Download Amino Acid Structures

Amino Acid Structures
S
O
O
H3N
O
H3N
O
Alanine
Ala
A
O
H3N
O
H3N
O
Valine
Val
V
O
Leucine
Leu
L
H3N
O
Isoleucine
Ile
I
O
Methionine
Met
M
OH
NH
O
O
H3N
O
H3N
O
Phenylalanine
Phe
F
H3N
O
Tyrosine
Tyr
Y
O
Tryptophan
Trp
W
H2N
O
NH2
OH
OH
O
H3N
O
O
O
H3N
H3N
O
Serine
Ser
S
O
Asparagine
Asn
N
O
Threonine
Thr
T
O
Glutamine
Gln
Q
H2N
NH3
O
O
O
H3N
NH2
NH
O
N
NH
O
O
H3N
O
H3N
O
Aspartate
Asp
D
O
H3N
O
Lysine
Lys
K
O
Glutamate
Glu
E
O
H3N
O
H3N
O
Arginine
Arg
R
O
Histidine
His
H
SH
O
H3N
O
Glycine
Gly
G
N
H2
O
Proline
Pro
P
O
O
H3N
O
Cysteine
Cys
C
HO CH2
Glycolysis
O OH
OH
OH
OH
ATP
Hexokinase
Glucokinase
ADP
O
O OH
O
OH
O P O CH2 O
Phosphoglucoisomerase
O
OH
Fructose1,6-bisphosphate
O P O CH2 O
O
3-phosphoglycerate
Phosphofructokinase
O
CH2 O P O
O
HO
OH
Aldolase
OH
O
O
O P O
Phosphoglycerate
kinase
H C OH
CH2 O
O
O
C O
GlyceraldehydeH C O
3-phosphate
dehydrogenase H C OH
CH2 O
H C OH
O P O
ATP
Phosphoglycerate
mutase
O
ADP
CH2 O
NADH
O P O
O
1,3-bisphosphoglycerate
NAD
+
Pi
O P O
O
Glyceraldehyde
3-phosphate
C O O
H C O P O
O 2-phosphoglycerate
Enolase
H2O
O
C O O
ADP
ATP
C O P O
CH2
O
Phosphoenol
pyruvate
OH
NADH
NAD
C O
CH3
Pyruvate
OH
C O
HO C H
C O
Pyruvate
kinase
OH
ADP
O
OH
HO
ATP
Glucose-6-phosphate
C O
CH2 OH
OH
OH
CH2
Fructose-6-phosphate
O
O P O CH2
Lactate
dehydrogenase
CH3
L-Lactate
H
DihydroxyHO C H acetone
phosphate
O C
CH2 O
O P O
O
Triose
phosphate
isomerase
HO CH2
Fermentation
O OH
OH
OH
OH
ATP
Glucose
Hexokinase
O
ADP
O OH
O
OH
Fructose-6-phosphate
O
O P O CH2
O P O CH2 O
Phosphoglucoisomerase
O
HO
OH
OH
OH
ATP
O
Fructose1,6-bisphosphate
O P O CH2 O
O
3-phosphoglycerate
Phosphofructokinase
O
CH2 O P O
O
HO
OH
Aldolase
OH
O
O
O P O
Phosphoglycerate
kinase
H C OH
CH2 O
O
O
C O
GlyceraldehydeH C O
3-phosphate
dehydrogenase H C OH
CH2 O
H C OH
O P O
ATP
Phosphoglycerate
mutase
O
CH2 O
NADH
O P O
ADP
OH
ADP
Glucose-6-phosphate
C O
O
1,3-bisphosphoglycerate
NAD
+
Pi
O P O
H
DihydroxyHO C H acetone
phosphate
O C
CH2 O
O P O
O
Triose
phosphate
isomerase
O
Glyceraldehyde
3-phosphate
C O O
H C O P O
CH2
OH
O 2-phosphoglycerate
Enolase
H2O
O
C O O
ADP
OH
ATP
C O
C O P O
CH2
O
Phosphoenol
pyruvate
CH2 OH
C O
Pyruvate
kinase
CH3
Pyruvate
Pyruvate
decarboxylase
CO2
NAD
H
C O
Acetaldehyde
NADH
CH3
H
Alcohol
dehydrogenase
H C OH
CH3
Ethanol
Tricarboxylic Acid Cycle
