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Histidine decarboxylase
CO2
H N
Histidine
Histamine
Histamine: Synthesized in and released by mast cells Mediator of allergic response: vasodilation, bronchoconstriction (H1 receptors) H1 blockers: Diphenhydramine (Benadryl) Loratidine (Claritin) Stimulates secretion of gastric acid (H2 receptors)
Polyamine Biosynthesis
+ H3 NCH2 CH2 CH2 CHCO 2 Ornithine (from urea cycle)
NH3+
+ H3N
Putrescine
+ NH3
CO2
Decarboxylated SAM
Spermidine synthase Spermine synthase
+ H3N
H + H3N H + N H + N H
5-Methylthioadenosine Decarboxylated SAM
+ NH3
5-Methylthioadenosine
H +N H + NH3
Spermine
Spermidine
Trp hydroxylase HO
N H
CH2CH2NH2 HO
Decarboxylase
O2
Tryptophan (Trp)
5-Hydroxytryptophan
N H
N H
CO2
Serotonin
Serotonin formed in:
Brain (neurotransmitter; regulation of sleep, mood, appetite) Platelets (platelet aggregation, vasoconstriction) Smooth muscle (contraction) Gastrointestinal tract (enterochromaffin cells - major storage site)
MAO
HO N H
Serotonin
Dehydrogenase
CH2CO2H HO
N H
2 Steps
N H
Serotonin
Melatonin
Melatonin: Formed principally in pineal gland Synthesis controlled by light, among other factors Induces skin lightening Suppresses ovarian function Possible use in sleep disorders
Melanin Formation
HO NH3+ CH2CHCO2-
Tyrosinase
HO NH3+ HO CH2CHCO2-
Tyrosine
DOPA Tyrosinase
O
Melanin formed in skin (melanocytes), eyes, and hair In skin, protects against sunlight Albinism: genetic deficiency of tyrosinase
Dopaquinone
Catecholamine Biosynthesis
HO NH3+ CH2CHCO2Tyr hydroxylase
HO
Catechol
NH3+
O2
HO
CH2CHCO2-
Tyrosine
HO
Epinephrine (Adrenaline)
CHCH2NHCH3 OH
S-Adenosylhomocysteine SAM Methyl transferase
CO2
HO
HO
HO
CH2CH2NH2
Dopamine
HO CHCH2 NH2 OH
Norepinephrine
GABA Formation
NH3+
-
Glutamate decarboxylase
NH3+
-
CO2
GABA is an important inhibitory neurotransmitter in the brain Drugs (e.g., benzodiazepines) that enhance the effects of GABA are useful in treating epilepsy
+ H2 N=C-HNCH2 CO 2 Guanidoacetate
SAM + ATP
NH2
Arginine
H N
Glycine
Ornithine
Creatinine (Urine)
HN N CH3
S-Adenosylhomocysteine + ADP
Creatine
+ H2 N=C-NCH2 CO 2 CH3
Phosphocreatine
NHPO3-2
ATP
ADP + Pi