Chemical Structure
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 |
When leaves degreen in the process of plant senescence, chlorophyll is converted to a group of colourless tetrapyrroles known as nonfluorescent chlorophyll catabolites (NCC's) with the general structure:
These compounds have also been identified in several ripening fruits.
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