Download - mekanisme pembentukan terpen/steroid
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KIMIA ORGANIK BAHAN ALAM (KOBA)
Terpen / Steroid
^__^
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CO2 + H2O
Photosynthesis Glucose Carbohydrates
G
L
Y
C
O
L
Y
S
I
S
Acetyl CoA
Citric Acid
Cycle
Fatty Acids
Lipids
Acetogenins
Terpenes
Steroids
Building Blocks
Amno Acids
Proteins
synthesis
enzymes
regulationNucleic
Acids
reproduction
Alkaloids
Phenyl-
propanoids
RNA DNA
PRIMARY METABOLISM
SECONDARY
METABOLISM
SECONDARY
METABOLISM
hn
CO2 + H2O + ATP
Flavonoids
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TERPENOID
golongan senyawahidrokarbon yang tersusun
oleh unit-unit isoprene
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Reaksi Pembentukkan Isoprene (Jalurmevalonat / Mevalonic acid pathway)
1. Pembentukkan Asam mevalonat
H3C C
O
SCoA
Asetil CoA
H3C C
O
SCoA
H3C C
O
SCoAElektrofil
Suasana asam
Suasana basaHC C
O
SCoA
H
H
OH
H2C C
O
SCoA
Nukleofil
a.
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b.
H3C C
O
SCoAElektrofil
H2C C
O
SCoA
Nukleofil
+
H3C C
O
SCoA
H2C C
SCoA
O
H3C C
O
H2C C
SCoA
O
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H3C C
O
H2C C
SCoA
O
H2C C
O
SCoA
Nukleofil
+ H3C C
OH
H2C C
SCoA
O
CH2
C
OCoAS
H+
CH3
C
OH
H2C C
SCoA
O
H2CC
O
CoAS
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CH3
C
OH
H2C C
SCoA
O
H2CC
O
CoAS
dihidrolisismenjadikarboksilat
dihidrolisis dandireduksi menjadi
alkohol
CH3
C
OH
H2C CH2
OH
H2CC
O
HO
Asam Mevalonat
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2. Dekarboksilasi (penghilangan gugus karboksilat)CH3
C
OH
H2C CH2
OH
H2CC
O
OH
CH3
C
O
H2C CH2
OH
H2CC
O
O
HH
CH3
COH2C CH2
OH
H2CC
O
O
HH
++
ATP
H3C
CH2C CH2
OPP
H2CO P
OH
O
O P
O
OH
OH
-OPP IPP
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3. IPP dan DMAPP
H3C
C CH
CH2
OPP
H2CH
H3C
C CH
CH2
OPP
H3C
IPP(isopentenyl pyrophospat)
DMAPP(dimetilalil pyrophospat)
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OPP
IPP
OPP
DMAPP
isoprene
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Penggabungan unit –unit isoprene
• Kepala dengan ekor (yang sering terjadi)• Ekor dengan ekor
OPP
kepalaekor
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Mekanisme penggabunganisoprene (kepala dengan ekor)
OPP OPP
+H
OPP
ikatan baru
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Mekanisme penggabungan isoprene (ekordengan ekor)
O P
O
O
H2C
O
O
PO
O
O
H2C
O
PO
O
O
H2C
CH2PPO
O
PO
O
O
CH
H2C
H
O
PO
O
O
HC
H2C
H2C
H2C
ikatan baru
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Unit isoprene tersebut dapat membentuk siklikContoh:
OPP
OPP
OPP
H
OPP
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KLASIFIKASI TERPENOIDJENIS TERPEN JUMLAH ATOM C JUMLAH
ISOPRENE
Hemiterpen 5 1Monoterpen 10 2Sesquiterpen 15 3Diterpen 20 4Sesterpen 25 5Triterpen 30 6Tetreterpen 40 8
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Contoh Senyawa Terpenoid1. Monoterpen
CH2OH
geraniol(pada bunga rose)
OH
menthol(pada papermint)
O
camphor(pohon camphor)
pinen
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2. sesquiterpen
H3C
CH
CH3
H3C
CH3
geranium oil
HO
farnesol
bisabolen
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3. diterpen
OH
manool
piramic acid
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4. sesterterpen
HOOC
gascardic acid
OH
ophiobolin F
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5. triterpen
dammarane
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6. tetraterpen
-carotene
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REAKSI PADA
SENYAWA TERPENOID
H H
OH
H
O
H
O
geraniol geranial -mycrenehops
nerallemon oil
OH OPP
OPP
OPP
citronellol geranyl-pp (GPP) linalyl-pp (LPP) neryl-pp (NPP)
H
O
OH
OH
OH
citronellal-terpenol linalool nerol
1
23
4
5
6
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MEKANISME1 OPP
H-OH / H+
OPP
H
H
OH
OH
H
OH
H
oksidasi
H
O
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2 OPP
H-OH / H+
OPP
H
O
H
H
O
H H
OH
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3 OPP
H-OH / H+
OPP
H
OH
HO
H
H
OH
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4
OPP OPP
H
H+
HH
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5
OPP
OPP
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6
OPP
H-OH / H+
OPP
H
H
OH
OH
H
OH
H
oksidasi
H
O
H H
H
O
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STEROID
Turunan dari 1,2-siklopentanoperhidrofenantren
perhidrofenantren
sikloheptano
1
2
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Pembentukkan skualenCH2PPO H2C
OPP
FPP
FPP
H2C
H2C
skualen
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MEK
ANISM
EH2C
OP
O
O
O
H2CO
P
O
O
O
H2C O P
O
O
O
CH2PPO
+
FPP
FPP
H2C
CH
H
O
O
PO
H2C
HC
O
O
PO
H2C
H2
C
skualen
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Epoksidasi skualen denganflavoprotein
skualen
O
O
flavoprotein
NADPHO
O
O
O H+
O
OH
H
O
HHO
karbokation
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Skualen(perkusor pembentukkan steroid)
Steroid hewan (lanosterol)
Steroid tumbuhan (sikloartenol))
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Pembentukkan steroid
hewan(lanosterol)
karbokationHO
siklisasi
H3C CH3
CH3CH3
HO
CH3
CH3
- eliminasi
- hidrogen dan metil shift
H3C CH3
CH3
HO
CH3
CH3H
lanosterol
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SIKLOARTENOL
HO
HO
siklisasi
- eliminasi- hidrogen dan metil shift
karbocation
HO
H3CCH3
CH 2
CH3
CH3
CH3
H
H
sikloartenol
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HO
CH3
CH3
CH3
H
HO
CH3
CH3
CH3
O
HO
CH3
CH3O
Contoh Steroid Hewan
cholesterol
pregnenolopeestone
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Contoh Steroid Tumbuhan
HO
HO
O
O
sigmaterol
diosgenin