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Latest revision as of 02:54, 5 December 2024 edit AlexZiky (talk | contribs)1 edit →Biosynthesis: The enzyme of CHLC synthase has been identified in Science, 2023Tag: Visual edit |
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{{DISPLAYTITLE:Chlorophyll ''c''}} |
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'''Chlorophyll ''c''''' refers to forms of ] found in certain marine algae, including the photosynthetic ] (e.g. ] and ]) and ].<ref name=foundin>{{cite web |last=Speer |first=B. R. |title=Photosynthetic Pigments |url=http://www.ucmp.berkeley.edu/glossary/gloss3/pigments.html |access-date=2 August 2014}}</ref><ref name="MolMech"/><ref name=SPDC>{{cite journal |vauthors=Dougherty RC, Strain HH, Svec WA, Uphaus RA, Katz JJ |title=The structure, properties, and distribution of chlorophyll c |journal=] |volume=92 |issue=9 |pages=2826–33 |date=May 1970 |pmid=5439971 |doi=10.1021/ja00712a037|bibcode=1970JAChS..92.2826D }}</ref> These pigments are characterized by their unusual chemical structure, with a ] as opposed to the ] (which has a reduced ring D) as the core; they also do not have an isoprenoid tail. Both these features stand out from the other chlorophylls commonly found in algae and plants.<ref name=MolMech>{{cite book|author1-link=Robert E. Blankenship |last=Blankenship |first=Robert E. |name-list-style=vanc |title=Molecular Mechanisms of Photosynthesis |date=February 2002 |publisher=]-Blackwell}}</ref> |
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| verifiedrevid = 416908601 |
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It has a blue-green color and is an ], particularly significant in its absorption of light in the 447–520 nm wavelength region.<ref name="SPDC" /> Like ] and ], it helps the organism gather light and passes a quanta of excitation energy through the light harvesting antennae to the ].<ref name=MolMech/> |
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Chlorophyll ''c'' can be further divided into chlorophyll ''c''<sub>1</sub>, chlorophyll ''c''<sub>2</sub>,<ref name="SPDC"/> and chlorophyll ''c''<sub>3</sub>,<ref name=c3>{{cite journal |vauthors=Fookes CJ, Jeffrey SW |title=The structure of chlorophyll ''c<sub>3</sub>'', a novel marine photosynthetic pigment |journal=J. Chem. Soc., Chem. Commun. |date=1989 |issue=23 |pages=1827–28 |doi=10.1039/C39890001827}}</ref> plus at least eight other more recently found subtypes.<ref name=CurrentStat>{{cite journal |last1=Zapata |first1=Manuel |last2=Garrido |first2=José L. |last3=Jeffrey |first3=Shirley W. |name-list-style=vanc |title=Chlorophyll c Pigments: Current Status |journal=Chlorophylls and Bacteriochlorophylls: Advances in Photosynthesis and Respiration |year=2006 |volume=25 |pages=39–53 |doi=10.1007/1-4020-4516-6_3 |series=Advances in Photosynthesis and Respiration |isbn=978-1-4020-4515-8}}</ref> |
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==Chlorophyll ''c''<sub>1</sub>== |
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'''Chlorophyll''' '''''c''<sub>1</sub>''' is a common form of chlorophyll ''c''. It differs from chlorophyll ''c''<sub>2</sub> in its C8 group, having an ethyl group instead of vinyl group (C-C single bond instead of C=C double bond). |
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Its ] are around 444, 577, 626 nm and 447, 579, 629 nm in ] and ] respectively.<ref name=Fawley>{{cite journal | vauthors = Fawley MW | title = A new form of chlorophyll C involved in light-harvesting | journal = Plant Physiology | volume = 91 | issue = 2 | pages = 727–32 | date = October 1989 | pmid = 16667093 | pmc = 1062062 | doi = 10.1104/pp.91.2.727 }}</ref> |
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{{-}} |
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==Chlorophyll ''c''<sub>2</sub>== |
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'''Chlorophyll''' '''''c''<sub>2</sub>''' is the most common form of chlorophyll ''c''.<ref name=c1c2compare>{{cite journal| vauthors = Jeffrey SW |title=The Occurrence of Chlorophyll ''c<sub>1</sub>'' and ''c<sub>2</sub>'' in Algae|journal=Journal of Phycology|date=September 1976|volume=12|issue=3|pages=349–354|doi=10.1111/j.1529-8817.1976.tb02855.x|bibcode=1976JPcgy..12..349J |s2cid=83927313 }}</ref> |
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Its absorption maxima are around 447, 580, 627 nm and 450, 581, 629 nm in diethyl ether and acetone respectively.<ref name=Fawley /> |
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{{-}} |
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==Chlorophyll ''c''<sub>3</sub>== |
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'''Chlorophyll''' '''''c''<sub>3</sub>''' is a form of chlorophyll ''c'' found in microalga '']'', identified in 1989.<ref name="c3"/> |
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Its absorption maxima are around 452, 585, 625 nm and 452, 585, 627 nm in diethyl ether and acetone respectively.<ref name=Fawley/> |
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{{-}} |
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== Biosynthesis == |
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Chlorophyll ''c'' synthesis branches off early from the typical ] synthesis pathway, after ]. It has been established that DV-PChlide and MV-PChlide are processed directly by a 17<sup>1</sup> oxidase ('''CHLC, chlorophyll ''c'' synthase''') into Chl ''c''<sub>2</sub> and Chl ''c''<sub>1</sub>, respectively.<ref name=":0">{{Cite journal |last=Jiang |first=Yanyou |last2=Cao |first2=Tianjun |last3=Yang |first3=Yuqing |last4=Zhang |first4=Huan |last5=Zhang |first5=Jingyu |last6=Li |first6=Xiaobo |date=2023-10-06 |title=A chlorophyll c synthase widely co-opted by phytoplankton |url=https://www.science.org/doi/10.1126/science.adg7921 |journal=Science |volume=382 |issue=6666 |pages=92–98 |doi=10.1126/science.adg7921}}</ref> |
