Download Nitrogen Metabolism

Nitrogen Metabolism
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N2 + 3 H2
G´° = ––33.5 kJ/mol
NH3
N2
2 NH3
NO2
NO3
ADP
+ Pi
NH3
NO2
Nitrite
H2O reducing
5H
enzyme
Cytoplasm
ATP
ATP
Synthase
NH2OH
OH
4 e––
Anammoxosome
H2O
O
Hydrazine
hydrolase
N2H4
4H
Hydrazine
oxidizing
enzyme
N2
Pentacycloanammoxic acid
4 CoA-SH
+ 4 pyruvate
4 CO2
+ 4 acetyl-CoA
>16 ATP
8 e–– +
4 H2X
+ many h
N N
+8H
2 X2
Nitrogenase from Azotobacter vinlandii pdb ID 1M1N
Nitrogen Assimilation
>16 ADP
+ >16 Pi
Nitrogenase
complex
2 NH3 + H2
O
O
NH4
O
H2O
O
NAD(P)H NAD(P)
O
NH2
O
O
O
Glutamate
Dehydrogenase
O
O
NH3
Glutamate
Dehydrogenase
O
O
Glutamate
-Ketoglutarate
O
O
ATP
O
ADP
H3N
O
NH4
O P O
H3N
Glutamine
Synthetase
O
O
O
O
Pi
Glutamine
Synthetase
O
O
O
Glutamine
O
O
NH2
H3N
O
O
NADPH
NADP
O
+
H3N
Glutamine
Glycine
Alanine
CTP
Histidine
O
AMP
Glucosamine-6-phosphate
Carbamoyl phosphate
NADH
+
N5,N10-Methylene
Tetrahydrofolate
NAD
+
THF
NH3
NH4
Glycine
cleavage enzyme
(Glycine synthase)
O
O
Glycine
O
O
Glutamate
synthase
O
O
(Glutamate:
-Ketoglutarate
Glutamate
oxo-glutarate
aminotransferase
{GOGAT})
O
O
O C O +
NH2
H3N
O
Glutamate
O
O
+
O
H3N
O
O
Glutamate
Oxaloacetate Family
3-Phosphoglycerate Family
O
OH
H3N
NH3
O
O
Glycine
NH2
H3N
H3N
O
O
Serine
O
O
O
O
Aspartate
O
O
Asparagine
-Ketoglutarate Family
O
O
NH2
O
O
N
H2
O
Proline
H3N
O
Pyruvate Family
H3N
O
Glutamate
O
H3N
O
Glutamine
O
O
Alanine
O
Erythrose4-phosphate
O
C O
O C
H
O P O
O C
+
O O
H2O
O H C OH
CH2
O P O CH2
Phosphoenolpyruvate
O
Pi
HO
H C OH
2-Keto-3-deoxyD-arabinoheptulosonate
7-phosphate synthase
O H C OH
O P O CH2
3-Dehydroquinate O
synthase
[NAD]
O
2-Keto-3-deoxyD-arabinoheptulosonate
7-phosphate
OH 3-Dehydroquinate O
dehydratase
OH
O
O
C O
C O
Pi
Pi
O
O P O
O C C O
OH
CH2
Chorismate
synthase
O
NADPH
Shikimate
dehydrogenase
OH
5-Enolpyruvylshikimate
3-phosphate
Chorismate
3
steps
5
steps
O
O
O
C C O
C O
C O
ADP
CH2
ATP
O
O P O
5-Enolpyruvylshikimate
3-phosphate
synthase
OH
O
OH
Shikimate
3-phosphate
HO
Shikimate
kinase
OH
OH
Shikimate
OH
O
3
steps
O
O
H
N
O
P O
O
H3N
H
N
NADP
O O
O C C O
O
OH
OH
3-Dehydroshikimate
3-Dehydroquinate
