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Shikimate pathway

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The shikimate pathway (shikimic acid pathway) is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for the biosynthesis of folates and aromatic amino acids (tryptophan, phenylalanine, and tyrosine). This pathway is not found in mammals. The five enzymes involved in the shikimate pathway are 3-dehydroquinate dehydratase, shikimate dehydrogenase, shikimate kinase, EPSP synthase, and chorismate synthase.

Aromatic amino acidAromatic amino acidAn aromatic amino acid is an amino acid that includes an aromatic ring. Among the 20 standard amino acids, histidine, phenylalanine, tryptophan, tyrosine, are classified as aromatic. Properties and functionOptical propertiesAromatic amino acids, excepting histidine, absorb ultraviolet light above and beyond 250 nm and will fluoresce under these conditions.Shikimic acidShikimic acidNames Preferred IUPAC name(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-ene-1-carboxylic acidIdentifiers CAS Number138-59-03D model (JSmol)Interactive imageChEBICHEBI:16119ChEMBLChEMBL290345ChemSpider8412ECHA InfoCard100.004.850EC Number205-334-2KEGGC00493PubChemCID8742UNII29MS2WI2NUCompTox Dashboard(EPA)DTXSID4032039InChIInChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1Key: JXOHGGNKMLTUBP-HSUXUTPPSA-NInChI=1/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1/f/h11HInChI=1/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1Key: JXOHGGNKMLTUBP-HSUXUTPPBZSMILESC1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)OProperties Chemical formulaC7H10O5Molar mass174.15 g/mol Melting point185 to 187 °C (365 to 369 °F; 458 to 460 K) Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Nverify ( ?)Metabolic pathwayMetabolic pathwayIn biochemistry, a metabolic pathway is a linked series of chemical reactions occurring within a cell. The reactants, products, and intermediates of an enzymatic reaction are known as metabolites, which are modified by a sequence of chemical reactions catalyzed by enzymes. In most cases of a metabolic pathway, the product of one enzyme acts as the substrate for the next. However, side products are considered waste and removed from the cell.TyrosineTyrosineNames IUPAC nameTyrosineSystematic IUPAC name2-Amino-3-(4-hydroxyphenyl)propanoic acidIdentifiers CAS Number60-18-4 (L)3D model (JSmol)Interactive imageZwitterion: Interactive imageChEBICHEBI:17895ChEMBLChEMBL925ChemSpider5833DrugBankDB00135ECHA InfoCard100.000.419IUPHAR/BPS4791KEGGC00082PubChemCID6057UNII42HK56048UCompTox Dashboard(EPA)DTXSID1023730InChIInChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1Key: OUYCCCASQSFEME-QMMMGPOBSA-NKey: OUYCCCASQSFEME-UHFFFAOYSA-NKey: OUYCCCASQSFEME-MRVPVSSYSA-NSMILESN[C@@H](Cc1ccc(O)cc1)C(O)=OZwitterion: [NH3+][C@@H](Cc1ccc(O)cc1)C([O-])=OProperties Chemical formulaC9H11NO3Molar mass181.191 g·mol Appearance white solid Solubility in water45.3 mg/100 mL Magnetic susceptibility (χ)−105.3·10 cm/mol Hazards NFPA 704 (fire diamond) 110Supplementary data page Tyrosine (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).L-Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins.ArchaeaArchaeaDomain of organismsExcluded(but cladistically included)EukaryotaSynonyms"Archaebacteria" Woese & Fox 1977"Archaeobacteria" Murray 1988"Mendocutes" Gibbons & Murray 1978"Mendosicutes" Murray 1984"Metabacteria" Hori and Osawa 1979"Neomura" Cavalier-Smith 2002"Archaebiota" Luketa 2012"Arkarya" Forterre 2015Archaea ( ) is a domain of organisms.BiosynthesisBiosynthesisProcess where substrates are converted into more complex products in living organisms Biosynthesis is chemical synthesis occurring in biological contexts. It most often refers to multi-step, enzyme-catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthesis) serve as enzyme substrates, with conversion by the living organism either into simpler or more complex products.FolateFolateFolate, also known as vitamin B9 and folacin, is one of the B vitamins. Folate is required for the body to make DNA and RNA and metabolize amino acids necessary for cell division and maturation of blood