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Biosynthesis of Porphyrins

1. Porphyrins are complex organic compounds composed of four modified pyrrole subunits linked by methylene bridges. They are synthesized partly in the mitochondrion and cytosol of cells like erythrocytes and hepatic cells. 2. Biosynthesis of porphyrins involves several steps starting with the formation of δ-aminolevulinic acid from glycine and succinyl-CoA, which then combines to form porphobilinogen and other intermediates culminating in protoporphyrin IX. 3. Protoporphyrin IX then combines with ferrous iron to form heme, with its main role being to support aerobic life. Porphyrins also have

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301 views15 pages

Biosynthesis of Porphyrins

1. Porphyrins are complex organic compounds composed of four modified pyrrole subunits linked by methylene bridges. They are synthesized partly in the mitochondrion and cytosol of cells like erythrocytes and hepatic cells. 2. Biosynthesis of porphyrins involves several steps starting with the formation of δ-aminolevulinic acid from glycine and succinyl-CoA, which then combines to form porphobilinogen and other intermediates culminating in protoporphyrin IX. 3. Protoporphyrin IX then combines with ferrous iron to form heme, with its main role being to support aerobic life. Porphyrins also have

Uploaded by

Shafaqat Ghani Shafaqat Ghani
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© © All Rights Reserved
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BIOSYNTHESIS OF PORPHYRINS

and heme

Mahpara Gondal
Pharm-D
MS Pharmaceutical Chemistry

Rashid Latif College of Pharmacy


 The porphyrins are complex structures consisting of 4
pyrrole rings, united by “methyne” bridges The nitrogen
of 4 pyrrole rings can form complex with metallic ions such
as Fe++ and Mg++.

Porphyrin
 Porphyrins are a group of heterocyclic 
organic compounds, composed of four modified pyrrole
 subunits interconnected at their carbon atoms via 
methene bridges (=CH−). 

Cont…
.
Porphyrinsare synthesised partly in the
mitochondrion and partly in cytosol of
aerobic cells like developing
erythrocytes and hepatic cells.

Stages of Biosynthesis
Synthesis of porphyrins can be divided
into severel steps for understanding.

BIOSYNTHESIS OF PORPHYRINS
  1.Formation of δ-aminolevulinic acid  by the
reaction of the amino acid glycine with succinyl
-CoA from the citric acid cycle. 

 2.Two molecules of dALA are then combined by 


porphobilinogen synthase to give 
porphobilinogen (PBG), which contains a pyrrole
ring.

 3.Four PBGs are then combined through


deamination into hydroxymethyl bilane (HMB)

Cont…
4. HMB, which is hydrolysed to form the
circular tetrapyrrole uroporphyrinogen III
in the presence of uroporphyrinogen III
synthetase.

5. uroporphyrinogen III undergoes in the


reaction of decarboxylation and form
coproporphyrinogen III in the presence of
uroporphyrinogen III decarboxylase.

Cont…
6. Coproporphyrinogen III then oxidize
into protoporphyrinogen III in the
presence of coproporphyrinogen III
oxidase.

7. Then protoporphyrinogen III again


oxidize and form protoporphyrin IX in the
presence of protoporphyrin III oxidase.

Cont…
8. Protoporphyrin IX combine with ferrous
in the presence of enzyme heme
sythetase also called ferrochelatase to
form heme compound.

Cont…
Applications

The main role of porphyrins is their support of aerobic


life.

Porphyrins have been evaluated in the context of 


photodynamic therapy since they strongly absorb light,
which is then converted to energy and heat in the
illuminated areas.

Metalloporphyrin complexes are widely studied as


catalysts for the oxidation of organic compounds

Applications
Uroporphyrins- these are excreted in
negligible amounts averaging 15 to 30
ug/day.

Coproporphyrins-100 to 300ug/day are


excreted. Their excretion is increased in
lead poisoning, liver disease, and
hemolytic anemia.

Excretion of porphyrins in urine


400-1000ug/day of coproporphyrin is
excreted in feces.
An increased fecal excretion occurs in
hemolytic anemia.
A decreased excretion occurs in liver
disease.

Excretion of porphyrins in feces


The porphyrias are a group of disorders
due to abnormalities in the pathway of
biosynthesis of heme.
They can be genetic and or acquired.
Drugs include barbiturtes, sulfonamides
and sex hormones.

Porphyrias

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