Citrulline

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Citrulline
Ball and stick model of zwitterionic citrulline
Names
IUPAC name
2-Amino-5-(carbamoylamino)pentanoic acid[1]
Identifiers
3D model (
JSmol
)
3DMet
1725417, 1725415 D, 1725416 L
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.006.145 Edit this at Wikidata
EC Number
  • 211-012-2
774677 L
IUPHAR/BPS
KEGG
MeSH Citrulline
UNII
  • InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12) ☒N
    Key: RHGKLRLOHDJJDR-UHFFFAOYSA-N ☒N
  • NC(CCCNC(N)=O)C(O)=O
Properties
C6H13N3O3
Molar mass 175.188 g·mol−1
Appearance White crystals
Odor Odourless
log P −1.373
Acidity (pKa) 2.508
Basicity (pKb) 11.489
Thermochemistry
232.80 J K−1 mol−1
254.4 J K−1 mol−1
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

The

Tokyo Imperial University in 1930.[4]
It has the formula H2NC(O)NH(CH2)3CH(NH2)CO2H. It is a key intermediate in the urea cycle, the pathway by which mammals excrete ammonia by converting it into urea. Citrulline is also produced as a byproduct of the enzymatic production of nitric oxide from the amino acid arginine, catalyzed by nitric oxide synthase.[5]

Biosynthesis

Citrulline can be derived from:

Citrulline is made from

trichohyalin at the inner root sheath and medulla of hair follicles, where it is synthesized from arginine.[7] Arginine
is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with release of nitric oxide.

Citrulline is also made by

enterocytes of the small intestine.[2][8]

Function

Citrulline is a metabolic intermediate within the urea cycle, which is the pathway by which mammals excrete ammonia by converting it into urea. Citrulline is also produced as a byproduct of the enzymatic production of nitric oxide from the amino acid arginine, catalyzed by nitric oxide synthase. In the yeast species Saccharomyces cerevisiae, citrulline is a metabolic intermediate in the latter, cytosolic half of the arginine biosynthesis pathway.[9]

Several proteins contain citrulline as a result of a

peptidylarginine deiminases (PADs), which convert arginine into citrulline in a process called citrullination or deimination with the help of calcium ions. Proteins that normally contain citrulline residues include myelin basic protein (MBP), filaggrin, and several histone proteins, whereas other proteins, such as fibrin and vimentin are susceptible to citrullination during cell death and tissue inflammation
.

Circulating citrulline concentration is a biomarker of intestinal functionality.[10][11]

See also

Notes

  1. ^ Early references spell Ryo Odake's name as Ryo Othake.

References

  1. ^ "Citrulline - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 1 May 2012.
  2. ^
    S2CID 88798984
    , retrieved 2020-11-10
  3. PMID 22397107. Archived
    (PDF) from the original on 2022-10-09.
  4. PMID 16746990
    .
  5. ^ "Nos2 - Nitric Oxide Synthase". Uniprot.org. Uniprot Consortium. Retrieved 10 February 2015.
  6. ISBN 978-1-57259-153-0
    . Retrieved 13 March 2020.
  7. PMID 6653155
    .
  8. S2CID 81295089
    , retrieved 2020-11-10
  9. ^ "Saccharomyces cerevisiae citrulline biosynthesis".
  10. PMID 29511548
    .
  11. PMID 11113071
    .
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