Chlorophyll a

Last updated
Chlorophyll a
Chlorophyll a.svg
Names
IUPAC name
Chlorophyll a
Systematic IUPAC name
Magnesium [methyl (3S,4S,21R)-14-ethyl-4,8,13,18-tetramethyl-20-oxo-3-(3-oxo-3-{[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]oxy}propyl)-9-vinyl-21-phorbinecarboxylatato(2−)-κ2N,N′]
Other names
α-Chlorophyll
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.852 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-536-6
PubChem CID
RTECS number
  • FW6420000
UNII
  • InChI=1S/C55H73N4O5.Mg/c1-13-39-35(8)42-28-44-37(10)41(24-25-48(60)64-27-26-34(7)23-17-22-33(6)21-16-20-32(5)19-15-18-31(3)4)52(58-44)50-51(55(62)63-12)54(61)49-38(11)45(59-53(49)50)30-47-40(14-2)36(9)43(57-47)29-46(39)56-42;/h13,26,28-33,37,41,51H,1,14-25,27H2,2-12H3,(H-,56,57,58,59,61);/q-1;+2/p-1/b34-26+;/t32-,33-,37+,41+,51-;/m1./s1 Yes check.svgY
    Key: ATNHDLDRLWWWCB-AENOIHSZSA-M Yes check.svgY
  • InChI=1S/C55H73N4O5.Mg/c1-13-39-35(8)42-28-44-37(10)41(24-25-48(60)64-27-26-34(7)23-17-22-33(6)21-16-20-32(5)19-15-18-31(3)4)52(58-44)50-51(55(62)63-12)54(61)49-38(11)45(59-53(49)50)30-47-40(14-2)36(9)43(57-47)29-46(39)56-42;/h13,26,28-33,37,41,51H,1,14-25,27H2,2-12H3,(H-,56,57,58,59,61);/q-1;+2/p-1/b34-26+;/t32?,33?,37-,41-,51+;/m0./s1
    Key: ATNHDLDRLWWWCB-WJQLOWBJSA-M
  • CCC1=C(C2=NC1=CC3=C(C4=C([N-]3)C(=C5[C@H]([C@@H](C(=N5)C=C6C(=C(C(=C2)[N-]6)C=C)C)C)CCC(=O)OC/C=C(\C)/CCCC(C)CCCC(C)CCCC(C)C)[C@H](C4=O)C(=O)OC)C)C.[Mg+2]
  • COC(=O)C9C(=O)c6c(C)c3N7c6c9c2C(CCC(=O)COCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C(C)c1cc5N8c(cc4n([Mg]78n12)c(c=3)c(CC)c4c)c(C=C)c5C
Properties
C55H72MgN4O5
Molar mass 893.509 g·mol−1
AppearanceGreen
Odor Odorless
Density 1.079 g/cm3 [1]
Melting point ~152.3 °C (306.1 °F; 425.4 K) [2]
decomposes [1]
Insoluble
Solubility Very soluble in ethanol, ether
Soluble in ligroin, [2] acetone, benzene, chloroform [1]
Absorbance See text
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Chlorophyll a is a specific form of chlorophyll used in oxygenic photosynthesis. It absorbs most energy from wavelengths of violet-blue and orange-red light, and it is a poor absorber of green and near-green portions of the spectrum. [3] Chlorophyll does not reflect light but chlorophyll-containing tissues appear green because green light is diffusively reflected by structures like cell walls. [4] This photosynthetic pigment is essential for photosynthesis in eukaryotes, cyanobacteria and prochlorophytes because of its role as primary electron donor in the electron transport chain. [5] Chlorophyll a also transfers resonance energy in the antenna complex, ending in the reaction center where specific chlorophylls P680 and P700 are located. [6]

Contents

Distribution of chlorophyll a

Chlorophyll a is essential for most photosynthetic organisms to release chemical energy but is not the only pigment that can be used for photosynthesis. All oxygenic photosynthetic organisms use chlorophyll a, but differ in accessory pigments like chlorophyll b. [5] Chlorophyll a can also be found in very small quantities in the green sulfur bacteria, an anaerobic photoautotroph. [7] These organisms use bacteriochlorophyll and some chlorophyll a but do not produce oxygen. [7] Anoxygenic photosynthesis is the term applied to this process, unlike oxygenic photosynthesis where oxygen is produced during the light reactions of photosynthesis.