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The 17<sup>1</sup> oxidtion was proposed to proceed by "hydroxylation of the 17-propionate reside at the 17<sup>1</sup>-position and successive dehydration to the 17-acrylate residue."<ref name=":0" /><ref>{{cite journal |last1=Xu |first1=M |last2=Kinoshita |first2=Y |last3=Matsubara |first3=S |last4=Tamiaki |first4=H |date=March 2016 |title=Synthesis of chlorophyll-c derivatives by modifying natural chlorophyll-a. |journal=Photosynthesis Research |volume=127 |issue=3 |pages=335–45 |bibcode=2016PhoRe.127..335X |doi=10.1007/s11120-015-0190-1 |pmid=26346903 |s2cid=254944200}}</ref> |
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An 8-vinyl reductase (elaborating on the promiscuous behavior of ferredoxin-type ]) could also convert Chl ''c''<sub>2</sub> into Chl ''c''<sub>1</sub>. The two steps could be swapped for the same effect.<ref>{{cite journal |last1=Ito |first1=Hisashi |last2=Tanaka |first2=Ayumi |title=Evolution of a New Chlorophyll Metabolic Pathway Driven by the Dynamic Changes in Enzyme Promiscuous Activity |journal=Plant and Cell Physiology |date=March 2014 |volume=55 |issue=3 |pages=593–603 |doi=10.1093/pcp/pct203 |pmid=24399236|hdl=2115/58225 |hdl-access=free }}</ref> |
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== Structure == |
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{| class="wikitable" style="text-align:center;width:100%;" |
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|- |
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! style="width:33%;" | Chlorophyll ''c''<sub>1</sub> |
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! style="width:33%;" | Chlorophyll ''c''<sub>2</sub> |
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! style="width:33%;" | Chlorophyll ''c''<sub>3</sub> |
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| valign="top" |{{Chembox |
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| Name= |
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| verifiedrevid = 429169129 |
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| ImageFile = Chlorophyll c1.svg |
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| ImageFile = Chlorophyll c1.svg |
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| ImageSize = |
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| ImageSize = |
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| ImageFile1 = Chlorophyll-c1-3D-balls.png |
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| ImageAlt1 = Chlorophyll c1 molecule |
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| IUPACName = acrylato(2-)]magnesium |
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| OtherNames = |
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|Section1={{Chembox Identifiers |
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| index1_label = c1 |
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| index2_label = c2 |
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| index3_label = c3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 11003-45-5 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 18901-56-9 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASNo2 = 27736-03-4 |
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| CASNo3_Ref = {{cascite|correct|CAS}} |
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| CASNo3 = 111308-93-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII= 1A9E276K41 |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1= 008W2KH70E |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2= 8GAP92KIWW |
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| UNII3_Ref = {{fdacite|correct|FDA}} |
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| UNII3= FMN10170B8 |
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| PubChem = 25245630 |
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| ChEBI = 38202 |
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| ChemSpiderID = 21865345 |
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| Beilstein = 5801077, 6996880 |
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| SMILES = CCC1=C(C)/C2=C/c3c(C=C)c(C)c4\C=C5/N=C(C(\C=C\C(O)=O)=C/5C)C5=c6c(C(=O)C5C(=O)OC)c(C)c(=CC1=N\2)n6n34 |
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| SMILES1 = COC(=O)C9C(=O)c6c(C)c3n7c6c9c2c(C=CC(=O)O)c(C)c1cc5n8c(cc4n(78n12)c(c=3)c(CC)c4c)c(C=C)c5C |
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| StdInChI = 1S/C35H32N4O5.Mg/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22;/h8,10-14,31H,1,9H2,2-7H3,(H3,36,37,38,39,40,41,42);/q;+2/p-2/b11-10+,22-12-,23-13-,24-12-,25-14-,26-13-,27-14-,32-30-; |
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| StdInChIKey = DGNIJJSSARBJSH-QRKQXEOSSA-L }} |
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|Section2={{Chembox Properties |
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| C=35 | H=30 | O=5 | N=4 | Mg=1 |
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| Appearance = |
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| Density = |
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| MeltingPt = |
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| BoilingPt = |
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| Solubility = }} |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = }} |
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}} |
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| valign="top" |{{Chembox |
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| Name= |
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| verifiedrevid = 428811250 |
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| ImageFile = Chlorophyll c2.svg |
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| ImageSize = 200px |
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| ImageFile1 = Chlorophyll-c2-3D-balls.png |
