![Page 1: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/1.jpg)
H. Scheer
Phytochemie P. Braun / H. Scheer
WS 2007 / 2008
![Page 2: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/2.jpg)
H. Scheer
Inhalte Vorlesung Donnerstags 11:30 – 13:00, Kl. Hörsaal Botanik
Pflanzentypische StoffwechselwegeTetrapyrrole, Isoprenoide, Flavonoide Acetogenine, AlkaloideLipide
Prinzipien der Isolierung und Strukturaufklärung
Abschlussklausur Donnerstag, 7.2.08 11:30
Fragen zur VorlesungZugangsberechtigung zum Praktikum
Praktikum 10. – 15.3.08, ganztägig, Vorbesprechung 7.2.2008, 12:30, Kl. Hörsaal
Isolierung von PflanzeninhaltsstoffenSelbständiges Arbeiten nach Vorschrift (Anleitung, Bücher)Seminare jeweils Freitags
![Page 3: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/3.jpg)
H. Scheer
Lehrbücher zur Phytochemie
Klassische Biochemie Lehrbücher (Stryer, Voeth & Voeth, Lehninger)
Heldt: Pflanzenbiochemie, Spektrum Verlag (2003)
Richter: Biochemie der Pflanzen, Thieme, Stuttgart (2002)
Buchanan, Gruissem & Jones (2000). Biochemistry and Molecular Biology of Plants. Amer. Soc. Plant Physiol. Rockville, Md.
![Page 4: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/4.jpg)
H. Scheer
Wichtige Stoffklassen
Tetrapyrrole 150
Isoprenoide >22.000TerpeneCarotinoideSteroleGibberellinePolyprenoide
Phenylpropanoide >5.000FlavonoideStilbenoideMonolignole
Alkaloide >10.000
![Page 5: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/5.jpg)
H. Scheer
http://www.expasy.ch/cgi-bin/search-biochem-index
![Page 6: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/6.jpg)
H. Scheer
Anaplerotic reactions
![Page 7: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/7.jpg)
H. Scheer
Aminosäure Biosynthesen - ÜbersichtH-C=O
COOH
C=O
COOH
CH3
C=O
COOH
CH2
COOH
C=O
COOH
CH2
CH2
COOH
H2-C-NH2
COOH
H-C-NH2
COOH
CH3
H-C-NH2
COOH
CH2
COOH
H-C-NH2
COOH
CH2
CH2
COOH
Ser, Cys, Trp
Val, Leu
Asn, Lys, Homocystein, Met, Thr, Ile
Gln, Pro, Ornithin, Arg, Lys
Phe, Tyr, Trp+ Ery-4-P PRPP
His
Glyoxylat
Pyruvat
Oxalacetat
Ketoglutarat
Gly
Ala
Asp
Glu
, Tetrapyrrole
![Page 8: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/8.jpg)
H. Scheer
Tetrapyrrole -Strukturen-Cyclische Tetrapyrrole
-Lineare Tetrapyrrole
-Funktionen-Fe – Tetrapyrrole -Redoxreaktionen
-O2 –Transport
-Oxigenierungen
-Mg – Tetrapyrrole -Lichtsammlung
-Energietransduktion-Redoxreaktionen
-Co – Tetrapyrrole - C – Gerüstumlagerungen
-Methylierungen
-Ni – Tetrapyrrole - Methan-Bildung
-Biosynthese - -Aminolävulinsäure
- Protoporphyrin IX- Modifikationen und Metallierungen- Ringöffnung
-Abbau - Ringöffnung
- Folgereaktionen
-Spektroskopie
![Page 9: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/9.jpg)
H. Scheer
HO H
N N
NN
Fe
O
H
COO-COO-
Häm(Cytochrom a)
N N
NN
Fe
COO-COO-
N N
NN
Fe
COO-COO-
Häm A(Cytochrom b)
