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22-AUGUST-2008 06:13:22 - Chlorophyll Chlorophyll gives leaves their green color Chlorophyll gives leaves their green color Chlorophyll is found in high concentrations in chloroplasts of plant cells. Chlorophyll is found in high concentrations in chloroplasts of plant cells. SeaWIFS-derived average sea surface chlorophyll for the period 1998 to 2006. SeaWIFS-derived average sea surface chlorophyll for the period 1998 to 2006. Chlorophyll is a green pigment found in most plants, algae, and cyanobacteria. Its name is derived from Greek: chloros = green and phyllon = leaf. Chlorophyll absorbs light most strongly in the blue and red but poorly in the green portions of the electromagnetic spectrum, hence the green color of chlorophyll-containing tissues like plant leaves.1 Contents 1 Chlorophyll and photosynthesis 2 Chemical structure 3 Spectrophotometry 4 Biosynthesis 5 Culinary Use 6 See also 7 References 8 External links Chlorophyll and photosynthesis Chlorophyll is vital for photosynthesis, which allows plants to obtain energy from light. Chlorophyll molecules are specifically arranged in and around pigment protein complexes called photosystems which are embedded in the thylakoid membranes of chloroplasts. In these complexes, chlorophyll serves two primary functions. The function of the vast majority of chlorophyll up to several hundred per photosystem is to absorb light and transfer that light energy by resonance energy transfer to a specific chlorophyll pair in the reaction center of the photosystems. Because of chlorophyll's selectivity regarding the wavelength of light it absorbs, areas of a leaf containing the molecule will appear green. There are currently two accepted photosystem units, Photosystem II and Photosystem I, which have their own distinct reaction center chlorophylls, named P680 and P700, respectively.2 These pigments are named after the wavelength in nanometers of their red-peak absorption maximum. The identity, function and spectral properties of the types of chlorophyll in each photosystem are distinct and determined by each other and the protein structure surrounding them. Once extracted from the protein into a solvent such as acetone or methanol, these chlorophyll pigments can be separated in a simple paper chromatography experiment, and, based on the number of polar groups between chlorophyll a and chlorophyll b, will chemically separate out on the paper. The function of the reaction center chlorophyll is to use the energy absorbed by and transferred to it from the other chlorophyll pigments in the photosystems to undergo a charge separation, a specific redox reaction in which the chlorophyll donates an electron into a series of molecular intermediates called an electron transport chain. The charged reaction center chlorophyll P680+ is then reduced back to its ground state by accepting an electron. In Photosystem II, the electron which reduces P680+ ultimately comes from the oxidation of water into O2 and H+ through several intermediates. This reaction is how photosynthetic organisms like plants produce O2 gas, and is the source for practically all the O2 in Earth's atmosphere. Photosystem I typically works in series with Photosystem II, thus the P700+ of Photosystem I is usually reduced, via many intermediates in the thylakoid membrane, by electrons ultimately from Photosystem II. Electron transfer reactions in the thylakoid membranes are complex, however, and the source of electrons used to reduce P700+ can vary. The electron flow produced by the reaction center chlorophyll pigments is used to shuttle H+ ions across the thylakoid membrane, setting up a chemiosmotic potential mainly used to produce ATP chemical energy, and those electrons ultimately reduce NADP+ to NADPH a universal reductant used to reduce CO2 into sugars as well as for other biosynthetic