Molecular structure

The molecular structure of chlorophyll a consists of a chlorin ring, whose four nitrogen atoms surround a central magnesium atom, and has several other attached side chains and a hydrocarbon tail formed by a phytol ester.

Chlorophyll-a-3D-balls.png
Chlorophyll-a-3D-spacefill.png
Structure of chlorophyll a molecule showing the phytol tail

Chlorin ring

Chlorin, the central ring structure of the chlorophyll a Chlorin.svg
Chlorin, the central ring structure of the chlorophyll a

Chlorophyll a contains a magnesium ion encased in a large ring structure known as a chlorin. The chlorin ring is a heterocyclic compound derived from pyrrole. Four nitrogen atoms from the chlorin surround and bind the magnesium atom. The magnesium center uniquely defines the structure as a chlorophyll molecule. [8] The porphyrin ring of bacteriochlorophyll is saturated, and lacking alternation of double and single bonds causing variation in absorption of light. [9]

Side chains

The green boxed CH3 is the methyl group at the C-7 position chlorophyll a C-3 position Chlorophyll a.svg
The green boxed CH3 is the methyl group at the C-7 position chlorophyll a

Side chains are attached to the chlorin ring of the various chlorophyll molecules. Different side chains characterize each type of chlorophyll molecule, and alters the absorption spectrum of light. [10] [11] For instance, the only difference between chlorophyll a and chlorophyll b is that chlorophyll b has an aldehyde instead of a methyl group at the C-7 position. [11]

Hydrocarbon tail

The phytol ester of chlorophyll a (R in the diagram) is a long hydrophobic tail which anchors the molecule to other hydrophobic proteins in the thylakoid membrane of the chloroplast. [5] Once detached from the porphyrin ring, phytol becomes the precursor of two biomarkers, pristane and phytane, which are important in the study of geochemistry and the determination of petroleum sources. [12]

Biosynthesis

The Chlorophyll a biosynthetic pathway utilizes a variety of enzymes. [13] In most plants, chlorophyll is derived from glutamate and is synthesised along a branched pathway that is shared with heme and siroheme. [14] [15] [16] The initial steps incorporate glutamic acid into 5-aminolevulinic acid (ALA); two molecules of ALA are then reduced to porphobilinogen (PBG), and four molecules of PBG are coupled, forming protoporphyrin IX. [8]

Chlorophyll synthase [17] is the enzyme that completes the biosynthesis of chlorophyll a [18] [19] by catalysing the reaction EC 2.5.1.62

chlorophyllide a + phytyl diphosphate chlorophyll a + diphosphate

This forms an ester of the carboxylic acid group in chlorophyllide a with the 20-carbon diterpene alcohol phytol.

Reactions of photosynthesis

Absorbance of light

Light spectrum

Absorption spectrum of chlorophyll a and chlorophyll b. The use of both together enhances the size of the absorption of light for producing energy. Chlorophyll ab spectra-en.svg
Absorption spectrum of chlorophyll a and chlorophyll b. The use of both together enhances the size of the absorption of light for producing energy.

Chlorophyll a absorbs light within the violet, blue and red wavelengths. Accessory photosynthetic pigments broaden the spectrum of light absorbed, increasing the range of wavelengths that can be used in photosynthesis. [5] The addition of chlorophyll b next to chlorophyll a extends the absorption spectrum. In low light conditions, plants produce a greater ratio of chlorophyll b to chlorophyll a molecules, increasing photosynthetic yield. [10]

Light gathering

The antenna complex with energy transfer within the thylakoid membrane of a chloroplast. Chlorophyll a in the reaction center is the only pigment to pass boosted electrons to an acceptor (modified from 2). Chlorophyll a antenna complex.jpg
The antenna complex with energy transfer within the thylakoid membrane of a chloroplast. Chlorophyll a in the reaction center is the only pigment to pass boosted electrons to an acceptor (modified from 2).