Häm-bis-Thioether(Cytochrom c, f)
S
Cys (Apoprotein)
S Cys (Apoprotein)
Häm-Typen: I
Endoxidase Atmungskette
Hämoglobin PeroxidasenCytochrom P450
Cytochrom c Cytochrom f
![Page 10: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/10.jpg)
H. Scheer
N N
NN
Fe
HOOC
COO-COO-
Siro-Häm
N N
NN
Fe
COO-COO-
Häm D
COOH
HOOC
COOH
COOH
COOHHOOCOH
OH
Häm-Typen: II
Sulfit – Reduktase Nitrit – Reduktase(6 e- - Reduktion zu NH3)
Nitrit – Reduktase(1 e- - Reduktion zu NO)
![Page 11: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/11.jpg)
H. Scheer
Chlorophylle vom Porphyrin – Typ (Chl c)
R1
R2
Mg
O
N N
N N
COOCH3
H
COOR3
Mg
O
N N
N N
COOCH3
H
OO
OO
O
O
O
O
HO
OH
OH
Pigment R1 R2 Remarks
Chl(ide) c1 CH3 C2H5 1Chl(ide) c2 CH3 C2H3 1Chl(ide) c3 COOCH3 C2H3/5 1,4PChl(ide) a CH3 C2H5 2[8-Vinyl]-PChl(ide) a CH3 C2H3 1,2,3
![Page 12: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/12.jpg)
H. Scheer
Absorptionsspektren der Chlorophylle
![Page 13: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/13.jpg)
H. Scheer
Chlorophyllevom Chlorin – Typ: Oxygene Photosynthese
R1 R2
R3
Mg
O
N N
N N
H
H
R5
R4
COOR 6
1
2
3
4
5
6
7
8
9
10
11
13
131132
1415
1617
18
19
20
21 22
2324
A B
CD
E
Phytyl =
Pigment R1 R2 R3 R4 R5
Chl a C2H3 CH3 C2H5 H COOCH3
R6
PhyChl a' C2H3 CH3 C2H5 COOCH3 H PhyChlid a C2H3 CH3 C2H5 H COOCH3 HChl b C2H3 CHO C2H5 H COOCH3 PhyChl d CHO CH3 C2H5 H COOCH3 Phy[8-Vinyl]-Chl a C2H3 CH3 C2H3 H COOCH3 Phy82-OH-Chl a C2H3 CH3 C2H4-OH H COOCH3 PhyPhe a C2H3 CH3 C2H5 H COOCH3 Phy
![Page 14: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/14.jpg)
H. Scheer
Chlorophyllevom Chlorin – Typ: Anoxygene Photosynthese(Grüne Bakterien)
R1
R2
R3
Mg
O
N N
N N
H
H
COOR4
OH
R5
*
Pigment R1 R2 R4
BChl c CH3 et,pr,ib,np Farn,18:0,many others
R5
CH3
BChl d CH3 HBChl e CHO CH3
et,pr,ib,np
et,pr,ib,np
Farn,18:0,many others
Farn,18:0,many others
R3
me,et
me,et
me,et
![Page 15: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/15.jpg)
H. Scheer
Chlorophylle vom Bakteriochlorin – Typ:
Anoxygene Photosynthese
R1
M
O
N N
N N
H
H
COOCH3
H
COOR4
H
R3
R2
Pigment R1 R2 R4
BChl a COCH3 H variableBChl b COCH3
BChl g C2H3
=CH-CH3
=CH-CH3
variable
variable
R3
CH3
As a rule, M = Mg, in Acidiphilium rubrum M = Zn
![Page 16: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/16.jpg)
H. Scheer
Andere Metallo – Tetrapyrrole
Methyl-CoM - Reduktase Methyltransferasen, Isomerasen(z.B. Methyl-Malonyl-CoA Succinyl-CoA)
O
N
N
HO
OH
N N
NN
Ni
HOOC
COOH
CO
Cobalamin (Vitamin B12)
CO
Ni-F430
ONH
H2NOC
HOOC
N
O
COOH
COOH
H2NOC
CONH2
H
H
H
+
R+
H
(R = 5'-desoxyadenosyl)
PO2
O
N
N
CONH2
H2NOC CONH2
H2NOC
N
N
Co
![Page 17: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/17.jpg)
H. Scheer
Andere cyclische Tetrapyrrole I
O
O
N HN
NH N
O
OH
O
CH3COO
HO
OCOCH3
H
H
Tolyporphine
Cyanobakterien (Tolypothrix)(Schutzpigmente ?)