reductions. Reaction center chlorophyll-protein complexes are capable of directly absorbing light and performing charge separation events without other chlorophyll pigments, but the absorption cross section the likelihood of absorbing a photon under a given light intensity is small. Thus, the remaining chlorophylls in the photosystem and antenna pigment protein complexes associated with the photosystems all cooperatively absorb and funnel light energy to the reaction center. Besides chlorophyll a, there are other pigments, called accessory pigments, which occur in these pigment-protein antenna complexes. Chemical structure Space-filling model of the chlorophyll a molecule Space-filling model of the chlorophyll a molecule Chlorophyll is a chlorin pigment, which is structurally similar to and produced through the same metabolic pathway as other porphyrin pigments such as heme. At the center of the chlorin ring is a magnesium ion. The chlorin ring can have several different side chains, usually including a long phytol chain. There are a few different forms that occur naturally, but the most widely distributed form in terrestrial plants is chlorophyll a. The general structure of chlorophyll a was elucidated by Hans Fischer in 1940, and by 1960, when most of the stereochemistry of chlorophyll a was known, Robert Burns Woodward published a total synthesis of the molecule as then known.3 In 1967, the last remaining stereochemical elucidation was completed by Ian Fleming,4 and in 1990 Woodward and co-authors published an updated synthesis.5 The different structures of chlorophyll are summarized below: Chlorophyll a Chlorophyll b Chlorophyll c1 Chlorophyll c2 Chlorophyll d Molecular formula C55H72O5N4Mg C55H70O6N4Mg C35H30O5N4Mg C35H28O5N4Mg C54H70O6N4Mg C3 group -CH=CH2 -CH=CH2 -CH=CH2 -CH=CH2 -CHO C7 group -CH3 -CHO -CH3 -CH3 -CH3 C8 group -CH2CH3 -CH2CH3 -CH2CH3 -CH=CH2 -CH2CH3 C17 group -CH2CH2COO-Phytyl -CH2CH2COO-Phytyl -CH=CHCOOH -CH=CHCOOH -CH2CH2COO-Phytyl C17-C18 bond Single Single Double Double Single Occurrence Universal Mostly plants Various algae Various algae cyanobacteria Structure of chlorophyll a Structure of chlorophyll a Structure of chlorophyll b Structure of chlorophyll b Structure of chlorophyll d Structure of chlorophyll d Structure of chlorophyll c1 Structure of chlorophyll c1 Structure of chlorophyll c2 Structure of chlorophyll c2 When leaves degreen in the process of plant senescence chlorophyll is converted to a group of colorless tetrapyrroles known as nonfluorescent chlorophyll catabolites NCC's with the general structure: Nonfluorescent chlorophyll catabolites These compounds have also been identified in several ripening fruits.6 Spectrophotometry Absorbance spectra of free chlorophyll a green and b red in a solvent. The spectra of chlorophyll molecules are slightly modified in vivo depending on specific pigment-protein interactions. Absorbance spectra of free chlorophyll a green and b red in a solvent. The spectra of chlorophyll molecules are slightly modified in vivo depending on specific pigment-protein interactions. Measurement of the absorption of light is complicated by the solvent used to extract it from plant material, which affects the values obtained, In diethyl ether, chlorophyll a has approximate absorbance maxima of 430 nm and 662 nm, while chlorophyll b has approximate maxima of 453 nm and 642 nm.7 The absorption peaks of Chlorophyll a are at 665 nm and 465 nm. Chlorophyll a fluoresces at 673 nm. The peak molar absorption coefficient of chlorophyll a exceeds 105 M-1 cm-1, which is among the highest for organic compounds. Biosynthesis Further information: Chlorosis In plants, chlorophyll may be synthesized from succinyl-CoA and glycine, although the immediate precursor to chlorophyll a and b is protochlorophyll. Chlorosis is a condition in which leaves produce insufficient chlorophyll, turning them