Carbamoyl phosphate: Difference between revisions
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| ImageFile = Carbamoylphosphat deprotoniert.svg |
| ImageFile = Carbamoylphosphat deprotoniert.svg |
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| ImageSize = 150px |
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| IUPACName = (Carbamoyloxy)phosphonic acid |
| IUPACName = (Carbamoyloxy)phosphonic acid |
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| OtherNames = |
| OtherNames = |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 590-55-6 |
| CASNo = 590-55-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = GC5KZW01Q3 |
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| PubChem = 278 |
| PubChem = 278 |
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| SMILES = C(=O)(N)OP(=O)(O)O |
| SMILES = C(=O)(N)OP(=O)(O)O |
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| MeSHName = Carbamoyl+phosphate |
| MeSHName = Carbamoyl+phosphate |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 17672 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 369105 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 272 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C00169 |
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| InChI = 1S/CH4NO5P/c2-1(3)7-8(4,5)6/h(H2,2,3)(H2,4,5,6) |
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| InChIKey = FFQKYPRQEYGKAF-UHFFFAOYSA-N |
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|Section2={{Chembox Properties |
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| Formula = CH<sub>2</sub>NO<sub>5</sub>P<sup> |
| Formula = CH<sub>2</sub>NO<sub>5</sub>P<sup>2−</sup> |
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| MolarMass = 141.020 g/mol |
| MolarMass = 141.020 g/mol |
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| Appearance = |
| Appearance = |
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| BoilingPt = |
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|Section3={{Chembox Hazards |
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| Solubility = |
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'''Carbamoyl phosphate''' is an [[anion]] of biochemical significance. |
'''Carbamoyl phosphate''' is an [[anion]] of biochemical significance. In land-dwelling animals, it is an [[Metabolic intermediate|intermediary metabolite]] in [[nitrogen]] disposal through the [[urea cycle]] and the synthesis of [[pyrimidine]]s. Its enzymatic counterpart, carbamoyl phosphate synthetase I (CPS I), interacts with a class of molecules called [[sirtuin]]s, NAD dependent protein deacetylases, and ATP to form carbamoyl phosphate. CP then enters the urea cycle in which it reacts with [[ornithine]] (a process catalyzed by the enzyme [[ornithine transcarbamylase]]) to form [[citrulline]]. |
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== Classification == |
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It is produced from [[bicarbonate]], [[ammonia]] (derived from [[glutamate]]), and [[phosphate]] (from [[Adenosine triphosphate|ATP]]). The synthesis is catalysed by the enzyme [[carbamoyl phosphate synthetase]], as follows: |
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Carbamoyl phosphate is a [[metabolic intermediate]] in a [[Metabolic pathway|pathway]] that involves [[nitrogen]] disposal through the [[urea cycle]] and the [[biosynthesis]] of [[pyrimidine]]s.<ref name="pmid20301396">{{cite book |vauthors=Adam MP, Feldman J, Mirzaa GM, Pagon RA, Wallace SE, Bean LJ, Gripp KW, Amemiya A, Ah Mew N, Simpson KL, Gropman AL, Lanpher BC, Chapman KA, Summar ML |section=Urea Cycle Disorders Overview |veditors=Adam MP, Feldman J, Mirzaa GM, etal |title=Gene Reviews |publisher=University of Washington, Seattle |date=1993 |pmid=20301396}}</ref> |
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==Production== |
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It is produced from [[bicarbonate]], [[ammonia]] (derived from [[amino acids]]), and [[phosphate]] (from [[Adenosine triphosphate|ATP]]).<ref name=":0">{{cite book | vauthors = Bhagavan NV, Ha CE |chapter=Protein and Amino Acid Metabolism |date=2015 |title=Essentials of Medical Biochemistry |edition=Second |pages=227–268| veditors = Bhagavan NV, Ha CE|location=San Diego|publisher=Academic Press|language=en|doi=10.1016/b978-0-12-416687-5.00015-4|isbn=978-0-12-416687-5 }}</ref> The synthesis is catalyzed by the enzyme [[carbamoyl phosphate synthetase]].<ref name=":0" /> This uses three reactions as follows: |
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== Clinical significance == |
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A defect in the CPS I enzyme, and a subsequent deficiency in the production of carbamoyl phosphate has been linked to [[hyperammonemia]] in humans.<ref name="pmid19410549">{{cite journal | vauthors = Nakagawa T, Lomb DJ, Haigis MC, Guarente L | title = SIRT5 Deacetylates carbamoyl phosphate synthetase 1 and regulates the urea cycle | journal = Cell | volume = 137 | issue = 3 | pages = 560–570 | date = May 2009 | pmid = 19410549 | pmc = 2698666 | doi = 10.1016/j.cell.2009.02.026 | name-list-style = vanc }}</ref> |
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* [[Ornithine transcarbamylase]] |
* [[Ornithine transcarbamylase]] |
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*[[Citrulline]] |
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*[[Urea cycle|Urea Cycle]] |
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==References== |
== References == |
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{{reflist}} |
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=== Further reading === |
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{{refbegin}} |
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{{refend}} |
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{{Nucleotide metabolism intermediates}} |
{{Nucleotide metabolism intermediates}} |
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{{Urea cycle}} |
{{Urea cycle}} |
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[[Category:Organophosphates]] |
[[Category:Organophosphates]] |
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[[Category:Carbamates]] |
[[Category:Carbamates]] |
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[[Category:Acid anhydrides]] |
[[Category:Acid anhydrides]] |
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[[Category:Urea cycle]] |
[[Category:Urea cycle]] |
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[[ast:Carbamoil fosfatu]] |
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[[de:Carbamoylphosphat]] |
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[[it:Carbammilfosfato]] |
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[[ja:カルバモイルリン酸]] |
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[[pl:Karbamoilofosforan]] |
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[[pt:Carbamilfosfato]] |
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[[ta:கார்பமோயில் பாஸ்பேட்]] |
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[[zh:氨甲酰磷酸]] |