Chlorophyll b

Chlorophyll b
	Structure of β-Chlorophyll
Names
	IUPAC name Chlorophyll b
	Systematic IUPAC name Magnesium [methyl (3S,4S,21R)-14-ethyl-13-formyl-4,8,18-trimethyl-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 β-Chlorophyll
Identifiers
CAS Number	519-62-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	16739843 ;
ECHA InfoCard	100.007.522
EC Number	208-272-4;
E number	E140 (colours)
PubChem CID	6450186; 11593175 (from spinach);
UNII	5712ZB110R ;
CompTox Dashboard (EPA)	DTXSID70889349 ;
	InChI InChI=1S/C55H71N4O6.Mg/c1-12-38-35(8)42-27-43-36(9)40(23-24-48(61)65-26-25-34(7)22-16-21-33(6)20-15-19-32(5)18-14-17-31(3)4)52(58-43)50-51(55(63)64-11)54(62)49-37(10)44(59-53(49)50)28-46-39(13-2)41(30-60)47(57-46)29-45(38)56-42;/h12,25,27-33,36,40,51H,1,13-24,26H2,2-11H3,(H-,56,57,58,59,60,62);/q-1;+2/p-1/b34-25+;/t32-,33-,36+,40+,51-;/m1./s1 Key: NSMUHPMZFPKNMZ-VBYMZDBQSA-M ; InChI=1S/C55H72N4O6.Mg/c1-12-38-35(8)42-27-43-36(9)40(23-24-48(61)65-26-25-34(7)22-16-21-33(6)20-15-19-32(5)18-14-17-31(3)4)52(58-43)50-51(55(63)64-11)54(62)49-37(10)44(59-53(49)50)28-46-39(13-2)41(30-60)47(57-46)29-45(38)56-42;/h12,25,27-33,36,40,51H,1,13-24,26H2,2-11H3,(H2,56,57,58,59,60,62);/q;+2/p-2/b34-25+;/t32-,33-,36+,40+,51-;/m1./s1 Key: MSLKMRUEVOYOOZ-VBYMZDBQSA-L;
	SMILES CCC1=C(C2=NC1=CC3=C(C4=C([C@@H](C(=C4[N-]3)C5=NC(=CC6=NC(=C2)C(=C6C)C=C)[C@H]([C@@H]5CCC(=O)OC/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)C(=O)OC)[O-])C)C=O.[Mg+2];
Properties
Chemical formula	C55H70MgN4O6
Molar mass	907.492 g·mol−1
Appearance	Green
Odor	Odorless
Melting point	~ 125 °C (257 °F; 398 K)
Solubility in water	Insoluble
Solubility	Very soluble in ethanol, ether, pyridine; Soluble in methanol
Absorbance	See text
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[2]

In land plants, the light-harvesting antennae around photosystem II contain the majority of chlorophyll b. Hence, in shade-adapted chloroplasts, which have an increased ratio of photosystem II to photosystem I, there is a higher ratio of chlorophyll b to chlorophyll a.^[3] This is adaptive, as increasing chlorophyll b increases the range of wavelengths absorbed by the shade chloroplasts.


Structure of chlorophyll b molecule showing the long hydrocarbon tail

Biosynthesis

The Chlorophyll b biosynthetic pathway utilizes a variety of enzymes.^[4] In most plants, chlorophyll is derived from glutamate and is synthesised along a branched pathway that is shared with heme and siroheme.^[5]^[6]^[7] 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.

Chlorophyll synthase^[8] is the enzyme that completes the biosynthesis of chlorophyll b^[9]^[10] by catalysing the reaction EC 2.5.1.62

chlorophyllide b + phytyl diphosphate

\rightleftharpoons

chlorophyll b + diphosphate

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

References

^ ^a ^b ^c Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
^ "Photosynthesis pigments". Archived from the original on 2012-09-05. Retrieved 2011-01-13.
^ Kitajima, Kaoru; Hogan, Kevin P (2003). "Increases of chlorophyll a/b ratios during acclimation of tropical woody seedlings to nitrogen limitation and high light". Plant, Cell & Environment. 26 (6): 857–865. doi:10.1046/j.1365-3040.2003.01017.x. PMID 12803613.
^ 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. PMID 9442890.
^ Battersby, A. R. (2000). "Tetrapyrroles: the Pigments of Life. A Millennium review". Nat. Prod. Rep. 17 (6): 507–526. doi:10.1039/B002635M. PMID 11152419.
^ 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. Vol. 180. pp. 131–155. doi:10.1002/9780470514535.ch8. ISBN 9780470514535. PMID 7842850.
^ Willows, Robert D. (2003). "Biosynthesis of chlorophylls from protoporphyrin IX". Natural Product Reports. 20 (6): 327–341. doi:10.1039/B110549N. PMID 12828371.
^ 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" (PDF). Biological Chemistry. 383 (11): 1769–78. doi:10.1515/BC.2002.198. PMID 12530542. S2CID 3099209.
^ 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. PMID 15604725. S2CID 21174896.
^ Bollivar, David W. (2007). "Recent advances in chlorophyll biosynthesis". Photosynthesis Research. 90 (2): 173–194. doi:10.1007/s11120-006-9076-6. PMID 17370354. S2CID 23808539.

[crc-1] Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.

[2] "Photosynthesis pigments". Archived from the original on 2012-09-05. Retrieved 2011-01-13.

[3] Kitajima, Kaoru; Hogan, Kevin P (2003). "Increases of chlorophyll a/b ratios during acclimation of tropical woody seedlings to nitrogen limitation and high light". Plant, Cell & Environment. 26 (6): 857–865. doi:10.1046/j.1365-3040.2003.01017.x. PMID 12803613.

[biosynthesis_8-4] 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. PMID 9442890.

[5] Battersby, A. R. (2000). "Tetrapyrroles: the Pigments of Life. A Millennium review". Nat. Prod. Rep. 17 (6): 507–526. doi:10.1039/B002635M. PMID 11152419.

[akhtar94-6] 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. Vol. 180. pp. 131–155. doi:10.1002/9780470514535.ch8. ISBN 9780470514535. PMID 7842850.

[Review-7] Willows, Robert D. (2003). "Biosynthesis of chlorophylls from protoporphyrin IX". Natural Product Reports. 20 (6): 327–341. doi:10.1039/B110549N. PMID 12828371.

[8] 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" (PDF). Biological Chemistry. 383 (11): 1769–78. doi:10.1515/BC.2002.198. PMID 12530542. S2CID 3099209.

[9] 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. PMID 15604725. S2CID 21174896.

[10] Bollivar, David W. (2007). "Recent advances in chlorophyll biosynthesis". Photosynthesis Research. 90 (2): 173–194. doi:10.1007/s11120-006-9076-6. PMID 17370354. S2CID 23808539.

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Chlorophyll b

Biosynthesis

References

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