PORPHYRINS

dr. Winarsi
Porphyrins are cyclic compounds formed by the linkage of
4 pyrrole rings through methylene bridges.
A characteristic property of the pophyrins is the formation of
complexes with metal ions bound to the nitrogen atom of the
pyrrole rings; example is iron porphyrin such as heme of
hemoglobin.

In nature, the metalloporphyrins are conyugated to protein to

form a number of compounds of importance in biologic
processes, include the following:
Hemoglobins: iron porphyrins attached to the protein,
globin. These conjugated proteins have the ability to combine
reversibly with oxygen, and serve as the transport mechanism
for oxygen within the blood.
Myoglobins: iron porphyrins attached to the protein, globin
and like hemoglobin, able to combine reversibly with oxygen.
They serve as respiratory pigments which occur in the muscle
cells.
 Cytochromes: Compounds which act as
electron transfer agents in oxidation-
reduction reactions. Some type of
cytochrome serve as an enzyme for
hydroxylation reaction.
 Catalases and peroxidases: Iron porphyrin
enzymes.
 Tryptophan pyrrolase: oxidation of
tryptophan.
Biosynthesis of porphyrins
Succinyl-CoA + glycine  delta
aminolevulinic acid (Amlev/ALA) 
Porphobilinogen    uroporphyrinogen
III  coproporphyrinogen III 
protoporphyrinogen III  protoporphyrin III 
heme (ferro protoporphyrin III). The
regulatory enzyme is ALA synthase, requiring
vitamin B6 as coenzyme. The terminal
enzyme heme synthesis is ferrochelatase.
The various porphyrins are all colored and
has Soret band (A characteristic absorption
spectrum near 400 nm of wavelength).
When porphyrins dissolved in strong mineral
acids or in organic solvents are illuminated
by ultraviolet light, they emit a strong red
fluorescence.
The various porphyrinogens are colorless,
whereas the various porphyrins are all colored.
Catabolism of heme: formation of bile pigment
(bilirubin).
Heme  Fe (ferro ions) + biliverdin  bilirubin
I/indirect  liver  bilirubin II/direct  blood
and bile  gallbladder  intestine 
urobilinogen/stercobilinogen 
urobilin(urine)/stercobilin(feces).
Urobilinogen undergoes enterohepatic
circulation, and some of it is excreted in the
urine.
E: UDP-GLUCUROSYL TRANSFERASE
Bilirubin I + 2 UDP-glucuronic acids 
bilirubin diglucuronide (bilirubin II) + 2 UDP.
Bilirubin I/ unconyugated bilirubin: bilirubin
II/conyugated bilirubin.

Neonatal ‘Physiologic Jaundice’

(unconyugated hyperbilirubinemia).
SEKIAN