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| Names | |
|---|---|
| IUPAC name
(Carbamoyloxy)phosphonic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.230.975 |
| KEGG | |
| MeSH | Carbamoyl+phosphate |
PubChem CID |
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| UNII | |
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| Properties | |
| CH2NO5P2− | |
| Molar mass | 141.020 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
Carbamoyl phosphate is an anion of biochemical significance. In land-dwelling animals, it is an intermediary metabolite in nitrogen disposal through the urea cycle and the synthesis of pyrimidines. Its enzymatic counterpart, carbamoyl phosphate synthetase I (CPS I), interacts with a class of molecules called sirtuins, 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.
Classification
Carbamoyl phosphate is a metabolic intermediate in a pathway that involves nitrogen disposal through the urea cycle and the biosynthesis of pyrimidines.[1]
Production
It is produced from bicarbonate, ammonia (derived from amino acids), and phosphate (from ATP).[2] The synthesis is catalyzed by the enzyme carbamoyl phosphate synthetase.[2] This uses three reactions as follows:
- HCO−
3 + ATP → ADP + HO–C(O)–OPO2−
3 (carboxyl phosphate) - HO–C(O)–OPO2−
3 + NH3 + OH− → HPO2−
4 + −O–C(O)NH2 + H2O - −O–C(O)NH2 + ATP → ADP + H
2NC(O)OPO2−
3
Clinical significance
A defect in the CPS I enzyme, and a subsequent deficiency in the production of carbamoyl phosphate has been linked to hyperammonemia in humans.[3]
See also
References
- ↑ 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 (1993). "Urea Cycle Disorders Overview". In Adam MP, Feldman J, Mirzaa GM, et al. (eds.). Gene Reviews. University of Washington, Seattle. PMID 20301396.
- 1 2 Bhagavan NV, Ha CE (2015). "Protein and Amino Acid Metabolism". In Bhagavan NV, Ha CE (eds.). Essentials of Medical Biochemistry (Second ed.). San Diego: Academic Press. pp. 227–268. doi:10.1016/b978-0-12-416687-5.00015-4. ISBN 978-0-12-416687-5.
- ↑ Nakagawa T, Lomb DJ, Haigis MC, Guarente L (May 2009). "SIRT5 Deacetylates carbamoyl phosphate synthetase 1 and regulates the urea cycle". Cell. 137 (3): 560–570. doi:10.1016/j.cell.2009.02.026. PMC 2698666. PMID 19410549.
Further reading
- Nelson DL, Cox MM (2005). Lehninger Principles of Biochemistry fourth edition. New York: W. H. Freeman and company. ISBN 978-0-7167-4339-2.
