8/13/2021 Chlorophyll a - Wikipedia

Chlorophyll a
Chlorophyll a is a specific form of chlorophyll used in oxygenic
photosynthesis. It absorbs most energy from wavelengths of Chlorophyll a
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, diffusively reflected by structures like
cell walls, becomes enriched in the reflected light.[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
Molecular structure
Chlorin ring
Side chains
Hydrocarbon tail
Biosynthesis
Reactions of photosynthesis
Absorbance of light
Light spectrum
Light gathering
Primary electron donation
See also Names
References IUPAC name
External links Chlorophyll a
Systematic IUPAC name
Magnesium [methyl
Distribution of chlorophyll a (3S,4S,21R)-14-ethyl-4,8,13,18-
tetramethyl-20-oxo-3-(3-oxo-3-
{[(2E,7R,11R)-3,7,11,15-
Chlorophyll a is essential for most photosynthetic organisms to tetramethyl-2-hexadecen-1-
release chemical energy but is not the only pigment that can be yl]oxy}propyl)-9-vinyl-21-
used for photosynthesis. All oxygenic photosynthetic organisms phorbinecarboxylatato(2−)-κ2N,N′]
use chlorophyll a, but differ in accessory pigments like Other names
chlorophyll b.[5] Chlorophyll a can also be found in very small α-Chlorophyll
quantities in the green sulfur bacteria, an anaerobic
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photoautotroph.[7] These organisms use bacteriochlorophyll and Identifiers

some chlorophyll a but do not produce oxygen.[7] Anoxygenic CAS Number 479-61-8 
photosynthesis is the term applied to this process, unlike
oxygenic photosynthesis where oxygen is produced during the 3D model Interactive image (htt
light reactions of photosynthesis. (JSmol)
ps://chemapps.stolaf.
edu/jmol/jmol.php?m
Molecular structure odel=CCC1%3DC%2
8C2%3DNC1%3DCC
The molecular structure of chlorophyll a consists of a chlorin 3%3DC%28C4%3D
ring, whose four nitrogen atoms surround a central magnesium C%28%5BN-%5D3%
atom, and has several other attached side chains and a 29C%28%3DC5%5B
hydrocarbon tail. C%40H%5D%28%5B
C%40%40H%5D%28
C%28%3DN5%29
C%3DC6C%28%3D
C%28C%28%3DC
2%29%5BN-%5D6%
29C%3DC%29C%29
C%29CCC%28%3D
O%29OC%2FC%3D
C%28%5CC%29%2F
CCCC%28C%29CC
CC%28C%29CCC
C%28C%29C%29%5
BC%40H%5D%28C
4%3DO%29C%28%3
DO%29OC%29C%29
C.%5BMg%2B2%5D)
Interactive image (htt
ps://chemapps.stolaf.
Structure of chlorophyll a molecule showing the long hydrocarbon tail edu/jmol/jmol.php?m
odel=COC%28%3D
O%29C9C%28%3D
Chlorin ring
O%29c6c%28C%29c
Chlorophyll a contains a magnesium ion 3n7c6c9c2C%28CC
encased in a large ring structure known as a C%28%3DO%29CO
chlorin. The chlorin ring is a heterocyclic CC%3DC%28C%29
compound derived from pyrrole. Four CCCC%28C%29CC
nitrogen atoms from the chlorin surround CC%28C%29CCC
Chlorin, the and bind the magnesium atom. The C%28C%29C%29
central ring magnesium center uniquely defines the C%28C%29c1cc5n8
structure of the structure as a chlorophyll molecule.[8] The c%28cc4n%28%5BM
chlorophyll a porphyrin ring of bacteriochlorophyll is
g%5D78n12%29c%2
saturated, and lacking alternation of double
8c%3D3%29c%28C
and single bonds causing variation in
C%29c4c%29c%28
absorption of light.[9]
C%3DC%29c5C)

