Carbamoyl phosphate

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.

Carbamoyl phosphate
Structural formula
Ball-and-stick model
Names
IUPAC name
(Carbamoyloxy)phosphonic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.230.975
KEGG
MeSH Carbamoyl+phosphate
UNII
  • InChI=1S/CH4NO5P/c2-1(3)7-8(4,5)6/h(H2,2,3)(H2,4,5,6)
    Key: FFQKYPRQEYGKAF-UHFFFAOYSA-N
  • C(=O)(N)OP(=O)(O)O
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).
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Infobox references

Production

It is produced from bicarbonate, ammonia (derived from amino acids), and phosphate (from ATP).[1] The synthesis is catalyzed by the enzyme carbamoyl phosphate synthetase.[1] 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
    2    NC(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.[2]

See also

References
  1. Bhagavan, N. V.; Ha, Chung-Eun (2015-01-01), Bhagavan, N. V.; Ha, Chung-Eun (eds.), "Chapter 15 - Protein and Amino Acid Metabolism", Essentials of Medical Biochemistry (Second Edition), San Diego: Academic Press, pp. 227–268, doi:10.1016/b978-0-12-416687-5.00015-4, ISBN 978-0-12-416687-5, retrieved 2020-12-17
  2. Nakagawa, Takashi; Lomb, David J.; Haigis, Marcia C.; Guarente, Leonard (2009-05-01). "SIRT5 Deacetylates Carbamoyl Phosphate Synthetase 1 and Regulates the Urea Cycle". Cell. 137 (3): 560–570. doi:10.1016/j.cell.2009.02.026. ISSN 0092-8674. PMC 2698666. PMID 19410549.

Bibliography
  • Nelson, David L.; Cox, Michael M. (2005). Lehninger Principles of Biochemistry fourth edition. New York: W. H. Freeman and company. ISBN 978-0716743392.
  • "SIRT5 Deacetylates Carbamoyl Phosphate Synthetase 1 and Regulates the Urea Cycle". Cell. 137 (3): 560–570. 2009-05-01. doi:10.1016/j.cell.2009.02.026. ISSN 0092-8674.
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