Zn
O
N N
N N
H
H
COOCH3
H
COOR
O
H
H
Zn-BChl a
Purpurbakterien (Acidiphilium) Photosynthese
![Page 18: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/18.jpg)
H. Scheer
Andere cyclische Tetrapyrrole II
• Tunichlorine: Ni – Chlorine, wahr- scheinlich Schutzpigmente
(Tunicaten)
• Bonnelin: Pyropheophorbid – Derivat, geschlechtsbetimmend
(Bonella viridis, mariner Wurm)
• Namenlos: Pyropheophorbid – Derivat, Sehpigment in Tiefseefisch Melanocosteus niger
![Page 19: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/19.jpg)
H. Scheer
Lineare Tetrapyrrole
NH
NH N
COOH
COOH
HN
O O
H
NH
NH N
COOH
COOH
HN
O O
H
NH
NH N
COOH
COOH
HN
O O
Phycicyanobilin (PCB) Phycoerythrobilin (PEB)
Phycoviolobilin (PVB)
1617
1819 1
2
3
4
5
67
89
1011
1213
14
15
31
32
H
H
NH
NH N
COOH
COOH
HN
O O
Phycourobilin (PUB)
H H
Type 1 chromophores: 3-ethylidene group
Type 2 chromophores (some hypothetical): 3-vinyl group
NH
NH N
COOH
COOH
HN
O O
H
Phytochromobilin (PB)
NH
NH N
COOH
COOH
HN
O O
Biliverdin (BV)
![Page 20: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/20.jpg)
H. Scheer
Protoporphyrin IX
NH HN
NH HN
COOHCOOH
Protoporphyrinogen IX
NH HN
NH HN
COOHCOOH
Uroporphyrinogen III
HOOC
HOOC
COOH
COOH
COOH
COOH
NH HN
NH HN
COOH
HOOC
Hydroxymethyl-Bilan
HOOC
COOH
COOH
COOH
COOH
HOOC
NH
HOOC
COOH
NH2
NH2
COOH
O
COOH
COOH
NH2
COOH
NH2
COOH
COOH
+
GlycinSuccinic acid
Glutamic acid
5-Aminolevulinic acidPorphobilinogen
C5-Pathway
C4+1-Pathway
2x, - 2H2O
- 3 NH3
Cyclization, ring rotation, - H2O - 6 CO2 Oxidation
(1)
(2)
(3)
(4)
(5) (6) (7)
Siroheme, F430, Vitamin B12 Chlorophylls
4x
Hemes
MgFe
HO
Bilins
- Fe - Mg
CO
NH N
N HN
COOHCOOH
1
2
3
45
6
7
8
9
10
11
12
1314
1516
17
18
19
20
A B
CD
Biosynthese der Tetrapyrrole - Übersicht
![Page 21: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/21.jpg)
H. Scheer
a) b)
glutamyl-tRNA
NADPH NADP+
COOH
H2N
O
O
N
NN
N
NH2
O
OH
CH2
tRNA
tRNAGlu
GluTR
GSA
COOH
H2N
OH
ALA
COOH
H2NH
O
GSAM
PLP/PMP
glutamycin
COOH
H2N
O
OH
N
NN
N
O
N
CH2
OH
N
C5-Weg der ALA - Synthese
(aus Jahn, 2003)
![Page 22: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/22.jpg)
H. Scheer
a b
1
1
22
3
4
53
s
tRNAGlu tRNAGlu
as as
acac
acsacs
d
d g
n
GluRS GluTR
as: Aminosäure-Bindungsstelleac: Anticodonacs: Anticodon Stamm
g Glutamycinn: NADPH-Bindungsstelles: Rückgrat Helix
Komplex der tRNAGlu mit:
(aus Jahn, 2003)
Glu-tRNA-Synthetase (GluRS) Glu-tRNA-Reduktase (GluTR)
![Page 23: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/23.jpg)
H. Scheer
a
b
Jahn et al, Fig. 4: Glu-tRNA-Reduktase aus Methanopyrus kandleri
1
1
1
1
2
2 2
2
3
3
3 3
g
g
gg
n
n
n
n
s
s
ss
g: Glutamycinn: NADPHs: Rückgrat Helix
Glu-tRNA-Reduktase aus Methanopyrus kandleri
(aus Jahn, 2003)
![Page 24: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/24.jpg)
H. Scheer
a
b
tRNAGlu
tRNAGlu
tRNAGlu
GluTRGluTR
GluTR
GluTR
GSAM
GSAM
GSAMALA-Synthese (C5-Weg):Modell für Substrate Channeling
Glu-Semialdehyd-2,1-Aminomutase(grau/weiss)
Glu-tRNA-Reduktase(grün/gelb)
Glu-tRNA (blau)
(aus Jahn, 2003)
ALA C5-Weg:Modell für Substrate Channeling
![Page 25: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/25.jpg)
H. Scheer
5-Aminolevulinsäure und Porphobilinogen
HN
COOH
COOH
NH2
NH2
COOH
O
COOH
COOH
H2N
COOH
NH2
COOH
COOH
+
Glycine Succinate
Glutamate
5-Aminolevulinate (ALA) Porphobilinogen (PBG)
