Chlorophyll is a chlorin pigment,
which is structurally similar to and produced through the same metabolic
pathway as other porphyrin pigments such as heme. At the center of the chlorin
ring is a magnesium ion. At the time of its discovery in the early 1900s, this
was the first time that this element had been detected in living tissue. For
the structures depicted in this article, some of the ligands attached to the Mg2+
center are omitted for clarity. The chlorin ring can have several different
side chains, usually including a long phytol chain. There are a few different
forms that occur naturally, but the most widely distributed form in terrestrial
plants is chlorophyll a. After initial work done by German chemist Richard Willstätter spanning from 1905 to 1915, the general
structure of chlorophyll a was elucidated by Hans Fischer in 1940. By 1960, when most of the
stereochemistry of chlorophyll a was known, Robert Burns Woodward
published a total synthesis of the molecule. In 1967, the last remaining
stereochemical elucidation was completed by Ian Fleming, and in 1990 Woodward
and co-authors published an updated synthesis. Chlorophyll f was announced to
be present in cyanobacteria and other oxygenic microorganisms that form stromatolites
in 2010; a molecular formula of C55H70O6N4Mg
and a structure of (2-formyl)-chlorophyll a were deduced based on NMR,
optical and mass spectra. The different structures of chlorophyll are
summarized below:
Chlorophyll a
|
Chlorophyll b
|
Chlorophyll c1
|
Chlorophyll c2
|
Chlorophyll d
|
Chlorophyll f
|
|
Molecular
formula
|
C55H72O5N4Mg
|
C55H70O6N4Mg
|
C35H30O5N4Mg
|
C35H28O5N4Mg
|
C54H70O6N4Mg
|
C55H70O6N4Mg
|
C2 group
|
-CH3
|
-CH3
|
-CH3
|
-CH3
|
-CH3
|
-CHO
|
C3 group
|
-CH=CH2
|
-CH=CH2
|
-CH=CH2
|
-CH=CH2
|
-CHO
|
-CH=CH2
|
C7 group
|
-CH3
|
-CHO
|
-CH3
|
-CH3
|
-CH3
|
-CH3
|
C8 group
|
-CH2CH3
|
-CH2CH3
|
-CH2CH3
|
-CH=CH2
|
-CH2CH3
|
-CH2CH3
|
C17 group
|
-CH2CH2COO-Phytyl
|
-CH2CH2COO-Phytyl
|
-CH=CHCOOH
|
-CH=CHCOOH
|
-CH2CH2COO-Phytyl
|
-CH2CH2COO-Phytyl
|
C17-C18 bond
|
Single
(chlorin) |
Single
(chlorin) |
Double
(porphyrin) |
Double
(porphyrin) |
Single
(chlorin) |
Single
(chlorin) |
Occurrence
|
Universal
|
Mostly plants
|
Various algae
|
Various algae
|
Cyanobacteria
|
Cyanobacteria
|
Structure of chlorophyll a |
Structure of chlorophyll b |
Structure of chlorophyll d |
These compounds have also been
identified in several ripening fruits.
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