Pyrrole Pigments

Chlorophyll and Haemoglobin are important

natural porphyrins

Contain the Porphin skeleton

Contain 4 Pyrrole Rings linked through and
by 4 methine bridges.

'

N
HN

NH
N

Porphin does not exist in nature

Biosynthetic studies show:

All N come from Glycine

One -C in each pyrrole ring and each of the 4
bridging C come from methylene of Glycine

All remaining C come from Succinate

(derived from Acetate in TCA Cycle)

'

CO2H
NH2
Glycine

NH

HN

Porphobilinogen is the common precursor to porphyrins

C3 Propionate

C2 Acetate

HO2C

H2N

N
H

CO2H

N
H

H2N

Derived from 2 molecules of -amino laevulinic acid (ALA)

H2N

N
H

CO2H

CO2H

O
O
H2 N

H2N

- H2O

CO2H

CO2H
O

N
H2N

CO2H

CO2H
O
H
N
H2N

CO2H

CO2H
O

H2N

N
H
- H2O

CO2H

CO2H

H
N
H2 N

H2N

N
H

CO2H

O
H2N
-ALA comes from condensation of succinyl CoA and
Glycine Pyridoxal

CO2H
N

CO2H

CH

+
OH

H3C

OP
N

O
SCoA

CO2H

O
HOOC

CH
NH2
-CO2

CO2H

O
CH2
H2N

From Glycine

H2N

N
H

All N come from Glycine

One -C in each pyrrole ring and each of the 4 bridging C come from
methylene of Glycine
All remaining C come from Succinate
(derived from Acetate in TCA Cycle)

4 of the Pyrroles combine to give Bilane

H2N

N
H

H2N

- NH3

N
H

H2N

N
H

N
H

2
H2 N

N
H

N
H
- NH3

H2N

N
H

N
H

N
H

N
H

A
NH
H2N
NH

P
HN

HN

A
A

P
Bilane

A
NH
H2N
NH

P
HN

HN

A
A

A
NH

H
N

P
HN

HN
A

A
NH

H
N

P
HN

HN
A

A
NH

H
N

P
HN

HN
A

Same as:

A
NH

NH

P
HN

HN

A
P

A
NH

NH

P
HN

HN

A
P

A
NH

NH

P
HN

HN

A
P

A
NH

NH

P
HN

HN

A
P

H
P

A
NH

NH

P
HN

HN

A
P

Uroporphyrinogen III

- 4 CO2
P

CH3

H3C
NH

NH

P
HN

HN

H3C

CH3
P

- 2 CO2
-4 H

CH3
H3C
NH

NH

HN

HN

H3C

CH3
P

-6 H

CH3
H3C
N

HN

NH

H3C

CH3
P

CH3
H3C
N

HN

NH

H3C

Protoporphyrin IX

CH3

CO2H

CO2H

CH3
H3C
N

N
Fe

N
H3C

Heme

N
CH3

CO2H

CO2H

CH3
CH3

H3C
N

N
Mg

H3C

CH3

H3CO2C
CO2H

Chlorophyll

Vitamin B12