5-AminolevulinateDehydratase
2 x ALA, - 2 H2O
C5 - Pathway
C4 + C1 - Pathway
![Page 26: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/26.jpg)
H. Scheer
Von Porphobilinogen zum Corpoporphyrinogen III
NH HN
HN
HN
COOHCOOH
Uroporphyrinogen IIIHOOC
HOOC
COOH
COOH
COOH
COOH
NH HN
NH HN
COOH
HOOC
Hydroxymethylbilane I
HOOC
COOH
COOH
COOH
COOH
HOOC
Uroporphyrinogen III Synthase Uroporphyrinogen III
Siroheme, F430, Vitamin B12
HO
Enzyme-bound hexapyrrole intermediate
NH HN
NH HN
NH HN
Enzyme-CysHydroxymethylbilane I
NH HN
NH HN
COOHCOOH
HOOC
HOOC
COOH
COOH
COOH
COOH
Spiro-intermediate
COOH
COOH
COOH
COOH
COOH
COOH
COOH
COOH
HOOC
HOOC
COOH
COOH
Hemes, Chls, BChls
Decarboxylase
Hydroxymethylbilane I Synthase
A B
CD
A B
CDSynthase
4 x PBG, - 4 NH3
+
![Page 27: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/27.jpg)
H. Scheer
13C – Markierung Chl a
5
15
10
20
14 16 4 9
![Page 28: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/28.jpg)
H. Scheer
13C–13C – Kopplungen in Chl a
C-14 C-16C-4
C-9
C-10
C-15
C-5
C-20
[ppm]
COO-
CH2
CH2
C=O
CH2
NH2
Chl a
![Page 29: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/29.jpg)
H. Scheer
Vom Coproporphyrinogen III zum Protoporphyrin IX
Uroporphyrinogen III
Uroporphyrinogen III
NH HN
NH HN
COOHCOOH
HOOC
HOOC
COOH
COOH
COOH
COOH
Decarboxylase
NH HN
NH HN
COOHCOOH
COOH
COOH
- 4 CO2
Coproporphyrinogen III
Protoporphyrinogen IX
Protoporphyrinogen IX
NH HN
NH HN
COOHCOOH
Oxidase
NH N
N HN
COOHCOOH
Protoporphyrin IX
Coproporphyrinogen IIIOxidase
- 4 CO2, - 2 H2O+ O2 - 3 H2O+1.5 O2
![Page 30: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/30.jpg)
H. Scheer
F. Meyer-Betz : Ein Selbstversuch (1912)
Schwellungen nach intravenöser Injektion von 0,2 Gramm Hämatoporphyrin(einem Verwandten des Chlorophylls und des Blutfarbstoffs) und anschließendem
Aussetzen ans Sonnenlicht. Dr. Meyer-Betz, der diesen Selbstversuch am 14.10.1912 durchgeführt hatte, war noch Anfang Dezember Lichtempfindlich, erst im Frühjahr
1913 war er wieder völlig desensibilisiert. H. Scheer, 9/05
![Page 31: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/31.jpg)
H. Scheer
Porphyrie: Die königliche Krankheit
König Georg III von England und König Friedrich Wilhelm I von Peußen litten unter Porphyrie, bei der der Stoffwechsel des Blutfarbstoffs gestört ist. Durch die
angehäuften Porphyrine werden die Patienten lichtempfindlich, sie führt außerdem zu schweren Störungen im Gehirn. Ihre Krankheit war genetisch bedingt und lässt sich
über mehrere Generationen verfolgen.
Auch bei Graf Dracula wird eine Porphyrie als Ursache der Lichtscheu und des Blutbedarfs vermutet
Georg III (1738 – 1820)
H. Scheer, 9/05
![Page 32: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/32.jpg)
H. Scheer
Porphyrie: Ursachen
Der Münchener Porphyriker Petri hat jahrelang seinen rotweinfarbenen Urin (rechts im Glas) der Arbeitsgruppe von Prof. Hans Fischer zur Verfügung gestellt, und damit
zur Strukturaufklärung des Blutfarbstoffs beigetragen. H. Scheer, 9/05
Porphyrien können genetisch bedingt sein, oder durch Umwelteinflüsse hervor gerufen (z.B. Schwermetalle). Sie können auch dadurch verstärkt werden. So nimmt man an, dass die Krankheit bei Georg III besonders schwer war, weil er mit (Arsen-haltigem) Antimon behandelt wurde.