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| ImageAlt1 = Chlorophyll c2 molecule |
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| IUPACName = acrylato(2-)]magnesium |
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| OtherNames = |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 27736-03-4 |
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| PubChem = 16070018 |
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| ChemSpiderID = 21865346 |
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| ChEBI = 38203 |
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| UNII = 8GAP92KIWW |
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| Beilstein = 5801049 6996841 |
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| InChI=1S/C35H30N4O5.Mg/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22;/h8-14,31H,1-2H2,3-7H3,(H3,36,37,38,39,40,41,42);/q;+2/p-2/b11-10+,22-12?,23-13?,24-12?,25-14?,26-13?,27-14?,32-30?; |
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| InChIKey = QDRBYWCRXZZVLY-JUQUGTHISA-L |
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| SMILES = CC1=C(C2=CC3=NC(=CC4=C(C5=C(4)C(=C6C(=C(C(=N6)C=C12)C)C=CC(=O)O)C(C5=O)C(=O)OC)C)C(=C3C)C=C)C=C. |
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| SMILES1 = COC(=O)C9C(=O)c6c(C)c3n7c6c9c2c(C=CC(=O)O)c(C)c1cc5n8c(cc4n(78n12)c(c=3)c(C=C)c4c)c(C=C)c5C }} |
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|Section2={{Chembox Properties |
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| C=35 | H=28 | O=5 | N=4 | Mg=1 |
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| Appearance = |
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| Density = |
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| MeltingPt = |
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| BoilingPt = |
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| Solubility = }} |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = }} |
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}} |
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| valign="top" |{{Chembox |
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| Name= |
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| ImageFile = Chlorophyll c3.svg |
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| ImageSize = 200px |
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| ImageFile1 = |
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| ImageAlt1 = |
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| IUPACName = |
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| IUPACName = |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = |
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| PubChem = 25245630 |
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| CASNo = 111308-93-1 |
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| ChemSpiderID = 32699592 |
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| SMILES = }} |
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| PubChem = 71587417 |
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| Section2 = {{Chembox Properties |
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| C = 35 |
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| UNII = FMN10170B8 |
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| InChI=1S/C36H30N4O7.Mg/c1-8-18-15(3)21-12-22-16(4)20(10-11-27(41)42)32(39-22)30-31(36(45)47-7)34(43)28-17(5)23(40-33(28)30)13-25-19(9-2)29(35(44)46-6)26(38-25)14-24(18)37-21;/h8-14,31,38,43H,1-2H2,3-7H3,(H,41,42);/q;+2/p-2/b11-10+,21-12?,25-13?,26-14?,32-30?;/t31-;/m1./s1 |
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| H = 30 |
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| InChIKey = CWLZENTWIZFJMW-XUGDHDJXSA-L |
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| O = 5 |
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| SMILES = CC1=C(C2=NC1=CC3=NC(=C4C(C(=C5C4=NC(=C5C)C=C6C(=C(C(=C2)N6)C(=O)OC)C=C))C(=O)OC)C(=C3C)C=CC(=O))C=C. }} |
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| N = 4 |
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|Section2={{Chembox Properties |
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| Mg = 1 |
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| C=36 | H=28 | O=7 | N=4 | Mg=1 |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| BoilingPt = |
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| BoilingPt = |
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| Solubility = }} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = }} |
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| AutoignitionPt = }} |
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}} |
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}} |
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'''Chlorophyll c1''' is a form of ]. |
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it makes a golden or brownish color and is an accessary pigment. it helps the organism gather light but is not used in photosynthesis itself. |
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== References == |
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{{reflist}} |
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{{tetrapyrroles}} |
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{{tetrapyrroles}} |
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{{Plant pigments}} |
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{{Plant pigments}} |
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] |
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] |
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] |
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] |
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] |
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] |
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{{biochem-stub}} |
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] |
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