This document summarizes aromatic amino acid metabolism. The three aromatic amino acids are phenylalanine, tyrosine, and tryptophan. Phenylalanine is converted to tyrosine via phenylalanine hydroxylase. Tyrosine can be used to produce melanin, dopamine, norepinephrine, epinephrine, and thyroxine. Tryptophan breakdown occurs via the kynurenine pathway or serotonin pathway to produce NAD+, serotonin, and melatonin. Albinism is discussed as arising from defects in tyrosine metabolism that reduce melanin production.
Catabolism of Phenylalanine and Tyrosine | Disorders Of Tyrosine Metabolismkiransharma204
This PPT contains topic related to Catabolism of Phenylalanine and Tyrosine, Disorders Of Tyrosine Metabolism and metabolic disorders like Phenyketonuria, Albinism, Alkaptonuria and Tyrosinemia.
Books referred: https://www.amazon.in/s?k=satyanarayan+biochemistry&i=stripbooks&crid=2UMKA76J0R8WC&sprefix=satya%2Cstripbooks%2C456&ref=nb_sb_ss_i_2_5
introduction of Phenylalanine and Tyrosine , structures and metabolic fate of phenylalaine and tyrosine . different end product of Tyrosine ,: melanin and its types , epinephrine and norepinephrine, thyroide hormopne , different inheritance disease, PKU, Tyrosinemia type I, II & III, Albinism, Alkaptouria
catabolism of tyrosine
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2. • Aromatic amino acid contains aromatic ring .
• They are-
• Phenylalanine(Benzene ring or phenyl)
• Tyrosine(phenol)
• Tryptophane(indole)
3. phenylalanine
• Essential amino acid
• Partially glucogenic and partially ketogenic.
• The only function of phenylalanine is its
conversion to tyrosine.
• For this reason ingestion of tyrosine can
reduce the dietary requirement of
phenylalanine.tjis phenomenon known as
“spring action” of tyrosine on phenylalanine.
4. Conversion of phenylalanine to
tyrosine
• The degradation of phenylalanine mostly
occurs through tyrosine.
• The reaction involves addition of a hydroxyl
group to the aromatic ring.
• It needs NADPH,NADH,and tetra
hydrobiopterin as co-enzyme.
• This is an irreversible reaction and tyrosine
cannot replenish phenylalanine.
7. • The metabolism of phenylalanine and tyrosine
is considered together.
• As phenylalanine is converted to tyrosine a
single pathway is responsible for the
degradation of both these amino acids,which
mostly occurs in liver.
• Tyr first undergoes transamination to give P-
hydroxyphenylpyruvate. this reaction is
catalysed by tyrosine transaminase.
8. • P-hydroxyphenylpyruvate
hydroxylase(dioxygenase)is a copper
containing enzyme.
• It catalyses oxidative decarboxylation as well
as hydroxylation of phenyl ring to produce
HOMOGENTISATE.
• A shifting of OH group from Para to meta
position occur,and incorporates a new
hydroxyl group at para position.
9. • This reaction requires ascorbic acid.
• HOMOGENTISATE OXIDASE cleaves the
bengene ring of homogentisate to form 4-
maleylacetoacetate.
• Maleylacetoacetate isomarised to form 4-
fumaryl acetoacetate and this reaction is
catalysed by maleylacetoacetate isomarase.
10. • maleyl acetoacetate is get converted into
fumaryl acetoacetate with the help of
fumarylacetoacetase.
• Fumaryl acetoacetate hydrolysed in to
fumarate and acetoacetate with the help of
enzyme fumarylacetoacetase.
11. SYNTHESIS OF MELANINE
• It is pigment of skin,hair and eyes.
• Tyrosine is the precursor of melanine.
• Tyrosinase enzyme required for its synthesis.
• Tyrosinase hydroxylas tyrosine to form 3,4-
dihydroxyphenylalanine(DOPA).
• Dopa is converted to dopaquinone.
• A subsequent couple of reaction occurs.
• Formation of leucodopachromeand indole 5-6 –
quinone.
13. • Another pathway from dopaquinone is als
identified.
• Cysteine condenses with dopaquinone and
series of reactions results in synthesis of red
melanines
14. • Tyrosine is also required for thyroid hormone
and catecholamine synthesis.
• Tyrosine is precursor for the synthesis of
dopamine,norepinephrine and epinephrine.
• For the formation of dopa the enzyme
required is TYROSINE HYDROXYLASE.
15. Melanin synthesis
• Melanin is black pigment of skin, hair & eyes
• Synthesis occurs in melanosomes present in
melanocytes.