![Page 33: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/33.jpg)
H. Scheer
Vom Protoporphyrin IX zu Proto-Häm und Chlorophyll a
NH N
N HN
COOHCOOH
Protoporphyrin IX
Mg-Chelatase
N N
N N
COOHCOOH
Mg-Protoporphyrin IX
ADP, PiMg++, ATP
8-Vinyl-Reductase
N N
N N
COOCH3COOH
Protochlorophyllide a
NADPNADPH
SAM:Mg-Protoporphyrin IXMethyltransferase
N N
N N
COOCH3COOH
Mg-Protoporphyrin IX Monomethylester
SAM
H
Mg Mg
Mg
N N
N N
COOCH3COOH H
Mg
Mg-Protoporphyrin IX
NADP/H2O
Monomethylester Cyclase
NADPH
and/orO2
and/or
H2O
[8-Vinyl]-Protochlorophyllide a
N N
N N
COOHCOOH
Fe-Protoporphyrin IX
Fe
Fe-Chelatase
(Protoheme)
SAH
O O
![Page 34: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/34.jpg)
H. Scheer
Chlide c2 + other c-type chlorophyll(ide)s
a) Mg-insertion (9) Dehydrogenation
Protoporphyrin IX
NH N
N HN
COOHCOOH
1
2
34
56
7
8
9
10
11
12
1314
1516
17
18
19
20
A B
CD
Mg-Protoporphyrin IX-133-mme
N N
N N
COOCH3COOH
N N
N N
COOCH3COOH
b) Methylation by SAM (10)
H
Mg
N N
N N
COOCH3COOHH
Mg
OO
N N
N N
COOCH3COORH
Mg
O
N N
N N
COOCH3COORH
Mg
O
N N
N N
O
COOCH3COORH
Mg
O
N N
N N
COOCH3COOHH
Mg
O
Chl a (+ BChl g?) Chl b[3-Hydroxyethyl]-Chlide a
BChl a (+ b, g ?)
N N
N N
R
R
HCOORH
Mg
O
BChls c, d, e
a) Hydrogenation ring D (12, 13)
b) Esterification (GGPP, Fig.8) (15) Hydrogenation of alcohol (16)
Oxygenation (17)
Reduction (18)
HO
a) Hydrogenation ring B (13a)
b) Esterification (GGPP, Fig.8) (14) Hydrogenation of alcohol (16)
Hydrogenation ring D (13)
HO
RSeveral reactions
?
MgCyclization (11)
+ other modifications
PChlide a
Hydratation 3-vinyl group
OH
Hydrogenation 8-vinyl (14)Hydrogenation 8-vinyl (14)
H
H HH
H
H
HHH
H
H
H
H
(8)
Porphyrine(ungesättigt)
Chlorine(Dihydro)
Bacteriochlorine(Tetrahydro)
Die verschiedenen Chlorophylle
![Page 35: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/35.jpg)
H. Scheer
Absorptionsspektren der Chlorophylle
![Page 36: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/36.jpg)
H. Scheer
Vom Häm zu den Gallenfarbstoffen und Biliproteinen
NH
NH N
COOH
COOH
HN
O O
H
3E-PCB
15,16-Dihydrobiliverdin
NH
NH N
COOH
COOH
HN
O O
Biliverdin
NH
NH N
COOH
COOH
HN
O O
H
Heme
PC, PEC, APC, Phytochromes
Heme-Oxygenase Biliverdin-15,16-hydrogenase
Fd
Apoproteins
3E-PB
Fe
Ancient Phytochromes
Apoproteins
CO
PCB-OxidoreductasePcyA
PEB-Oxidoreductase
Phycobilin-LyasenCpcE, F, S,T,U,V
Heme-OxigenaseCO
![Page 37: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/37.jpg)
H. Scheer
Photosynthetische Einheit
![Page 38: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/38.jpg)
H. Scheer
Phytochrom
![Page 39: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/39.jpg)
H. Scheer
Insektenbiline
![Page 40: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/40.jpg)
H. Scheer
Conformation and charge control absorption
![Page 41: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/41.jpg)
H. Scheer
Phycobiline: Nativ
NN N
COO-COO-
N O
SCys
H
H
H
84-
O
H
NN N
COO-COO-
N O
SCys
H
H
H
A
BC
DO
H
H
Phycocyanobilin - adduct
31-Cys - phycoviolobilin
NN N
COO-COO-
N O
SCys
H
H
H
O
H
31(,181-Di)-Cys - phycoerythrobilin
H H HH
H
S
Cys
HN N
COO-COO-
N O
SCys
H
H
H
84-
O
H
31(,181-Di)-Cys - phycourobilin
HH
S
Cys
![Page 42: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/42.jpg)
H. Scheer
N
NH
N
HNCOOH
COOH
O
O
Non-fluorescent
N
NH
NH
HNCOOH
COOH
O
O
Fluorescent
![Page 43: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/43.jpg)
H. Scheer
nativ denatured renatured boarder
Conformational mobility controls fluorescence
Phycocyanin fluorescence
![Page 44: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/44.jpg)
