Carbamoyl phosphate

Carbamoyl phosphate

Structural formula
Ball-and-stick model
Names
IUPAC name (Carbamoyloxy)phosphonic acid
Identifiers
CAS Number	590-55-6  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17672  N
ChEMBL	ChEMBL369105  N
ChemSpider	272  N
ECHA InfoCard	100.230.975
KEGG	C00169  N
MeSH	Carbamoyl+phosphate
PubChem CID	278
UNII	GC5KZW01Q3  Y
CompTox Dashboard (EPA)	DTXSID70862253
InChI InChI=1S/CH4NO5P/c2-1(3)7-8(4,5)6/h(H2,2,3)(H2,4,5,6) Key: FFQKYPRQEYGKAF-UHFFFAOYSA-N
SMILES C(=O)(N)OP(=O)(O)O
Properties
Chemical formula	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). N  verify  (what is  YN ?) 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

• Ornithine transcarbamylase
• Citrulline
• Mary Ellen Jones (chemist)
• Urea Cycle

References

1. 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.
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.
3. 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.