cells. As the human body cannot make folate, it is required in the diet, making it an essential nutrient. It occurs naturally in many foods. The recommended adult daily intake of folate in the U.S. is 400 micrograms from foods or dietary supplements.TryptophanTryptophanNames IUPAC nameTryptophanSystematic IUPAC name2-Amino-3-(1H-indol-3-yl)propanoic acidOther names 2-Amino-3-(1H-indol-3-yl)propionic acidIdentifiers CAS Number73-22-33D model (JSmol)Interactive imageZwitterion: Interactive imageChEBICHEBI:16828ChEMBLChEMBL54976ChemSpider6066DrugBankDB00150ECHA InfoCard100.000.723IUPHAR/BPS717KEGGD00020PubChemCID6305UNII8DUH1N11BXCompTox Dashboard(EPA)DTXSID5021419InChIInChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1Key: QIVBCDIJIAJPQS-VIFPVBQESA-NSMILESc1[nH]c2ccccc2c1C[C@H](N)C(=O)OZwitterion: c1[nH]c2ccccc2c1C[C@H]([NH3+])C(=O)[O-]Properties Chemical formulaC11H12N2O2Molar mass204.229 g·mol Solubility in waterSoluble: 0.23 g/L at 0 °C,11.4 g/L at 25 °C, 17.1 g/L at 50 °C, 27.95 g/L at 75 °C SolubilitySoluble in hot alcohol, alkali hydroxides; insoluble in chloroform.PhenylalaninePhenylalanineType of α-amino acidNames Pronunciation US: ; UK: IUPAC namePhenylalanineSystematic IUPAC name(S)-2-Amino-3-phenylpropanoic acidIdentifiers CAS NumberL: 63-91-2D/L: 150-30-1D: 673-06-33D model (JSmol)L: Interactive imageD: Interactive imageL Zwitterion: Interactive imageD Zwitterion: Interactive imageChEBIL: CHEBI:17295D/L: CHEBI:28044D: CHEBI:16998ChEMBLL: ChEMBL301523ChemSpiderL: 5910D/L: 969D: 64639DrugBankL: DB00120ECHA InfoCard100.000.517IUPHAR/BPSL: 3313KEGGL: D00021PubChemCIDL: 6140D/L: 994D: 71567UNIIL: 47E5O17Y3RD/L: 8P946UF12SD: 032K16VRCUCompTox Dashboard(EPA)L: DTXSID4040763InChIInChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1Key: COLNVLDHVKWLRT-QMMMGPOBSA-NL: Key: COLNVLDHVKWLRT-QMMMGPOBBCD/L: Key: COLNVLDHVKWLRT-UHFFFAOYSA-ND: Key: COLNVLDHVKWLRT-MRVPVSSYSA-NSMILESL: c1ccc(cc1)C[C@@H](C(=O)O)ND: c1ccc(cc1)C[C@H](C(=O)O)NL Zwitterion: [NH3+][C@@H](CC1=CC=CC=C1)C([O-])=OD Zwitterion: [NH3+][C@H](CC1=CC=CC=C1)C([O-])=OProperties Chemical formulaC9H11NO2Molar mass165.192 g·mol Solubility in water9.97 g/L at 0 °C 14.11 g/L at 25 °C 21.87 g/L at 50 °C 37.08 g/L at 75 °C 68.9 g/L at 100 °C Acidity (pKa) 1.83 (carboxyl), 9.13 (amino) Hazards NFPA 704 (fire diamond) 210Supplementary data page Phenylalanine (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Chemical compoundPhenylalanine ball and stick model spinningPhenylalanine (symbol Phe or F) is an α-amino acid with the formulaC9H11NO2.FungusFungusOrganism belonging to kingdom FungiA fungus (pl.: fungi or funguses) is any member of the group of eukaryotic organisms that includes yeasts, molds, and mushrooms. These organisms are classified in the biological kingdomFungi. A characteristic that places fungus in a different kingdom from plants, bacteria, and some protists is having chitin in their cell walls.ProtozoaProtozoaProtozoa (sing.: protozoan or protozoon; alternative plural: protozoans) are a polyphyletic group of single-celledeukaryotes, either free-living or parasitic, that feed on organic matter such as other microorganisms or organic debris. Historically, protozoans were regarded as "one-celled animals".PlantPlantPlants are the eukaryotic organisms that constitute the kingdom Plantae (/'plænteɪ/). They are predominantly photosynthetic or came from photosynthetic ancestors, meaning that they obtain their energy from sunlight by using the green pigment chlorophyll in their chloroplasts to produce sugars from carbon dioxide and water. Over the course of time, some plants have evolved to be parasitic, meaning they take energy from other organisms.BacteriaBacteriaDomain of microorganismsSynonyms"Bacteria" (Cohn 1872) Cavalier-Smith 1983"Bacteria" Haeckel 1894"Bacteria" Cavalier-Smith 2002"Bacteriaceae" Cohn 1872a"Bacteriobionta" Möhn 1984"Bacteriophyta" Schussnig 1925"Eubacteria" Woese and Fox 1977"Neobacteria" Möhn 1984"Schizomycetaceae" de Toni and Trevisan 1889"Schizomycetes" Nägeli 1857Bacteria are ubiquitous, mostly free-living organisms often consisting of one biological cell.

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