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Side chains ChemSpider 16736115 (http://ww

w.chemspider.com/C
Side chains are attached to the hemical-Structure.16
chlorin ring of the various 736115.html) 
chlorophyll molecules. Different side
ECHA 100.006.852 (https://e
chains characterize each type of
chlorophyll molecule, and alters the InfoCard cha.europa.eu/substa
absorption spectrum of light.[10]
[11] nce-information/-/sub
For instance, the only difference stanceinfo/100.006.8
between chlorophyll a and 52)
chlorophyll b is that chlorophyll b EC Number 207-536-6
The green boxed CH3 is
has an aldehyde instead of a methyl
the methyl group at the C-
group at the C-7 position.[11] PubChem 6433192 (https://pubc
7 position chlorophyll a CID
hem.ncbi.nlm.nih.gov/
compound/6433192)
Hydrocarbon tail
RTECS FW6420000
Chlorophyll a has a long hydrophobic tail, which anchors the number
molecule to other hydrophobic proteins in the thylakoid UNII YF5Q9EJC8Y (http
membrane of the chloroplast.[5] Once detached from the
s://fdasis.nlm.nih.gov/
porphyrin ring, this long hydrocarbon tail becomes the
srs/srsdirect.jsp?regn
precursor of two biomarkers, pristane and phytane, which are
important in the study of geochemistry and the determination of o=YF5Q9EJC8Y) 
petroleum sources. CompTox DTXSID90889346 (ht
Dashboard
tps://comptox.epa.go
(EPA)
Biosynthesis v/dashboard/DTXSID
90889346)
The Chlorophyll a biosynthetic pathway utilizes a variety of InChI
enzymes.[12] In most plants, chlorophyll is derived from
InChI=1S/C55H73N4O5.Mg/c1-13-39-
glutamate and is synthesised along a branched pathway that is
35(8)42-28-44-37(10)41(24-25-48
shared with heme and siroheme.[13][14][15]
The initial steps (60)64-27-26-34(7)23-17-22-33(6)2
incorporate glutamic acid into 5-aminolevulinic acid (ALA); two 1-16-20-32(5)19-15-18-31(3)4)52(5
molecules of ALA are then reduced to porphobilinogen (PBG), 8-44)50-51(55(62)63-12)54(61)49-
and four molecules of PBG are coupled, forming protoporphyrin 38(11)45(59-53(49)50)30-47-40(14
-2)36(9)43(57-47)29-46(39)56-42;/
IX.[8] h13,26,28-33,37,41,51H,1,14-25,2
7H2,2-12H3,(H-,56,57,58,59,61);/q
Chlorophyll synthase[16] is the enzyme that completes the -1;+2/p-1/b34-26+;/t32-,33-,37+,41
biosynthesis of chlorophyll a[17][18] by catalysing the reaction EC +,51-;/m1./s1 
2.5.1.62 (https://enzyme.expasy.org/EC/2.5.1.62) Key: ATNHDLDRLWWWCB-AENOIHS
ZSA-M 
chlorophyllide a + phytyl diphosphate chlorophyll a + InChI=1S/C55H73N4O5.Mg/c1-13-39-
diphosphate 35(8)42-28-44-37(10)41(24-25-48
(60)64-27-26-34(7)23-17-22-33(6)2
This forms an ester of the carboxylic acid group in 1-16-20-32(5)19-15-18-31(3)4)52(5
chlorophyllide a with the 20-carbon diterpene alcohol phytol. 8-44)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;/
Reactions of photosynthesis h13,26,28-33,37,41,51H,1,14-25,2
7H2,2-12H3,(H-,56,57,58,59,61);/q
-1;+2/p-1/b34-26+;/t32?,33?,37-,41
-,51+;/m0./s1
Absorbance of light
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Light spectrum Key: ATNHDLDRLWWWCB-WJQLOW

BJSA-M
Chlorophyll a absorbs light SMILES
within the violet, blue and
CCC1=C(C2=NC1=CC3=C(C4=C([N-]
red wavelengths while 3)C(=C5[C@H]([C@@H](C(=N5)C
mainly reflecting green. This =C6C(=C(C(=C2)[N-]6)C=C)C)C)C
reflectance gives chlorophyll CC(=O)OC/C=C(\C)/CCCC(C)CCC
its green appearance. C(C)CCCC(C)C)[C@H](C4=O)C(=
Accessory photosynthetic O)OC)C)C.[Mg+2]
pigments broaden the COC(=O)C9C(=O)c6c(C)c3n7c6c9c2
spectrum of light absorbed, C(CCC(=O)COCC=C(C)CCCC(C)
increasing the range of CCCC(C)CCCC(C)C)C(C)c1cc5n8
c(cc4n([Mg]78n12)c(c=3)c(CC)c4c)
wavelengths that can be
c(C=C)c5C
Absorption spectrum of chlorophyll a
used in photosynthesis.[5]
and chlorophyll b. The use of both
The addition of chlorophyll Properties
together enhances the size of the b next to chlorophyll a Chemical C55H72MgN4O5
absorption of light for producing extends the absorption formula
energy. spectrum. In low light
Molar mass 893.509 g·mol−1
conditions, plants produce a
greater ratio of chlorophyll b Appearance Green
to chlorophyll a molecules, increasing photosynthetic yield.[10] Odor Odorless
Density 1.079 g/cm3[1]
Light gathering Melting point ~ 152.3 °C (306.1 °F;
425.4 K)[2]

