. C H 3. C H 2. C OO -. COO -. C. C. O. O. O. C. C. H 2. H 2. 2 NADP +. S-CoA. S-CoA. O. O. P. P. P. P. Hydroxymethylglutaryl-CoA. Irmelin Probst, Walter Storch Vorlesungspräsentation Biochemie Teil 1, SS 2009.

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S-CoA

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  1. CO2 O C S-CoA O CH3 CH2 2NADPH + H+ C CH3 CH2 COO- COO- C C O O O C C H2 H2 2 NADP+ S-CoA S-CoA O O P P P P Hydroxymethylglutaryl-CoA Irmelin Probst, Walter Storch Vorlesungspräsentation Biochemie Teil 1, SS 2009 Cholesterin - Synthese ADP Pi CH3 CH3 H2 HS-CoA ATP ATP Acetyl-CoA CH2 OH H3C C S-CoA HS-CoA Phospho- mevalonat- kinase Pyrophospho- mevalonat- Decarboxylase Mevalonat- kinase HMG-CoA Synthase Cytosolische Form HMG-CoA Reduktase ß-Keto- thiolase Acetyl-CoA H2 OH Abspaltung von CoA-SH HS-CoA ^ S-CoA Mevalonat = Salz der Mevalonsäure 5-Isopentenyl- pyrophosphat 5-Phosphomevalonat 5-Diphosphomevalonat Reduktion der Carboxylgruppe zur Stufe des Alkohols Acetacetyl-CoA (2 * Acetyl) HMG-CoA Isopreneinheit = aktives Isopren = Baustein aus 5 C-Atomen (C5) ADP ADP

  2. CH3 Isomerisierung CH2 C CH2 CH2 CH2 P O P H2 C P P O O P P - Abspaltung von Pyrophosphat Carbokation O P P Bildung von Squalen aus aktivem Isopren Änderung der Formeldarstellung von 5-Isopentenylpyrophosphat Prenylpyrophosphat Isopentenylpyrophosphat Prenyltransferase + Kondensation von 2 Isopreneinheiten zu C10

  3. P O P + CH2 CH2 CH2 CH2 CH2 P P P P O O O O P P P P P P O O P P - Abspaltung von Pyrophosphat Carbokation CH2 + CH2 CH2 Prenyltransferase Farnesylpyrophosphat (C15) Geranylpyrophosphat (C10) Kondensation mit einem weiteren aktiven Isopren zu C15 Kondensation von 2 Isopreneinheiten zu C10

  4. NADPH +H+ NADP+ P O P H2C Isoprenoide Vit. A Vit. E Ubichinon Kautschuk P O CH2 P P -O P P O- P Squalensynthase Farnesylpyrophosphat Squalen (C30) Kopf an Kopf – Kondensation von 2 Molekülen Farnesylpyrophosphat unter Abspaltung der beiden Pyrophosphatgruppen

  5. Squalen

  6. NADPH +H+ O2 H+ NADP+ H2O + H H CH3 H O CH3 HO H Bildung eines Epoxids H3C CH3 CH3 CH3 Squalenepoxid Squalen CH3 H3C

  7. H3C + CH3 H H CH3 CH3 H+ CH3 H CH3 HO H CH3 H3C Lanosterin

  8. Umwandlung von Lanosterin zu Cholesterin Reduktion der Doppelbindung H3C CH3 CH3 CH3 Umlagerung der Doppelbindung CH3 CH3 HO Entfernung von 3 Methylgruppen H3C CH3 HCOOH + 2 CO2 Cholesterin Lanosterin

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