O
Acetyl-CoA
H3C C S CoA
Oxaloacetate
Malate
O
8
OH
O
O
O
NAD
O
FADH2
O
O
CoA-SH
NADH
O
O
C
O
O
cis-Aconitate
O
H2O
O
2
H2C
O
C
O
O
O
O
O
H2C
6. Succinate Dehydrogenase
HO
O
H2C
C
CoA
O
O
O
Isocitrate
3
NADH
O
NADH
H2C
O
NAD
+
C
CoA-SH H2C
O
O
O
Succinyl-CoA S
C
O
O
NAD
GDP + Pi
CoA-SH 5
H2O
2
GTP
O
O
4. α-Ketoglutarate Dehydrogenase
5. Succinyl-CoA Synthetase
7. Fumarase
8. Malate Dehydrogenase
FAD
Succinate
O
H2C
HO
3. Isocitrate Dehydrogenase
O
Fumarate
6
O
1
1. Citrate Synthase
2. Aconitase
O
O
O
O
7
H2O
Citrate
O
O
4
O
CO2
O
O
α-Ketoglutarate
C
O
O
O
Oxalosuccinate
3
CO2
O
O
O
O
Dihydroxyacetone
phosphate
O P O
O
Fructose
1,6-bisphosphate
O P O
CH2 O
CH2 O
O C
O C
Aldolase
HO C H
HO C H
Cleavage occurs
between C3 and C4
(β to the carbonyl)
H C OH
H C O
H C OH
H C OH
CH2 O
CH2 O
Glyceraldehyde
3-phosphate
O P O
O
NAD
+
CoA-SH
Pyruvate
+
CO2
Acetyl-CoA
O
H3C C C O
Oxalosuccinate
O
O
O
O
Isocitrate
dehydrogenase
O
C
O
O
α-Ketoglutarate
O
O
O
CO2
O
C
O
H3C C S CoA
Pyruvate
dehydrogenase
O
O
O P O
NADH
O O
O
+
H
NAD
+
CoA-SH
O
NADH
O
+
CO2
O
O
C
O
α-Ketoglutarate
α-Ketoglutarate
dehydrogenase
C
S
CoA
Succinyl-CoA
O
Glucose
Glucose Metabolism
ATP
Pi
(Glycolysis, Gluconeogenesis, & Glycogen Synthesis)
Hexokinase
Glucokinase
Glucose-6phosphatase
ADP
Phosphoglucomutase
Glucose
Glucose-6-phosphate
1-phosphate
Phosphoglucoisomerase
UDP-glucose
pyrophosphorylase
Fructose-6-phosphate
PPi
UDP-Glucose
Phosphofructokinase
Fructose
bisphosphatase
Pi
Glycogen
UTP
ATP
Pi
Glycogen
Phosphorylase
Glycogen
synthase
Pi
ADP
Fructose-1,6-bisphosphate
Triose phosphate
isomerase
Aldolase
Dihydroxyacetone
Glyceraldehyde
+
phosphate
3-phosphate
NAD + Pi
NADH
Glyceraldehyde-3-phosphate
Glycerol-3-phosphate
dehydrogenase
dehydrogenase
NADH
NAD
Glycerol
1,3-Bisphosphoglycerate
Glycerol
kinase
Glycerol
ADP
3-phosphate
Phosphoglycerate
kinase
ADP
ATP
ATP
3-Phosphoglycerate
Phosphoglycerate
mutase
2-Phosphoglycerate
Enolase
Phosphoenolpyruvate
carboxykinase
Oxaloacetate
Phosphoenolpyruvate
ADP
GDP
+ CO2
Pyruvate
kinase
NAD
Lactate
Malate
dehydrogenase
NAD
ATP
NADH
Malate
Pyruvate
Lactate
dehydrogenase
Pyruvate
carboxylase
Alanine
NADH
GTP
Pyruvate
Aminotransferase
CoA-SH + NAD
Pyruvate
dehydrogenase
ATP
+ CO2
CO2 + NADH
Acetyl-CoA
Malate
NAD
Malate
dehydrogenase
NADH
Oxaloacetate
ADP
+ Pi
Citrate
Citrate
synthase
TCA Cycle