H. Scheer
IQPHGV
Spontaneous chromophore addition to PhyA from Anabaena PCC7120
![Page 45: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/45.jpg)
H. Scheer
Chromophore ligation
Autocatalytic Catalytic
E/F-type lyaseS/U/V lyasesT-lyase
84: faulty bindingß84: faulty bindingß155: unclear
![Page 46: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/46.jpg)
H. Scheer
E/F – Type Lyases
HN
O
HNHN+ RSH
HN
OH
HN
S
R
H
HN
O
HN+ RSH
H
HN
O H
HN
S
R
Isomerization
(C)
(B)
(A)
(D)COO
- COO-
COO-
COO-
1
2
5 = PCB
6 = PVB
H
H H
Lyase-only type
PCB:-CPC - Lyase
(Cys-a84 specific)
Isomerising lyase PVB:a-PEC - Lyase
![Page 47: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/47.jpg)
H. Scheer
Isoprenoide: Übersicht
O
PP
O
PP
O
PP
+ O
PP
TerpeneOH HO
HO
O
PP
O
PP
Sesquiterpene
Diterpene
SqualenSteroide
HO OH
COOHCHO
Carotinoide
OH
OH
O
CH3COO
OO
C
Dolicholphosphat
Kautschuk, Guttapercha
2 x
2 x
+ C5
+ C5
+ 5 x C5
+ n x C5
O
PP
+ n x C5
O
P
Prenyl-Chinone
3 Acetyl-CoA
GAP + Pyruvat O
OH
OH
P
HOOC
OH
O
PP
Übersicht Isoprenoide mit Beispiel-Strukturen der Endprodukte
Mevalonat - Weg (Tiere, Cytoplasma bei Pflanzen)
Deoxyxylulose - Weg (Plastiden, Bakterien)
Chlorophylle (Alkohol an C-173)
Isoprenoide.cdr (H. Scheer)
Beispielstrukturen
Beispielstrukturen
Beispielstrukturen
Beispielstrukturen
Geranyl-pyrophosphat
Farnesyl-pyrophosphat
Geranyl-gerany-pyrophosphat
![Page 48: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/48.jpg)
H. Scheer
Isoprenoide höherer Pflanzen
Aus Heldt, Pflanzenbiochemie; Spektrum Verlag
![Page 49: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/49.jpg)
H. Scheer
Dolicholphosphat(aus Stryer, Biochemistry, 2002)
Cytoplasma
ER-Lumen
![Page 50: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/50.jpg)
H. Scheer
Carotinoide: Endgruppen
![Page 51: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/51.jpg)
H. Scheer
Einige Carotinoide
![Page 52: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/52.jpg)
H. Scheer
Carotinoide: Spektroskopie II
![Page 53: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/53.jpg)
H. Scheer
Carotinoide: Spektroskopie I
![Page 54: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/54.jpg)
H. Scheer
Carotinoide: Spektroskopie III
![Page 55: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/55.jpg)
H. Scheer
O
S-CoA
2 xO
S-CoA
O O
S-CoA
OH
COOH
OH
OH
COOH
O-PP
OH
COOH
O-PP
Acetyl-CoA
2 NADPH
CoA-SHCoA-SH
2 ATP
2 ADP+ 2 NADP
Acetoacetyl-CoA 3-Hydroxy-3-methyl-glutaryl-CoA Mevalonat Mevalonyl-pyrophosphat
Isopentenyl-pyrophosphat
Mevalonat - Weg
O
COOH P-O
OH
CHO
+
CH3
O
HO
OH
CH2O-P
CH2OH
H3C
OH
CH2O-P
CH2OH
H3C
OH
CH2O-CDP
OH O-P
CH2OH
H3C
OH
O
O P
O
P
Deoxy-xylulose - Weg
TPP
CTP, ATP
PPi, ADP CMPCO2
Acetyl-CoA-Transferase HMG-CoA-Synthase HMG-CoA-ReduktaseMevalonat-KinaseP-Mevalonat-Kinase
Diphosphomevalonat -Decarboxylase
Deoxyxylulose-5-P-Synthetase Dox-5-P-Reduktase-Isomerase Synthase Cyclase
NADPH
NADP
Pflanzen: Cytosol(Wirbel)tiere
Pflanzen: PlastideCyanobakterienEubakterien (E. coli, B. subtilis)Streptomyces
Streptomyces
Protozoen, Plasmodium
Pyruvat GAP 1-Deoxyxylulose-5-P 2-Methyl-erythritol-4-P CDP-MEP cyclo-MEPP
Alternative Wege zum IPP
Fe4S4
![Page 56: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/56.jpg)
H. Scheer
Inhibitor des Mevalonat - Wegs
O
S-CoA
OH
COOH
OH
OH
COOH
2 NADPH
CoA-SH+ 2 NADP
3-Hydroxy-3-methyl-glutaryl-CoA Mevalonat
HMG-CoA-ReduktaseHO
COOH
OH
Mevinolin (aus Aspergillus terreus)
![Page 57: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/57.jpg)
H. Scheer