yellow. Chlorosis can be caused by a nutrient deficiency including iron - called iron chlorosis, or in a shortage of magnesium or nitrogen. Soil pH sometimes play a role in nutrient-caused chlorosis, many plants are adapted to grow in soils with specific pHs and their ability to absorb nutrients from the soil can be dependent on the soil pH.8 Chlorosis can also be caused by pathogens including viruses, bacteria and fungal infections or sap sucking insects. Culinary Use Chefs use chlorophyll to color a variety of different dishes green, such as pasta. Chlorophyll is not soluble in water and is first mixed with a small quantity of oil to obtain the desired result. See also Bacteriochlorophyll, related compounds in phototrophic bacteria Chlorophyllin, a semi-synthetic derivative of chlorophyll Grow light, a lamp that promotes photosynthesis References ^ Speer, Brian R. 1997. Photosynthetic Pigments in UCMP Glossary online. University of California, Berkeley Museum of Paleontology. Verified availability March 12, 2007. ^ Green, 1984 ^ R. B. Woodward, W. A. Ayer, J. M. Beaton, F. Bickelhaupt, R. Bonnett, P. Buchschacher, G. L. Closs, H. Dutler, J. Hannah, F. P. Hauck, S. Itô, A. Langemann, E. Le Goff, W. Leimgruber, W. Lwowski, J. Sauer, Z. Valenta, and H. Volz 1960. The total synthesis of chlorophyll. Journal of the American Chemical Society 82: 3800-3802. doi:10.1021/ja01499a093. ^ Ian Fleming October 1967. Absolute Configuration and the Structure of Chlorophyll. Nature 216: 151-152. doi:10.1038/216151a0. ^ Robert Burns Woodward, William A. Ayer, John M. Beaton, Friedrich Bickelhaupt, Raymond Bonnett, Paul Buchschacher, Gerhard L. Closs, Hans Dutler, John Hannah, Fred P. Hauck, et al. 1990. The total synthesis of chlorophyll a. Tetrahedron 46 22: 7599-7659. doi:10.1016/0040-40209080003-Z. ^ Colorless Tetrapyrrolic Chlorophyll Catabolites Found in Ripening Fruit Are Effective Antioxidants Thomas Muller, Markus Ulrich, Karl-Hans Ongania, and Bernhard Krautler Angew. Chem. Int. Ed. 2007, 46, 8699 -8702 doi:10.1002/anie.200703587 ^ Gross, 1991 ^ Iron Chlorosis in Turfgrass External links Oregon University of Health Sciences PDF review-Chlorophyll d: the puzzle resolved Light Absorption by Chlorophyll - NIH books v d e Botany Subdisciplines of botany Ethnobotany · Paleobotany · Plant anatomy · Plant ecology · Plant evo-devo · Plant morphology · Plant physiology Plants Evolutionary history of plants · Algae · Bryophyte · Pteridophyte · Gymnosperm · Angiosperm Plant parts Flower · Fruit · Leaf · Meristem · Root · Stem · Stoma · Vascular tissue · Wood Plant cells Cell wall · Chlorophyll · Chloroplast · Photosynthesis · Plant hormone · Plastid · Transpiration Plant life cycles Gametophyte · Plant sexuality · Pollen · Pollination · Seed · Spore · Sporophyte Plant taxonomy Botanical name · Botanical nomenclature · Herbarium · IAPT · ICBN · Species Plantarum Category · Portal v d e Types of Plant Pigments Flavonoids Anthocyanins Anthocyanidins Anthoxanthins Proanthocyanidins Tannins Betalains Betacyanins Betaxanthins Carotenoids Xanthophylls Carotenes Retinoids Other Chlorophyll Allophycocyanin Phycocyanin Phycoerythrin Phycoerythrocyanin Quinones Xanthones Retrieved from http://en..org/wiki/Chlorophyll Categories: Tetrapyrroles | Photosynthetic pigments Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية Bosanski БългарÑ?ки Català Česky Cymraeg Dansk Deutsch Eesti Ελληνικά Español Esperanto Ù?ارسی Français Galego Hrvatski Bahasa Indonesia Italiano עברית ქáƒ?რთული Lietuvių Magyar МакедонÑ?ки Bahasa Melayu Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Occitan Polski Português Română Runa Simi РуÑ?Ñ?кий Simple English SlovenÄ?ina SlovenÅ¡Ä?ina СрпÑ?ки / Srpski Basa Sunda Suomi Svenska தமிழà¯? ไทย Tiếng Việt Türkçe УкраїнÑ?ька Walon This page was last modified on 31 July 2008, at 13:12
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