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Chlorophyll b

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]

Chlorophyll b
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
  • 519-62-0 N
3D model (JSmol)
  • Interactive image
ChemSpider
  • 16739843 Y
ECHA InfoCard 100.007.522
EC Number
  • 208-272-4
E number E140 (colours)
  • 6450186
  • 11593175 (from spinach)
UNII
  • 5712ZB110R N
  • DTXSID70889349
  • 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 Y
    Key: NSMUHPMZFPKNMZ-VBYMZDBQSA-M Y
  • 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
  • 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
C55H70MgN4O6
Molar mass 907.492 g·mol−1
Appearance Green
Odor Odorless
Melting point ~ 125 °C (257 °F; 398 K)[1]
Insoluble[1]
Solubility Very soluble in ethanol, ether, pyridine
Soluble in methanol[1]
Absorbance See text
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
The absorption spectrum of both the chlorophyll a and the chlorophyll b pigments. The use of both together enhances the size of the absorption of light for producing energy.

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 edit

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   chlorophyll b + diphosphate

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

References edit

  1. ^ 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.
  2. ^ . 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.
  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.
  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.
  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.

chlorophyll, form, chlorophyll, helps, photosynthesis, absorbing, light, energy, more, soluble, than, chlorophyll, polar, solvents, because, carbonyl, group, color, green, primarily, absorbs, blue, light, namesiupac, name, systematic, iupac, name, magnesium, m. 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 Chlorophyll b NamesIUPAC name Chlorophyll bSystematic 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 k2N N Other names b ChlorophyllIdentifiersCAS Number 519 62 0 N3D model JSmol Interactive imageChemSpider 16739843 YECHA InfoCard 100 007 522EC Number 208 272 4E number E140 colours PubChem CID 645018611593175 from spinach UNII 5712ZB110R NCompTox Dashboard EPA DTXSID70889349InChI 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 YKey NSMUHPMZFPKNMZ VBYMZDBQSA M YInChI 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 s1Key MSLKMRUEVOYOOZ VBYMZDBQSA LSMILES 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 PropertiesChemical formula C 55H 70Mg N 4O 6Molar mass 907 492 g mol 1Appearance GreenOdor OdorlessMelting point 125 C 257 F 398 K 1 Solubility in water Insoluble 1 Solubility Very soluble in ethanol ether pyridine Soluble in methanol 1 Absorbance See textExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references The absorption spectrum of both the chlorophyll a and the chlorophyll b pigments The use of both together enhances the size of the absorption of light for producing energy 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 tailBiosynthesis editMain article Chlorophyllide 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 displaystyle rightleftharpoons nbsp chlorophyll b diphosphateThis forms an ester of the carboxylic acid group in chlorophyllide b with the 20 carbon diterpene alcohol phytol References edit 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 amp 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 Rudiger 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 Retrieved from https en wikipedia org w index php title Chlorophyll b amp oldid 1169947788, wikipedia, wiki, book, books, library,

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