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{{Unreferenced|date=December 2009}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 370256222 |
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| verifiedrevid = 439934950 |
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|ImageFile=Uroporphyrinogen III skeletal.svg |
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| ImageFile=Uroporphyrinogen III skeletal.svg |
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|IUPACName= |
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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=1976-85-8 |
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| CASNo=1976-85-8 |
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| PubChem=1179 |
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| SMILES= |
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| PubChem=1179 |
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| MeSHName=Uroporphyrinogen+III |
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| MeSHName=Uroporphyrinogen+III |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>40</sub>H<sub>44</sub>N<sub>4</sub>O<sub>16</sub> |
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| Formula=C<sub>40</sub>H<sub>44</sub>N<sub>4</sub>O<sub>16</sub> |
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| MolarMass=836.795 g/mol |
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| MolarMass=836.795 g/mol |
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|Section3= {{Chembox Hazards |
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'''Uroporphyrinogen III''' is a ], the first ] intermediate in the ] of ], ], ], and ]. It is a colorless compound, like other ]s.<ref>{{cite journal |last1=Dalton |first1=J |title=Formation of the Macrocyclic Ring in Tetrapyrrole Biosynthesis |journal=Nature |volume=223 |issue=5211 |pages=1151–1153 |doi=10.1038/2231151a0 |pmid=5810686 |year=1969 |bibcode=1969Natur.223.1151D |s2cid=4177167 }}</ref> |
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'''Uroporphyrinogen III''' is an ] in the ] of ]. It is created by the enzyme ], and is converted into ] by the enzyme ]. |
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==Structure== |
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The ] of uroporphyrinogen III can be described as a ] core, where each ] ring has the ] atoms on its two outermost ]s replaced by an ] group ({{chem2|\sCH2\sCOOH}}, "A") and a ] group ({{chem2|\sCH2\sCH2\sCOOH}}, "P"). The groups are attached in an asymmetric way: going around the macrocycle, the order is AP-AP-AP-PA. |
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==Biosynthesis and metabolism== |
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In the general ] pathway, uroporphyrinogen III is derived from the linear tetrapyrrole ] (a substituted ]) by the action of the ] ].<ref name=Hemes>{{cite encyclopedia|chapter=Hemes in Biology|author=Paul R. Ortiz de Montellano|year=2008|encyclopedia=Wiley Encyclopedia of Chemical Biology|pages=1–10 |doi=10.1002/9780470048672.wecb221|publisher=John Wiley & Sons|isbn=978-0-470-04867-2}}</ref><ref name=sassa/> |
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<!--:] → ] + {{chem2|H2O}}--> |
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] |
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The conversion entails a reversal of the last ] unit (thus swapping the acetic and propionic acid groups) and a ] that closes the macrocycle by eliminating the final ] {{chem2|\sOH}} with a hydrogen atom of the first ring. |
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In the biosynthesis of hemes and chlorophylls, uroporphyrinogen III is converted into ] by the enzyme ]. In the biosynthesis of sirohemes, uroporphyrinogen III is converted by two methyl transferases to ], which is subsequently oxidized ], a precursor to the ] prosthetic group. |
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==Medical significance== |
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If uroporphyrinogen-III synthase is not present or inactive, the hydroxymethylbilane will spontaneously cyclise into the ] ], which differs from the III isomer in that the acetic acid ("A") and propionic acid ("P") groups are arranged in a rotationally symmetric order, AP-AP-AP-AP. In this case, the next step produced ], which accumulates — leading to the ] condition ]<ref name=sassa>S. Sassa and A. Kappas (2000): "Molecular aspects of the inherited porphyrias". ''Journal of Internal Medicine'', volume 247, issue 2, pages 169-178. {{doi|10.1046/j.1365-2796.2000.00618.x}}</ref> |
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==See also== |
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==See also== |
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*] |
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==References== |
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{{-}} |
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<references /> |
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] and some in the ] (yellow)]] |
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{{Tetrapyrroles}} |
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{{Tetrapyrroles}} |
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{{DEFAULTSORT:Uroporphyrinogen Iii}} |
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{{DEFAULTSORT:Uroporphyrinogen Iii}} |
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