Absorption of light by photosynthetic pigments converts photons into chemical energy. Light energy radiating onto the chloroplast strikes the pigments in the thylakoid membrane and excites their electrons. Since the chlorophyll a molecules only capture certain wavelengths, organisms may use accessory pigments to capture a wider range of light energy shown as the yellow circles. [6] It then transfers captured light from one pigment to the next as resonance energy, passing energy one pigment to the other until reaching the special chlorophyll a molecules in the reaction center. [10] These special chlorophyll a molecules are located in both photosystem II and photosystem I. They are known as P680 for Photosystem II and P700 for Photosystem I. [20] P680 and P700 are the primary electron donors to the electron transport chain. These two systems are different in their redox potentials for one-electron oxidation. The Em for P700 is approximately 500mV, while the Em for P680 is approximately 1,100-1,200 mV. [20]

Primary electron donation

Chlorophyll a is very important in the energy phase of photosynthesis. Two electrons need to be passed to an electron acceptor for the process of photosynthesis to proceed. [5] Within the reaction centers of both photosystems there are a pair of chlorophyll a molecules that pass electrons on to the transport chain through redox reactions. [20]

Ocean

The concentration of chlorophyll A is used as an index of phytoplankton biomass. In the ocean, phytoplankton all contain the chlorophyll pigment, which has a greenish color.

Phytoplankton are microscopic organisms that live in watery environments and changes in the amount of phytoplankton indicate the change in productivity of the ocean. Phytoplankton can be affected indirectly by climatic factors, such as changes in water temperatures and surface winds. [21]

See also

Related Research Articles

<span class="mw-page-title-main">Chlorophyll</span> Green pigments found in plants, algae and bacteria

Chlorophyll is any of several related green pigments found in cyanobacteria and in the chloroplasts of algae and plants. Its name is derived from the Greek words χλωρός, khloros and φύλλον, phyllon ("leaf"). Chlorophyll allow plants to absorb energy from light.

<span class="mw-page-title-main">Photosynthesis</span> Biological process to convert light into chemical energy

Photosynthesis is a biological process used by many cellular organisms to convert light energy into chemical energy, which is stored in organic compounds that can later be metabolized through cellular respiration to fuel the organism's activities. The term usually refers to oxygenic photosynthesis, where oxygen is produced as a byproduct and some of the chemical energy produced is stored in carbohydrate molecules such as sugars, starch, glycogen and cellulose, which are synthesized from endergonic reaction of carbon dioxide with water. Most plants, algae and cyanobacteria perform photosynthesis; such organisms are called photoautotrophs. Photosynthesis is largely responsible for producing and maintaining the oxygen content of the Earth's atmosphere, and supplies most of the biological energy necessary for complex life on Earth.

<span class="mw-page-title-main">Chlorin</span> Chemical compound

In organic chemistry, chlorins are tetrapyrrole pigments that are partially hydrogenated porphyrins. The parent chlorin is an unstable compound which undergoes air oxidation to porphine. The name chlorin derives from chlorophyll. Chlorophylls are magnesium-containing chlorins and occur as photosynthetic pigments in chloroplasts. The term "chlorin" strictly speaking refers to only compounds with the same ring oxidation state as chlorophyll.

<span class="mw-page-title-main">Thylakoid</span> Membrane enclosed compartments in chloroplasts and cyanobacteria

Thylakoids are membrane-bound compartments inside chloroplasts and cyanobacteria. They are the site of the light-dependent reactions of photosynthesis. Thylakoids consist of a thylakoid membrane surrounding a thylakoid lumen. Chloroplast thylakoids frequently form stacks of disks referred to as grana. Grana are connected by intergranal or stromal thylakoids, which join granum stacks together as a single functional compartment.