• Tyrosine is the precursor of melanin and
tyrosinase is the enzyme involved in it’s
formation
• Melanochromes formed from tyrosine
polymerizes to form melanin polymers
16. Melanin, a color pigment
• Skin color is determined by the relative
concentrations of black & red melanins
• This is dependent on genetic and environmental
factors
• Formation of moles is due to hyperpigmentation
caused by the hyperactivity of melanocytes and
formation of white patches is due to localized absence
or degeneration of melanoytes from the skin.
• Albinism is an inborn error with generalized lack of
melanin synthesis
19. What is albinism?
Albinism is a group of genetic conditions that causes a
lack of pigment. It can effect only the eyes or both the
eyes and skin. Most types of albinism are inherited when
an individual receives the albinism gene from both
parents. The exception is one type of ocular albinism,
which is passed on from mothers to their sons.
20. Description
• Due to the defect in tyrosine metabolism it results in
a deficiency of melanin production and partial or full
absence of pigment from the skin, hair, and eyes
• It may be inherited by one of several modes:
autosomal recessive, autosomal dominant, or
Complete albinism
• Affected people may appear to have white hair, skin
& iris color. They may have vision defects and
photophobia.
• Oculocutaneous albinism is most severe form
resulting from a deficiency of tyrosinase
activity, causing a total absence of pigment from the
hair, eyes & skin
22. Symptoms
• Absence of pigment from the hair, skin, or iris of
eyes
• Lighter than normal skin and hair or complete
albinism
• Most forms of complete albinism have some of the
following possible symptoms:
– Rapid eye movements
– Strabismus (eyes not tracking properly)
– Photophobia (avoidance of light because of discomfort)
– Decreased visual acuity
– Functional blindness
23. Causes
• Albinism is caused by an alteration of the
gene that regulates the melanin pigment
synthesis.
30. TRYPTOPHAN
• Essential aminoacid.
• Contains an indole ring.
• It’s a alpha amino beta indole propionic acid.
• Tryptophane is both glucogenic and ketogenic.
• It is precursor of NAD+ and NADP+ serotonin
and melatonin.
32. KYNURENINE PATHWAY
• Mostly occurs in liver.
• Tryptophan converted in to N-
formylkynurenine with the help of enzyme
tryptophan pyrrolase.
• Formamidase hydrolases formyl kynurenine
and liberates formate and kynurenine.
• Kynurenine undergose NADPH-dependent
hydroxylation to give 3-hydroxykynurenine.
33. • Kynureninase, a pyridoxal phosphate dependent
enzyme acts on the 3-hydroxy kynurenine and
splits off alanine.
• Due to the lack of PLP kynureninase reaction is
blocked and 3-hydroxy kynurenine is diverted to
form xenthurenate, serves as an indication of
vitamin B6 deficiency.
• 3-hydroxy anthranilate is cleaved by an oxidase to
form an unstable intermediate 2-amino 3carboxy
muconate semialdehyde.
34. • This compound has 3 fates-
• 1-Spontaneous cyclization to form quinolinate
for NAD+ synthesis.
• 2-To produce picolinate.
• 3-To produce 2-aminomuconate for acetyl
CO.A synthesis.
35. • Tryptophan is also produces indole acetate.
• Tryptophan is not precursor for the synthesis
of niacin.
• Quinolinate under gose decarboxylation and
form nicotinate mononucleotide by the
enzyme quinolinate phosphoribosyl
transferase.
36. SEROTONIN PATHWAY
• It is a neurutransmitter, syntheseized from
tryptophan.
• Only 1% of tryptophan is converted in to
serotonin.
• The production of 5HT occurs in the target
tissues.
37.
38. Synthesis of serotonin
• Synthesized in the intestinal cells.
• Tryptophane is first hydroxylated at 5th carbon
by tryptophane hydroxylase.
• This enzyme requires tetrahydrobiopterin as a
co factor.
• 5-hydroxytryptophane is decarboxylated by
aromatic amino acid decarboxylase to give
serotonin.
39. Degradation and functions of
serotonin
• Monoamine oxidase degrades serotonin to 5-
hydroxy indole acetate which is excreted in
urine.
• Functions-
• 1-as a powerful VASOCONSTRICTOR.
• 2-involves in regulation of cerebral activity.
• 3-controls beheviourals patterns,sleep,blood
pressure and body temprature.
40. • 4-evokes the release of peptide hormones.
• 5-also necessary for the motility of GIT.