Mevalonat- und Deoxyxylulose-Weg: Markierungen aus Glucose
Aus Eisenreich et al., 2004
GAP
GAP
Pyr
Pyr
Acetyl-CoA
Acetyl-CoA
Mevalonat - Weg
Deoxyxylulose- Weg
![Page 58: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/58.jpg)
H. Scheer
Abschätzung von Markierungsraten aus 1-13C-Glc
Aus Eisenreich et al., 2004
Leu-C2 stammt aus Acetyl-CoA
Tyr-C3 stammt aus Pyruvat und GAP
Val-C4 stammt aus Hydroxyethyl-TPP (= Pyruvat)
![Page 59: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/59.jpg)
H. ScheerAus Eisenreich et al., 2004
Markierungsvergleich
![Page 60: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/60.jpg)
H. ScheerAus Eisenreich et al., 2004
Produkte des Deoxyxylulose-Wegs (1)
![Page 61: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/61.jpg)
H. ScheerAus Eisenreich et al., 2004
Produkte des Deoxyxylulose-Wegs (2)
![Page 62: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/62.jpg)
H. Scheer
Phylogenie der Isoprenoid-BiosynthesewegeDeoxy-Xylulose-Weg Mevalonat-Weg
Archaea +
Bakterien Aquifales +Chlamydien +Cyanobakterien +B. subtilis +Deinococcus +Staphylococcus +Streptomyces +E. coli +Borrelia +Listeria + +
Tiere +
Pflanzen + (Plastid) +
Hefen +
Protozoen Plasmodium +
![Page 63: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/63.jpg)
H. Scheer
NADPH NADP
Fosmidomycin FR 900098
Inhibitoren
2C-Methyl-D-erythritol-4-phosphat-synthaseals Antimalaria-Target
![Page 64: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/64.jpg)
H. ScheerAus Eisenreich et al., 2004
Analyse von Gerüstumlagerungen
![Page 65: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/65.jpg)
H. Scheer
OPP
OPPH H
OPP
Kopf-Schwanz-Kondensation
Kettenverlängerung
![Page 66: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/66.jpg)
H. Scheer
Symmetrische Kondensation
ROPP
Kopf-Kopf-KondensationR
OPP
R
OPP
R
HPPi
R
R
PPi-
R
R
PPi
RR
R = C5: Squalen
R = C10: Phytoen
H- (NADPH)
+
![Page 67: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/67.jpg)
H. Scheer
Squalenepoxid-Mutase
Squalen-2,3-Epoxid Lanosterin
![Page 68: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/68.jpg)
H. Scheer
2 x
2 x
Diapophytoene synthase
Phytoene synthaseOPP
OPP
HO
OH
O
O
OH
H3CO
O
CH3O
OCH3
O
O
GlcRO
O
OGlc
OR
O
CH3O
CHO
HO
HO
OH
IPP
DMAPP2 x IPP
Diapophytoene
C30 - Carotenoids Phytoene
Neurosporene
Lycopene
Green Plants
-Carotene
Violaxanthin
Lutein
13-cis-Rhodopinal
Spheroidenone
SpirilloxanthinOkenone
Isoreniaretene
Heliobacteria
Rhodospirillaceae
Rhodospirillaceae
Thiocapsa(Chromatiaceae)
ChlorobiaceaeChloroflexaceae
Phytoene desaturase
ChromatiaceaeRhodospirillaceae
Aerobics
ChromatiaceaeRhodospirillaceae
Aerobics
Aerobics
Chromatiaceae
Ectothiorhodospiraceae
Chloroflexaceae
ChloroflexaceaeGreen plantsGreen plants
Diaponeurosporene
Aerobics
AerobicsAlgae
Algae
Algae
OH
OH
O
CH3COO
OO
C
Peridinin
Farnesyl-pyrophosphate
Geranylgeranyl-pyrophosphate
Algae
-cyclase
Green plantsAlgae
-cyclase
-cyclase
Cyanobacteria
Cyanobacteria
Prochlorophytes
Prochlorophytes
-Carotene
Carotinoide
![Page 69: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/69.jpg)
H. Scheer
![Page 70: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/70.jpg)
H. Scheer
Shikimatweg
Pflanzen Pflanzen
CH2OP
OH
OH
OH
COOH
OP
COOH
O
CH2OP
OH
OH
HOH
H
COOH
OHOH
OH
OH
H
COOHOHOH
O
H
H
COOHOHOH
H
HOH
H
COOHOHOH
H
POH
H
COOHOH
H
PO
COOH
H
H
COOHOH
COOH
H COOH
OH
COOHO
COOH
O
COOH
NH2
Ery-4-P PEP7P-2-Dehydro-3-deoxy-D-arabino-heptulosonat
3-Dehydro-chinat 3-Dehydro-schikimat
SchikimatSchikimat-5-PO5-(1-carboxyvinyl)-3-P-schikimat
Chorismat
Prephenat Phenylpyruvat Phenylalanin