Citrate
Major Metabolic Pathways
Glycogen
Glycogen
synthase
Glycogen
Phosphorylase
Glucose
CO2 +
NADPH NADP
NADP
Hexokinase
Glucokinase
NADPH
Glucose-6-phosphate
Ribulose-5-phosphate
Fructose-6-phosphate
Glycerol
phosphate
Ribose-5-phosphate
Ribose-5-phosphate
pyrophosphokinase
Glucose-6-phosphate
dehydrogenase
Glucose-6phosphatase
Fructose
bisphosphatase
Phosphofructokinase
Fructose-1,6-bisphosphate
PRPP Glutamyl
amidotransferase
Fructose-6-phosphate
+
Glyceraldehyde-3-phosphate
Nucleotides
Carbamoyl
phosphate
synthetase II
Fructose
Glycerol
HCO3
N5, N10
e yl Methylene
rin eth
e
S ym se
THF
ox fera
dr
hy rans
Glycine
t
synthase
DihydroxyGlyceraldehyde
acetone +
3-phosphate
phosphate
and
Triacyl
glycerols
Serine
3-Phosphoglycerate
Fatty acids
Cholesterol
P
H
A
D
N
Alanine
en
zy
Oxaloacetate
Aspartate
Amino acids
Transcription
Translation
L-Lactate
ic
Citrate lyase
Pyruvate
M
al
Citrate
Phosphoenol
pyruvate
carboxykinase
N
A
D
P
Acetyl-CoA
Pyruvate
kinase
Phosphoenolpyruvate
Aspartate
Glutamine
Glycine
m
e
Acetyl-CoA
carboxylase
HMG-CoA
Reductase
Nucleic acids
Pyruvate
Pyruvate
dehydrogenase
Pyruvate
carboxylase
Malate
NADH
Fumarate
+
CO2
ATP
+
β
id
- ox
at
Cysteine
Glycine
Serine
Threonine*
Tryptophan*
ion
Protein folding
Post-translational modifications
Proteins
Fatty acids
Asparagine
NADH
+
Ketone
bodies
Acetoacetyl-CoA
Cytoplasm
Malate
Mitochondrial
Matrix
Leucine*
Lysine
Phenylalanine*
Tryptophan*
Tyrosine*
Oxaloacetate
CoA-SH
NAD
H
Citrate
H
ATP
synthase
NAD
+ H2O
Citrate
synthase
Aspartate
Amino acids
O2
Isoleucine*
Leucine*
Threonine*
Acetyl-CoA
CO2
Ubiquitin conjugation,
Proteolysis
Electron
transport
Membrane
lipids
Replication
and
Transcription
Nucleases
ATP
ADP
+ Pi
H
NADH
cis-Aconitate
Mitochondrial
Matrix
Cytoplasm
Fumarate
NH4 + HCO3
FADH2
Isocitrate
dehydrogenase
CoA-SH
+
GTP
GDP + Pi
Isoleucine*
Methionine
Valine
Threonine*
Propionyl-CoA
Succinyl-CoA
Glycine
NAD
CO2
NADH
NADH
CO2
+
+
NAD
+
CoA-SH
α-Ketoglutarate
dehydrogenase
Glutamine
Glutamate
dehydrogenase
or
Aminotransferase
α-Ketoglutarate
Proline
Carbamoyl
phophate
Pi
Citrulline
Citrulline
NH4
Glutamate
Heme
Histidine
Glutamine
synthetase
Succinate
Carbamoyl
phosphate
synthetase I
Isocitrate
FAD
Glutaminase
Tyrosine
Phenylalanine
Ornithine
NH4
Ornithine
Urea
Fumarate
Glutamine
Arginine
Notes:
Only regulatory enzymes are shown.