<span class="mw-page-title-main">Bacteriochlorophyll</span> Chemical compound

Bacteriochlorophylls (BChl) are photosynthetic pigments that occur in various phototrophic bacteria. They were discovered by C. B. van Niel in 1932. They are related to chlorophylls, which are the primary pigments in plants, algae, and cyanobacteria. Organisms that contain bacteriochlorophyll conduct photosynthesis to sustain their energy requirements, but the process is anoxygenic and does not produce oxygen as a byproduct. They use wavelengths of light not absorbed by plants or cyanobacteria. Replacement of Mg2+ with protons gives bacteriophaeophytin (BPh), the phaeophytin form.

<span class="mw-page-title-main">Photosystem</span> Structural units of protein involved in photosynthesis

Photosystems are functional and structural units of protein complexes involved in photosynthesis. Together they carry out the primary photochemistry of photosynthesis: the absorption of light and the transfer of energy and electrons. Photosystems are found in the thylakoid membranes of plants, algae, and cyanobacteria. These membranes are located inside the chloroplasts of plants and algae, and in the cytoplasmic membrane of photosynthetic bacteria. There are two kinds of photosystems: PSI and PSII.

<span class="mw-page-title-main">Photosystem I</span> Second protein complex in photosynthetic light reactions

Photosystem I is one of two photosystems in the photosynthetic light reactions of algae, plants, and cyanobacteria. Photosystem I is an integral membrane protein complex that uses light energy to catalyze the transfer of electrons across the thylakoid membrane from plastocyanin to ferredoxin. Ultimately, the electrons that are transferred by Photosystem I are used to produce the moderate-energy hydrogen carrier NADPH. The photon energy absorbed by Photosystem I also produces a proton-motive force that is used to generate ATP. PSI is composed of more than 110 cofactors, significantly more than Photosystem II.

<span class="mw-page-title-main">Photophosphorylation</span> Biochemical process in photosynthesis

In the process of photosynthesis, the phosphorylation of ADP to form ATP using the energy of sunlight is called photophosphorylation. Cyclic photophosphorylation occurs in both aerobic and anaerobic conditions, driven by the main primary source of energy available to living organisms, which is sunlight. All organisms produce a phosphate compound, ATP, which is the universal energy currency of life. In photophosphorylation, light energy is used to pump protons across a biological membrane, mediated by flow of electrons through an electron transport chain. This stores energy in a proton gradient. As the protons flow back through an enzyme called ATP synthase, ATP is generated from ADP and inorganic phosphate. ATP is essential in the Calvin cycle to assist in the synthesis of carbohydrates from carbon dioxide and NADPH.

P680, or photosystem II primary donor, is the reaction-center chlorophyll a molecular dimer associated with photosystem II in plants, algae, and cyanobacteria, and central to oxygenic photosynthesis.

<span class="mw-page-title-main">Chromophore</span> A molecule that absorbs light

A chromophore is a molecule which absorbs light at a particular wavelength and emits color as a result. Chromophores are commonly referred to as colored molecules for this reason. The word is derived from Ancient Greek χρῶμᾰ (chroma) 'color', and -φόρος (phoros) 'carrier of'. Many molecules in nature are chromophores, including chlorophyll, the molecule responsible for the green colors of leaves. The color that is seen by our eyes is that of the light not absorbed by the reflecting object within a certain wavelength spectrum of visible light. The chromophore indicates a region in the molecule where the energy difference between two separate molecular orbitals falls within the range of the visible spectrum. Visible light that hits the chromophore can thus be absorbed by exciting an electron from its ground state into an excited state. In biological molecules that serve to capture or detect light energy, the chromophore is the moiety that causes a conformational change in the molecule when hit by light.

Chlorophyll <i>b</i> Chemical compound

Chlorophyll b is a form of chlorophyll. Chlorophyll b helps in photosynthesis by absorbing light energy. It is more soluble than chlorophyll a in polar solvents because of its carbonyl group. Its color is green, and it primarily absorbs blue light.

Photodissociation, photolysis, photodecomposition, or photofragmentation is a chemical reaction in which molecules of a chemical compound are broken down by photons. It is defined as the interaction of one or more photons with one target molecule.