H COOH
OH
COOHO
Arogenat
(NAD)
NADH
ATP
PEP
FMN/NADH
CO2, H2O Glu KG
Pi H2O
PiCOOHCOOH
OO
![Page 71: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/71.jpg)
H. Scheer
Phenylpropanoide in Pflanzen
Aus G. Michal:BiochemicalPathways, Wiley, 1999
![Page 72: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/72.jpg)
H. Scheer
Lignin
Aus D.E.Metzler:BiochemistryAcademic Press, 2003
![Page 73: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/73.jpg)
H. Scheer
Einige Stilbene und Flavonoide
OHHO
Pinosylvin
O
O
O
RhaGlc
OH
OH
HO
HO
H
Rutin (Quercetin Glykosid)Cyanidin; Dephinidin (5'-OH); Petunidin (3'-OCH3, 5'-0H)
O
HO
OH
OH
HO
HO
+
O O
OH
CH3O
HO GlcRha
Hesperidin
OH
OH
HO
HO
O
Phlorhizin
1'2'
3'
4'5'
2
3
4 56
78
Peonidin (3'-OCH3); Malvidin (3',5'-OCH3); Pelargonidin (3'-H)
*
**: glykosiliert in Anthocyanen
Stilben Flavonol Anthocyani(di)ne
O
FlavonChalcon
(Blütenfarbstoffe)(Antioxidant (Radikalfänger), bakterizid, viruzid)
(Antioxidant, Radikalfänger)(Nierengift)
![Page 74: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/74.jpg)
H. Scheer
pH-Effekt bei Anthocyanen
O
HO
OH
OH
HO
HO
+O
HO
OH
OH
HO
HO
OH
O
HO
OH
OH
O
HO
O
HO
O
OH
O
HO
O
HO
OH
OH
HO
HO-
OH
pH >3 pH 4-5 pH 6-7
pH 7-8pH >8
![Page 75: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/75.jpg)
H. Scheer
Metallkomplexe von Anthocyanen
Aus Wikipedia
![Page 76: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/76.jpg)
H. ScheerWikipedia Abbildung von User Chris 73, frei verfügbar unter http://commons.wikimedia.orf/wiki/image:Urakuen_tea_garden_03.jpg under thze creative commons cc-by-
sa2.5 licenceschriftfarbe
![Page 77: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/77.jpg)
H. Scheer
Funktionen
• Lichtschutz a) Passiv UV- und Blau-AbsorptionFlavonoide b) Aktiv Quencher von Radikalen (wasserlöslich)
• Lock-Pigmente BlütenfarbenAnthocyane
• Abwehr a) Bakterizide, Fungizide, Viruzide Lignane (a,b) b) Fraßgifte
Stilbene (a) c) Schlechter GeschmackCumarine (a,b,d)d) Phototoxizität
Flavonoide (a) (z.B. Hemmung Mitose, PDase, Atmung, StörungTannine (a,b) des Hormonhaushalts, Proteinbindung)
• Festigung Druckstabile Strukturen, zusammen mit Lignin zugstabiler Cellulose Verbundwerkstoff
• Sperrschichten Gas- und Wasser-undurchlässigSuberin, Cutin
![Page 78: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/78.jpg)
H. Scheer
Modularer Aufbau von Polyketiden: II
S-CoA
HOOC
O
S-CoA
OS-CoA
Kette
O
S-CoA
O
Kette
O
S-CoA
O
R
OH
S-CoA
O
R S-CoA
O
R
CO2
Ketoacyl-Synthase Ketoreductase Dehydratase Reductase
Fettsäure-Synthese
Polyketid-Synthese
R R R R
![Page 79: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/79.jpg)
H. Scheer
Modularer Aufbau von Polyketiden: 1
AT: AcyltransferaseACP: Acyl-carrierKS: Ketoacyl- SynthaseKR: KetoreductaseDH: DehydrataseER: EnoylreductaseTE: Thioesterase
Aus D.E.Metzler:BiochemistryAcademic Press, 2003
![Page 80: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/80.jpg)
H. Scheer
Polyketide: Urushiol
Aus D.E.Metzler:BiochemistryAcademic Press, 2003
![Page 81: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/81.jpg)
H. Scheer
Polyketide: DiverseAus D.E.Metzler:BiochemistryAcademic Press, 2003
![Page 82: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/82.jpg)
H. Scheer
Polyketide: Tetracyclin
Aus D.E.Metzler:BiochemistryAcademic Press, 2003
![Page 83: Phytochemie P. Braun / H. Scheer WS 2007 / 2008](https://reader035.vdocuments.net/reader035/viewer/2022062518/56814611550346895db31f1a/html5/thumbnails/83.jpg)
H. Scheer
Polyketide: Griseofulvin
Aus D.E.Metzler:BiochemistryAcademic Press, 2003