Red enzyme name and arrow = predominantly catabolic process
Blue enzyme name and arrow = predominantly anabolic process
Green compound name = branch-point compound
Blue compound name = amino acid or ammonium
Aspartate
Argininosuccinate
Hormone
Major Metabolic Control Hormones
Second
Receptor
Mechanism
messenger
Insulin (51 amino
Tyrosine
acid heterodimeric
kinase
peptide)
Phosphorylated
proteins
Target tissues
Liver, muscle,
adipose, pancreas,
many others
∆ Enzyme activity
Gene transcription
decreased cAMP
∆ Enzyme activity
Glucagon (29
amino acid
peptide)
G-protein
coupled
Cortisol (steroid)
Transcription Altered level of
factor
specific mRNA
Epinephrine
(tyrosine
derivative)
G-protein
coupled (at
least four
types)
cAMP
Growth
hormone (191
amino acid
protein)
Cytokine
family cell
surface
Tyrosine kinase
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cAMP
decreased cAMP
Sometimes gene
transcription
Liver, pancreas
Gene transcription
Nearly all
∆ Enzyme activity
Liver, muscle,
adipose, brain,
pancreas,
cardiovascular
PI hydrolysis
∆ Enzyme activity
Liver, muscle,
adipose; others
mediated by IGF-I
Sometimes gene
transcription
PI hydrolysis
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Regulation of Liver Metabolism
Pathway
Regulatory enzyme Stimulators
Glycolysis
Glucokinase
[glucose]
Phosphofructokinase
Fructose 2,6bisphosphate,
AMP
AMP, Fructose1,6-bisphosphate
Pyruvate kinase
Gluconeogenesis
Glycogen
synthesis
Glycogen
breakdown
Hexose monophosphate
Urea cycle
Fatty acid
synthesis
Fatty acid
breakdown
Ketone body
synthesis
Cholesterol
synthesis
Purine
synthesis
Pyrimidine
synthesis
Insulin ↑ Glucagon ↓
Epinephrine ↓ (all via
altered [F2,6bP])
Insulin ↑ Glucagon ↓
Epinephrine ↓
Glucagon ↑
Fructose 2,6bisphosphate, AMP
Insulin ↓ Glucagon ↑
Epinephrine ↑
Acetyl-CoA
ADP
Pyruvate
dehydrogenase
Citrate synthase
CoA, NAD, ADP,
pyruvate, Ca2+
NAD,
[oxaloacetate]
Isocitrate
dehydrogenase
α-ketoglutarate
dehydrogenase
Glycogen synthase
ADP, Ca2+
Acetyl-CoA, NADH,
ATP
Citrate, Long chain
acyl-CoA, ATP,
NADH, succinyl-CoA
ATP, NADH
Glycogen
phosphorylase
Glucose-6-phosphate
dehydrogenase
Glutamate
dehydrogenase
Carbamoyl phosphate
synthetase I
Acetyl-CoA
carboxylase
Carnitine acyl
transferase I
HMG-CoA synthase
Ca2+
Glucose-6phosphate
AMP
Hormones
affecting enzyme
activity
Citrate, ketone
bodies, ATP,
phosphoenolpyruvate
ATP, alanine
Phosphoenolpyruvate
