biosynthese von estradiol - thomas-albuzat.de filebiosynthese von estradiol 2 nadph 2 nadp+ scoa o...
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![Page 1: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/1.jpg)
Biosynthese von EstradiolOH
OH
Thomas Albuzat23. Juni 2003
![Page 2: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/2.jpg)
Biosynthese von Estradiol
Ausgangsstoff:
Acetyl-CoA ( z.B. aus Glucose-Abbau )
Acetyl-CoA Acetyl-CoA
Thiolase
(Acetyl-CoA-acetyltransferase)
Acetoacetyl-CoA
+SCoA
O
SCoA
O
O O
SCoA
H SCoA
![Page 3: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/3.jpg)
Biosynthese von Estradiol
Hydroxymethyl-CoA-synthase
(HMG-CoA-synthase)SCoA
O
O O
SCoA
H SCoA
SCoA
OOH
OO
H2O +
β-Hydroxy- β-methylglutaryl-Co-A = HMG-CoA
![Page 4: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/4.jpg)
Biosynthese von Estradiol
2 NADPH 2 NADP+
SCoA
OOH
OO
OH
OO
OH
OH
OO
O P OO
O
β-Hydroxy- β-methylglutaryl-Co-A MevalonatCoA
HMG-CoA-reduktase
ATP ADP
Mevalonatkinase
5-Phosphomevalonat
![Page 5: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/5.jpg)
Biosynthese von Estradiol
ATP ADP
OH
OO
O P OO
O
OH
OO
O P OO
OP OO
O
O P OO
OP OO
O
ATP ADP +CO2 + H2O
5-Phosphomevalonat 5-Pyrophosphomevalonat
Phosphomevalonatkinase
PyrophosphomevalonatdecarboxylaseIsopentenylpyrophosphat
![Page 6: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/6.jpg)
Biosynthese von Estradiol
+
Isopentenyl-pyrophosphat-isomerase
Isopentenylpyrophosphat Dimethylallylpyrophosphat
PP
Prenyltransferase
Geranylpyrophosphat
O P OO
OP OO
O
O P OO
OP OO
O
O P P O P P
O P P
![Page 7: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/7.jpg)
Biosynthese von Estradiol
O P P
O P P
O P P
Prenyltransferase
PPFarnesylpyrophosphat
Geranylpyrophosphat Isopentenylpyrophosphat
+
![Page 8: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/8.jpg)
Biosynthese von Estradiol
O P P OPP
NADPH NADP+ + 2 PP
Squalen-Synthase
Farnesylpyrophosphat
Farnesylpyrophosphat
Squalen
![Page 9: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/9.jpg)
Biosynthese von Estradiol
Squalen
O
NADPH + O2 NADP+ + H2O
SqualenepoxidaseSqualenepoxid
Squalen
![Page 10: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/10.jpg)
Biosynthese von Estradiol
OO
Enz HSqualenoxidocyclase
Squalenepoxid
C+
HH
HOHH
HOH
H
H
- H+
LanosterinProtosterol-Kation
![Page 11: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/11.jpg)
Biosynthese von Estradiol
HOH
H
H
Lanosterin
Demethylierung, Sättigung der Seitenkette, Wanderung der Doppelbindung im Ring B
A B
C D
Sterangerüst
OH Cholesterin
![Page 12: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/12.jpg)
Biosynthese von Estradiol
O
OHOH
Desmolase
CholesterinPregnenolon
Desmolase : Cholesterol-Side-Chain-Cleavage Enzym
![Page 13: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/13.jpg)
Biosynthese von Estradiol
O
O
Oxidation der OH-Gruppe
O
OH
Pregnenolon Progesteron
O
O
OH
Hydroxylase
17-Hydroxy-Progesteron
![Page 14: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/14.jpg)
Biosynthese von Estradiol
O
O
OH
O
O
Acetatabspaltung
Androstendion17-Hydroxy-Progesteron
O
OH
Reduktion
Testosteron
![Page 15: Biosynthese von Estradiol - thomas-albuzat.de fileBiosynthese von Estradiol 2 NADPH 2 NADP+ SCoA O HO O O HO O O OH HO O O O P O O O β-Hydroxy- β-methylglutaryl-Co-A CoA Mevalonat](https://reader030.vdocuments.net/reader030/viewer/2022040423/5e1a3fd4e8c62a71446f433d/html5/thumbnails/15.jpg)
Biosynthese von Estradiol
O
OH
OH
OH+ 4 H2O
+ HCOOH
3 NADPH + 3O2
Aromatase(Estrogensynthetase)
TestosteronEstradiol
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Biosynthese von Estradiol