<span class="mw-page-title-main">Photosynthetic reaction centre</span> Molecular unit responsible for absorbing light in photosynthesis

A photosynthetic reaction center is a complex of several proteins, pigments, and other co-factors that together execute the primary energy conversion reactions of photosynthesis. Molecular excitations, either originating directly from sunlight or transferred as excitation energy via light-harvesting antenna systems, give rise to electron transfer reactions along the path of a series of protein-bound co-factors. These co-factors are light-absorbing molecules (also named chromophores or pigments) such as chlorophyll and pheophytin, as well as quinones. The energy of the photon is used to excite an electron of a pigment. The free energy created is then used, via a chain of nearby electron acceptors, for a transfer of hydrogen atoms (as protons and electrons) from H2O or hydrogen sulfide towards carbon dioxide, eventually producing glucose. These electron transfer steps ultimately result in the conversion of the energy of photons to chemical energy.

A light-harvesting complex consists of a number of chromophores which are complex subunit proteins that may be part of a larger super complex of a photosystem, the functional unit in photosynthesis. It is used by plants and photosynthetic bacteria to collect more of the incoming light than would be captured by the photosynthetic reaction center alone. The light which is captured by the chromophores is capable of exciting molecules from their ground state to a higher energy state, known as the excited state. This excited state does not last very long and is known to be short-lived.

P700, or photosystem I primary donor, is the reaction-center chlorophyll a molecular dimer associated with photosystem I in plants, algae, and cyanobacteria.

<span class="mw-page-title-main">Pheophytin</span> Chlorophyll molecules lacking a central Mg2+ ion

Pheophytin or phaeophytin is a chemical compound that serves as the first electron carrier intermediate in the electron transfer pathway of Photosystem II in plants, and the type II photosynthetic reaction center found in purple bacteria. In both PS II and RC P870, light drives electrons from the reaction center through pheophytin, which then passes the electrons to a quinone (QA) in RC P870 and RC P680. The overall mechanisms, roles, and purposes of the pheophytin molecules in the two transport chains are analogous to each other.

<span class="mw-page-title-main">Light-dependent reactions</span> Photosynthetic reactions

Light-dependent reactions refers to certain photochemical reactions that are involved in photosynthesis, the main process by which plants acquire energy. There are two light dependent reactions, the first occurs at photosystem II (PSII) and the second occurs at photosystem I (PSI).

<span class="mw-page-title-main">Anoxygenic photosynthesis</span> Process used by obligate anaerobes

Anoxygenic photosynthesis is a special form of photosynthesis used by some bacteria and archaea, which differs from the better known oxygenic photosynthesis in plants in the reductant used and the byproduct generated.

<span class="mw-page-title-main">Ycf9 protein domain</span> Plastid protein involved in photosynthesis

In molecular biology, the PsbZ (Ycf9) is a protein domain, which is low in molecular weight. It is a transmembrane protein and therefore is located in the thylakoid membrane of chloroplasts in cyanobacteria and plants. More specifically, it is located in Photosystem II (PSII) and in the light-harvesting complex II (LHCII). Ycf9 acts as a structural linker, that stabilises the PSII-LHCII supercomplexes. Moreover, the supercomplex fails to form in PsbZ-deficient mutants, providing further evidence to suggest Ycf9's role as a structural linker. This may be caused by a marked decrease in two LHCII antenna proteins, CP26 and CP29, found in PsbZ-deficient mutants, which result in structural changes, as well as functional modifications in PSII.

<span class="mw-page-title-main">Chlorophyllide</span> Chemical compound

Chlorophyllide a and Chlorophyllide b are the biosynthetic precursors of chlorophyll a and chlorophyll b respectively. Their propionic acid groups are converted to phytyl esters by the enzyme chlorophyll synthase in the final step of the pathway. Thus the main interest in these chemical compounds has been in the study of chlorophyll biosynthesis in plants, algae and cyanobacteria. Chlorophyllide a is also an intermediate in the biosynthesis of bacteriochlorophylls.

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