carboxykinase
Fructose 1,6bisphosphatase
Glucose-6phosphatase
Pyruvate carboxylase
TCA Cycle
Inhibitors
ATP, NADH,
succinyl-CoA, GTP
Glycogen
NADP
Glucose-6-phosphate,
ATP
NADPH
ADP
ATP, GTP, NADH
N-acetylglutamate
[substrate]
Citrate
Long-chain acyl-CoA
AMP
Malonyl-CoA
Ribose-phosphate
pyrophosphokinase
PRPP glutamyl
PRPP
amidotransferase
Carbamoyl phosphate ATP, PRPP
synthetase II
Aspartate
transcarbamoylase
Insulin ↑
Cortisol ↓
Insulin ↓
Cortisol ↑
Glucagon ↑
Insulin ↓
Cortisol ↑
Insulin ↓
Cortisol ↑
Insulin ↓
Cortisol ↑
Glucagon ↑
Insulin ↑
Insulin ↑ Glucagon ↓
Epinephrine ↓
Insulin ↓ Glucagon ↑
Epinephrine ↑
Insulin ↑
Cortisol ↑
Insulin ↑
Insulin ↑ Glucagon ↓
Insulin ↑
Glucagon ↑
Acetyl-CoA
HMG-CoA reductase
Hormones
affecting
enzyme
levels
Insulin ↑
Cortisol ↓
Insulin ↑
Cortisol ↓
Cholesterol, bile
acids
Adenine, Guanine
and Thymine
nucleotides
Adenine and
Guanine nucleotides
Uridine nucleotides,
GTP
CTP
Insulin ↑ Glucagon ↓
Regulation of Skeletal Muscle Metabolism
Pathway
Glycolysis
Regulatory
enzyme
Glucose transporter
(GLUT 4)
Hexokinase
Phosphofructokinase
Glycogen
synthesis
Glycogen synthase
Glycogen
breakdown
Protein
synthesis
Glycogen
Phosphorylase
Transcription and
translation
initiation
Protein
breakdown
Protease activation
Stimulators
Inhibitors
(Muscle
contraction)
Fructose 2,6bisphosphate,
AMP, (Muscle
contraction)
Glucose-6phosphate, low
Glycogen levels
Ca2+, AMP
Hormones
affecting enzyme
activity
Insulin ↑
Cortisol ↓ (change
amount in plasma
membrane)
Glucose-6-phosphate
Citrate, ketone
bodies, ATP
Hormones
affecting
enzyme levels
Insulin ↓
Cortisol ↑
Cortisol ↓
Ca2+, AMP
Insulin ↑
Epinephrine ↓
Glucose-6-phosphate,
ATP
Insulin ↓
Epinephrine ↑
Insulin ↑
Insulin ↑
Growth
hormone
↑ Androgens
↑ Cortisol ↓
Insulin ↓
Cortisol ↑
Regulation of Adipose Tissue Metabolism
Pathway
Glycolysis
Regulatory
enzyme
Glucose transporter
(GLUT 4)
Hexokinase
Phosphofructokinase
Triacylglycerol
synthesis
Triacylglycerol
breakdown
Lipoprotein lipase
Glycerol phosphate
acyltransferase
Hormone-sensitive
lipase
Stimulators
Fructose 2,6bisphosphate,
AMP
(high VLDL,
chylomicrons)
Inhibitors
Hormones
affecting enzyme
activity
Insulin ↑
Cortisol ↓ (change
amount in plasma
membrane)
Glucose-6-phosphate
Citrate, ketone
bodies, ATP
Hormones
affecting
enzyme levels
Insulin ↓
Cortisol ↑
Cortisol ↓
Insulin ↑
(low glycerol
phosphate levels)
Insulin ↓
Epinephrine ↑
Insulin ↓
Cortisol ↑
