Sintesis Antibiotik: -laktam
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Sintesis Antibiotik b-Laktam Didin Mujahidin
Beberapa Antibiotik b-Laktam H N Penicillium notatum
H2N
S
O
N
N
O
O OH
O
O 6-APA
Penisilin G
OMe H N OMe O
O N
S
N
O
O O
S N
OH
O
O
O
O
O NH2 H N
O
S
O
O OH
NH
O
N O pivampisilin
H N NH O
S
O
N
azlosilin O
H N
OH
amoksisilin
N
NH
N
OH
NH N
S
O
ampisilin
kloksasilin
H N
O
HO
O
OH
metisilin
NH2
H N
S
O
O
OH
NH2
H N
Cl
N
S
O
O
H N
O
S N
O pirbenisilin
O
OH
Jenis lain b-laktam O H2N
S
S
S
O
O
O OH
O
OH
O
O
6-APA
OH
tazobaktam OH
O
N N N
N
N
N
O
OH O
EtOOC
COOEt
NH O
COOPG
N O
S
CO2N+ N biapenem N
Amoksisilin NH2
HO
H N
O
S N
O O
OH
Menuju Intermediet asam 6-aminopenisilat (6-APA)
Penisilin G
TMS -6-APA
Amoksisilin NH2
HO
H N
O
S N
O O
OH
Sintesis 4-Hidroksifenilglisin rute 1 O
OH
OH
+
HO
HO H
fenol
1. NH3 2. kristalisasi
NH2 HO
O
OH
asam glioksilat
OH
O asam p-hidroksimandelik
O 4-hidroksifenilglisin
rute 2 O H fenol
NH2
+
+
HO
O
OH
-
O
O
HO
.NH4+
OH O 4-hidroksifenilglisin
asam glioksilat
rute 3 O +
HO
+ H
fenol
O
H O
glioksal
H2N
HN NH2
urea
HO
O
H2O
NH
O 5-(4-hydroxyphenyl) imidazolidine-2,4-dione
NH2 HO
OH
O 4-hidroksifenilglisin
Rute Detail Amoksisilin
Na-4-hidroksifenilglisin
D-p-Hidroksifenilglisin Dane salt
Amoksisilin
gas alam
Bioetanol
O propilen CaO
Batubara
OH
OC2H5 HO etil asetoasetat
HO
Reppe
O OC2H5 NH O
NH2 asetilen
benzena
O
Reforming
fenol
O-.K+ O Garam Dane
OH O 4-hidroksifenilglisin
aseton
Minyak Bumi
Nafta
Fermentasi
6-APA
NH2 O HO
H S N
O O
Amoksisilin
COOH
O OH Bioetanol
esterifikasi
oksidasi OH asam asetat
O basa O etil asetat
O
O
OH asetoasetat
Sintesis Fenol
Beberapa Antibiotik b-Laktam H N Penicillium notatum
H2N
S
O
N
N
O
O OH
O
O 6-APA
Penisilin G
OMe H N OMe O
O N
S
N
O
O O
S N
OH
O
O
O
O
O NH2 H N
O
S
O
O OH
NH
O
N O pivampisilin
H N NH O
S
O
N
azlosilin O
H N
OH
amoksisilin
N
NH
N
OH
NH N
S
O
ampisilin
kloksasilin
H N
O
HO
O
OH
metisilin
NH2
H N
S
O
O
OH
NH2
H N
Cl
N
S
O
O
H N
O
S N
O pirbenisilin
O
OH
Jenis lain b-laktam O H2N
S
S
S
O
O
O OH
O
OH
O
O
6-APA
OH
tazobaktam OH
O
N N N
N
N
N
O
OH O
EtOOC
COOEt
NH O
COOPG
N O
S
CO2N+ N biapenem N
Amoksisilin NH2
HO
H N
O
S N
O O
OH
Menuju Intermediet asam 6-aminopenisilat (6-APA)
Penisilin G
TMS -6-APA
Amoksisilin NH2
HO
H N
O
S N
O O
OH
Sintesis 4-Hidroksifenilglisin rute 1 O
OH
OH
+
HO
HO H
fenol
1. NH3 2. kristalisasi
NH2 HO
O
OH
asam glioksilat
OH
O asam p-hidroksimandelik
O 4-hidroksifenilglisin
rute 2 O H fenol
NH2
+
+
HO
O
OH
-
O
O
HO
.NH4+
OH O 4-hidroksifenilglisin
asam glioksilat
rute 3 O +
HO
+ H
fenol
O
H O
glioksal
H2N
HN NH2
urea
HO
O
H2O
NH
O 5-(4-hydroxyphenyl) imidazolidine-2,4-dione
NH2 HO
OH
O 4-hidroksifenilglisin
Rute Detail Amoksisilin
Na-4-hidroksifenilglisin
D-p-Hidroksifenilglisin Dane salt
Amoksisilin
gas alam
Bioetanol
O propilen CaO
Batubara
OH
OC2H5 HO etil asetoasetat
HO
Reppe
O OC2H5 NH O
NH2 asetilen
benzena
O
Reforming
fenol
O-.K+ O Garam Dane
OH O 4-hidroksifenilglisin
aseton
Minyak Bumi
Nafta
Fermentasi
6-APA
NH2 O HO
H S N
O O
Amoksisilin
COOH
O OH Bioetanol
esterifikasi
oksidasi OH asam asetat
O basa O etil asetat
O
O
OH asetoasetat
Sintesis Fenol
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