O
PhosphoenolO P O pyruvate
CH2
C O
H2O
C O
HO C H
H C OH
C C O
O
O
CH2
Pi
N-phosphonomethyl
glycine (glyphosate)
O
H3N
H3N
O
O
O
O
O
Cl
Cl
O
O
O
OH
Cl
(2,4-Dichlorophenoxy)acetic acid
(2,4-D)
Cl
O
OH
OH
CH3
(4-Chloro-2-methylphenoxy)acetic acid
(MCPA)
O
CH3
Cl
3,6-Dichloro-2-methoxybenzoic acid
(dicamba)
Heme Biosynthesis
O
O
Glycine
O
H3N
O
O
CoA-SH
O
O
O
O
CO2
O
-Amino
levulinic acid
synthase
CoA
Succinyl-CoA
O
O
-Amino
levulinc acid
(ALA)
NH3
-Amino
levulinic acid
synthase
NH3
O
Porphobiligen
synthase
O
NH
HN
NH
HN
2 CO2
Coporphyrinogen
oxidase
O
O
O
4 NH4
4 CO2
Uroporphyrinogen
decarboxylase
Uroporphyrinogen
III
cosynthase
Fe2+
O
O
N
N
O
O
Protoporphyrin IX
N
Fe2+
Ferrochetalase
HN
N
O
O
Porphobiligen
deaminase
NH
NH3
Porphobiligen
O
Protoporphyrinogen
oxidase
NH
O
N
N
O
O
O
O
Iron-Protoporphyrin IX
Heme Breakdown
N
O2
N
CO
+
Fe3+
Fe3+
O
NH
N
N
O
Biliverdin
HN
H
N
N
Heme oxygenase
O
O
O
O
O
O
O
O
NADPH
Iron-Protoporphyrin IX
Biliverdin
reductase
NADP
O
NH
O
Bilirubin
H
H
N
H
O
HN
N
O
O
O
OH
OH
NADPH
NADP
OH
DOPA
decarboxylase
[PLP]
Tyrosine
H3N
hydroxylase
[tetrahydrobiopterin]
H3N
O
O
O
Tyrosine
OH
CO2
Dopamine
-hydroxylase
H3N
O
CH3
O
S
O
OH
S-adenosyl methionine
Phenylethanolamine
N-methyltransferase
(PNMT)
S-adenosyl
homocysteine
N
N
OH
Norepinephrine
NH2
N
OH
H3N
Dopamine
DOPA
S-adenosyl methionine
Dehydroascorbic
acid
Ascorbic
OH acid
N
OH
CH2 O
OH
NH3
OH
CH3
OH
H2N
OH
Epinephrine
S-adenosyl
homocysteine
OH
O
OH
Catechol-O-Methyl
H3N
Transferase
OH
NH3
Monamine Oxidase B
[flavin]
Dopamine
3-O-methyl
dopamine
OH
O
H
3,4-dihydroxyphenyl
acetaldehyde
CH3
CH3
O
O
O
N
N
CH3
CH3
Meperidine
(Demerol)
O2
CH3
H3N
O
H2O2
OH
S-adenosyl
methionine
Monoamine
oxidase
H+
Heat
N
N
N
CH3
CH3
CH3
N-Methyl-4-phenyl
1-Methyl-4-propionoxy
1,2,3,6 tetrahydropyridine
piperidine
(MPTP)
(MPPP)
MPDP
+
1-Methyl-4-phenyl
pyridinium
(MPP+)
OH
OH
NADPH
NADP
O
OH
O
HO
Tyrosine
H3N
hydroxylase
[tetrahydrobiopterin]
H3N
O
O
O
Tyrosine
Tyrosinase
Non-enzymatic
H3N
O
O
O
Tyrosinase
DOPA
H
N
N
H
HO
O
O
O
Non-enzymatic
O
N
H
O
Melanin
N
H
O
I
OH
OH
H2O2
+
I
Thyroglobulin
Thyroid
peroxidase
OH
I
O
I
Thyroglobulin
I
I
I