Absorption of light by photosynthetic pigments converts

decomposes[1]
photons into chemical energy. Light energy radiating onto the
chloroplast strikes the pigments in the thylakoid membrane and Solubility in Insoluble
excites their electrons. Since the chlorophyll a molecules only water
capture certain wavelengths, organisms may use accessory Solubility Very soluble in
pigments to capture a wider range of light energy shown as the ethanol, ether

yellow circles.[6] It then transfers captured light from one Soluble in ligroin,[2]
pigment to the next as resonance energy, passing energy one acetone, benzene,
pigment to the other until reaching the special chlorophyll a
chloroform[1]
molecules in the reaction center.[10] These special chlorophyll a
molecules are located in both photosystem II and photosystem I. Absorbance See text
They are known as P680 for Photosystem II and P700 for Except where otherwise noted, data
Photosystem I.[19] P680 and P700 are the primary electron are given for materials in their
donors to the electron transport chain. These two systems are standard state (at 25 °C [77 °F],
100 kPa).
different in their redox potentials for one-electron oxidation.
The Em for P700 is approximately 500mV, while the Em for  verify (what is   ?)
P680 is approximately 1,100-1,200 mV.[19] Infobox references

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.[19]

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See also
Photosystem II light harvesting protein
Chlorophyll b, another related chemical
Chlorophyll c, an accessory pigment of chlorophyll
The antenna complex with
energy transfer within the
References thylakoid membrane of a
chloroplast. Chlorophyll a
1. Anatolievich KR. "Chlorophyll a" (https://web.archive.org/web/2014112 in the reaction center is
9080648/http://chemister.ru/Database/properties-en.php?dbid=1&id=1 the only pigment to pass
870). chemister.ru. Archived from the original (http://chemister.ru/Data boosted electrons to an
base/properties-en.php?dbid=1&id=1870) on 2014-11-29. Retrieved acceptor (modified from
2014-08-23. 2).
2. Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics
(90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
3. "Photosynthesis" (https://web.archive.org/web/20091128090227/http://
www.emc.maricopa.edu/faculty/farabee/BIOBK/BioBookPS.html).
Archived from the original (http://www.emc.maricopa.edu/faculty/farab
ee/BIOBK/BioBookPS.html) on 2009-11-28.
4. Virtanen O, Constantinidou E, Tyystjärvi E (December 2020).
"Chlorophyll does not reflect green light - how to correct a
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19266.2020.1858930).
5. Raven PH, Evert RF, Eichhorn SE (2005). "Photosynthesis, Light, and
Life". Biology of Plants (7th ed.). W. H. Freeman. pp. 119–127.
ISBN 0-7167-9811-5.
6. Papageorgiou G, Govindjee (2004). Chlorophyll a Fluorescence, A
Signature of Photosynthesis. Advances in Photosynthesis and
Respiration. 19. Springer. p. 14, 48, 86.
7. Eisen JA, Nelson KE, Paulsen IT, Heidelberg JF, Wu M, Dodson RJ,
et al. (July 2002). "The complete genome sequence of Chlorobium
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ps://www.ncbi.nlm.nih.gov/pmc/articles/PMC123171). Proceedings of
the National Academy of Sciences of the United States of America. 99
(14): 9509–14. Bibcode:2002PNAS...99.9509E (https://ui.adsabs.harv
ard.edu/abs/2002PNAS...99.9509E). doi:10.1073/pnas.132181499 (htt
ps://doi.org/10.1073%2Fpnas.132181499). PMC 123171 (https://www.
ncbi.nlm.nih.gov/pmc/articles/PMC123171). PMID 12093901 (https://p
ubmed.ncbi.nlm.nih.gov/12093901).
8. Zeiger E, Taiz L (2006). "Ch. 7: Topic 7.11: Chlorophyll Biosynthesis"
(http://4e.plantphys.net/article.php?ch=0&id=76). Plant physiology
(4th ed.). Sunderland, MA: Sinauer Associates. ISBN 0-87893-856-7.
9. Campbell MK, Farrell SO (20 November 2007). Biochemistry (https://b
ooks.google.com/books?id=NYa45_BxgukC&pg=PA647) (6th ed.).
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Ecology I – Responses to the Physical Environment. 12A. Springer-
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11. Niedzwiedzki DM, Blankenship RE (December 2010). "Singlet and