Diabetes Mellitus: Type I
Insulin-dependent diabetes mellitus (IDDM)
“Juvenile-onset” diabetes
Diabetic Ketoacidosis (DKA)
Frequent urination (Polyuria) – Osmotic diuresis
Extreme thirst (Polydipsia)
Extreme hunger (Polyphagia)
Peripheral neuropathy
Weakness
Kussmaul respiration
Vision alterations
Ketonemia
Lipid breakdown
Protein breakdown
Lack of Insulin
Metabolic acidosis
Tissue hypoxia
Insulin resistance
Peripheral circulatory failure
Elevated glucocorticoids
Coma and Death
120
Too Much Insulin
110
100
90
5 mM
80
70
Counterregulation
60
Autonomic symptoms
50
Altered brain function
40
Lethargy
30
Coma
20
Convulsions
Permanent damage
10
0
Death
Decreased
glucose
uptake
Gluconeogenesis
Aminoacidemia
Lactic acidemia
Glycogen breakdown
Dehydration
Hyperglycemia
Osmotic diuresis
Water
and
electrolyte
loss
Loss of potassium
Diabetes Mellitus: Type II
Non-insulin-dependent diabetes mellitus (NIDDM)
“Adult-onset” diabetes
Hyperglycemic HyperOsmotic Non-Ketotic Coma
(HONK)
Oral Antihyperglycemic Drugs
O
R
NH
O
S NH C NH R
O
H3C
H2N
Sulfonylurea
NH CH3
C NH C N
CH3
Biguanide
(metformin)
S
N
O
O
Thiazolidinedione
(pioglitazone)
NH
O
Fatty Acid and Related Lipid Nomenclature and Properties
O
C1
OH
H3C
18
18 CH3
O
9
C1
10
O
OH
9
Stearic acid (18:0)
C1
10
Oleic acid (18:1 ∆9)
13
12
OH
Linoleic acid (18:2 ∆9,12)
ω9 fatty acid
ω6 fatty acid
18
H3C
Number
of
Name
Carbons
Lauric acid
12
(dodecanoic acid)
14
Myristic acid
16
Palmitic acid
18
Stearic acid
Symbol
Structure
Melting
Point
(°C)
12:0
CH3(CH2)10COOH
44
14:0
16:0
18:0
CH3(CH2)12COOH
CH3(CH2)16COOH
53
63
70
CH3(CH2)14COOH
16
Palmitoleic acid
16:1∆9
CH3(CH2)5CH=CH(CH2)7COOH
–0.5
18
Oleic acid
18:1∆9
CH3(CH2)7CH=CH(CH2)7COOH
13
18
Linoleic acid
18:2∆9,12
–5
18
α-Linolenic acid
18:3∆9,12,15
–11
18
γ-Linolenic acid
Arachidonic acid
18:3∆6,9,12
–11
20:4∆5,8,11,14
–50
20
O
Glycerol
CH2 CH CH2
OH OH OH
Triacylglycerol
O
C
CH2 CH CH2
O
C
O
O
C
O
Membrane Lipids
Phosphatidylcholine
Phosphatidyl
inositol
Phosphatidylserine
O
O
CH3
O P O CH2 CH2 N CH3
O
O
CH3
O
C
O
O
O
C
O
O
O
OH
OH
O P O
O
CH2 CH CH2
C
O
NH3
O
CH2 CH CH2
OH
OH
O
O C
O P O CH2 CH
OH
CH2 CH CH2
C
O
O
C
O
O
CH3
O P O CH2 CH2 N CH3
O
CH3
CH2 CH CH2
O
C
Ether phosphatidylcholine
(1-alkyl, 2-acyl phosphatidylcholine)
O
O
Cerebroside
Sphingomyelin
OH
O
Sphingosine
Ceramide
OH
CH3
O P O CH2 CH2 N CH3
O
OH
OH
O
CH3
O
OH
CH2 OH
NH3
HO
HO
NH
C
O
HO
NH
C
O
HO
NH
C
O
C
O