Thyroid
peroxidase
Thyroglobulin
Lysosomal
proteases
I
OH
O
I
I
H3N
O
I
Thyroxine
O
NH2
HN
H3N
O
C
NH2
NADPH
+ O2
HO
NADP
+ H2O
HN
Nitric oxide
H3N
Arginine
synthase
[FAD]
[FMN]
O
O
[tetrahydrobiopterin]
NH
1/
C
+ O2
NH2
N-Hydroxyarginine
O
2 NADPH
O
1/ NADP
2
+ H2O
Nitric oxide H3N
synthase
[FAD]
[FMN]
O
[tetrahydrobiopterin]
HN
Citrulline
O
Glu371
Tetrahydrobiopterin
Trp457
Cys194
NH2
+
Arginine
(Substrate)
Heme
C
N O
Nitric
oxide
NH3
O
NH2
HN
C
O
NH2
Glycine
NH2
HN
C
S-adenosyl
methionine
H3C
NH2
O
H3N
Amidinotransferase
Arginine
NH2
N
O
C
NH2
O
Guanidinoacetate
methyl
transferase
O
Creatine
Guanidinoacetate
O
O
NH3
S-adenosyl
homocysteine
H3N
Ornithine
O
ATP
O
Creatine kinase
ADP
O
O P O
O
NH
H
N
H3C
C NH2
N
Creatinine
CH3
O
Glutamate
Non-enzymatic
Phosphocreatine
O
H3N
H3N
Glutamate
decarboxylase
[PLP]
O
+ CO2
-Aminobutyric acid
(GABA)
N
N
NH
Histidine
Histamine
H3N
O
N
S
Histidine
decarboxylase
[PLP]
O
H
N
NH
H
N
N
Cimetidine
C
N
C
H3N
NH2
O
O
O
O
N
NH
+ CO2
O
Polyamine Synthesis
NH2
Adenosine Triphosphate
(ATP)
N
N
O
O
O
N
N
O
H3N
O
H
OH
O
O
Methionine
OH
Methionine
adenosyl
transferase
S
O
O
NH2
N
N
+
CH2 O
NH3
OH
NH3
O
Ornithine
CH3
H3N
Ornithine
decarboxylase
[PLP]
S
Putrescene
OH
H3N
Decarboxylated
S-Adenosyl
methionine
NH2
H2N
NH3
Spermine
Spermine
synthase
O
CO2
N
N
CH2 O
NH3
Spermidine
synthase
H3N
OH
NH2
5´-Methyl
adenosine
NH2
H3C S
N
N
CH2 O
N
N
NH3
Spermidine
O
O
Pyrophosphate
OH
5´-Methyl
adenosine
+
O P O P OH
NH2
Decarboxylated
S-Adenosyl
N
N
methionine
H3N
O
Inorganic
phosphate
O
NH3
S-Adenosyl
methionine
decarboxylase
O
O P OH
N
N
CH3
O
+
O P O P O P O CH2 O
O
S
S-Adenosyl
methionine
CH3
OH
OH
NH3
O
Enzyme
O
H
C
H
H
N
CH
HO
Ornithine
NH2
O
O
N
CH3
O
Enzyme C H
O
H
NH
N
H
CH
HO
O P O
NH3
NH3
CH3
H
O
Enzyme
NH2
O
O P O
C
H
NH
CH
O
HO
O
N
O
CH3
H
O P O
O
N
H
NH3
Enzyme
H
+ CO2
NH2
NH
CH
O
HO
CH3
O P O
O
N
H
NH3
Enzyme
O
F F
O
CH
C
H
H
N
CH
HO
CH3
DFMO
NH2
O
F F
O
Enzyme C CH
O
H
NH
N
H
CH
HO
O P O
O
N
NH3
NH3
CH3
H
Enzyme
NH2
O
O P O
N
O
F F
O
CH
C
NH
CH
O
HO
O
CH3
H
O P O
O
N
H
NH3
NH3
O
F F
O
CH
C
NH3
Difluoromethyl
ornithine
(DFMO)
F
Enzyme
+F
HC
+ CO2
NH2
NH
CH
HO
CH3
O
O P O
N
H
O