triplet excited state properties of natural chlorophylls and
bacteriochlorophylls". Photosynthesis Research. 106 (3): 227–38.
doi:10.1007/s11120-010-9598-9 (https://doi.org/10.1007%2Fs11120-0
10-9598-9). PMID 21086044 (https://pubmed.ncbi.nlm.nih.gov/210860
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12. Suzuki JY, Bollivar DW, Bauer CE (1997). "Genetic analysis of
chlorophyll biosynthesis". Annual Review of Genetics. 31 (1): 61–89.
doi:10.1146/annurev.genet.31.1.61 (https://doi.org/10.1146%2Fannure
v.genet.31.1.61). PMID 9442890 (https://pubmed.ncbi.nlm.nih.gov/944
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13. Battersby, A. R. (2000). "Tetrapyrroles: the Pigments of Life. A
Millennium review". Nat. Prod. Rep. 17 (6): 507–526.
doi:10.1039/B002635M (https://doi.org/10.1039%2FB002635M).
PMID 11152419 (https://pubmed.ncbi.nlm.nih.gov/11152419).
14. Akhtar, M. (2007). "The Modification of Acetate and Propionate Side
Chains During the Biosynthesis of Haem and Chlorophylls:
Mechanistic and Stereochemical Studies". Ciba Foundation
Symposium 180 - the Biosynthesis of the Tetrapyrrole Pigments.
Novartis Foundation Symposia. 180. pp. 131–155.
doi:10.1002/9780470514535.ch8 (https://doi.org/10.1002%2F9780470
514535.ch8). ISBN 9780470514535. PMID 7842850 (https://pubmed.n
cbi.nlm.nih.gov/7842850).
15. Willows, Robert D. (2003). "Biosynthesis of chlorophylls from
protoporphyrin IX". Natural Product Reports. 20 (6): 327–341.
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PMID 12828371 (https://pubmed.ncbi.nlm.nih.gov/12828371).
16. Schmid, H. C.; Rassadina, V.; Oster, U.; Schoch, S.; Rüdiger, W.
(2002). "Pre-Loading of Chlorophyll Synthase with Tetraprenyl
Diphosphate is an Obligatory Step in Chlorophyll Biosynthesis" (http
s://epub.ub.uni-muenchen.de/17847/1/bc.2002.198.pdf) (PDF).
Biological Chemistry. 383 (11): 1769–78. doi:10.1515/BC.2002.198 (ht
tps://doi.org/10.1515%2FBC.2002.198). PMID 12530542 (https://pubm
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17. Eckhardt, Ulrich; Grimm, Bernhard; Hortensteiner, Stefan (2004).
"Recent advances in chlorophyll biosynthesis and breakdown in higher
plants". Plant Molecular Biology. 56 (1): 1–14. doi:10.1007/s11103-
004-2331-3 (https://doi.org/10.1007%2Fs11103-004-2331-3).
PMID 15604725 (https://pubmed.ncbi.nlm.nih.gov/15604725).
S2CID 21174896
(https://api.semanticscholar.org/CorpusID:21174896).
18. Bollivar, David W. (2007). "Recent advances in chlorophyll
biosynthesis". Photosynthesis Research. 90 (2): 173–194.
doi:10.1007/s11120-006-9076-6 (https://doi.org/10.1007%2Fs11120-0
06-9076-6). PMID 17370354 (https://pubmed.ncbi.nlm.nih.gov/173703
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19. Ishikita H, Saenger W, Biesiadka J, Loll B, Knapp EW (June 2006).

"How photosynthetic reaction centers control oxidation power in
chlorophyll pairs P680, P700, and P870" (https://www.ncbi.nlm.nih.go
v/pmc/articles/PMC1502543). Proceedings of the National Academy of
Sciences of the United States of America. 103 (26): 9855–60.
Bibcode:2006PNAS..103.9855I (https://ui.adsabs.harvard.edu/abs/200
6PNAS..103.9855I). doi:10.1073/pnas.0601446103 (https://doi.org/10.
1073%2Fpnas.0601446103). PMC 1502543 (https://www.ncbi.nlm.nih.
gov/pmc/articles/PMC1502543). PMID 16788069 (https://pubmed.ncb
i.nlm.nih.gov/16788069).

External links
Zeiger & Taiz 2006, Topic 7.11: Chlorophyll Biosynthesis

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