Citrulline
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| Citrulline | |
|---|---|
| Common name | citrulline |
| Systematic name | 2-amino-5-(carbamoyl amino)pentanoic acid |
| Chemical formula | C6H13N3O3 |
| Molecular mass | 175.2 g mol−1 |
| CAS number | 372-75-8 |
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| Disclaimer and references | |
The chemical compound citrulline is an α-amino acid (AA). Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.
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[edit] Synthesis
Citrulline is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family (NOS; EC 1.14.13.39). First arginine is oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with release of nitric oxide.
[edit] Function
Citrulline, while being an amino acid, is not built into proteins during protein synthesis, as it is not coded for by DNA, yet several proteins are known to contain citrulline. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases (PADs), which convert arginine into citrulline in a process called citrullination or deimination. Proteins that normally contain citrulline residues include myelin basic protein (MBP), filaggrin, and several histone proteins, while other proteins, like fibrin and vimentin can get citrullinated during cell death and tissue inflammation.
Patients with rheumatoid arthritis often (at least 80% of them) develop an immune response against proteins containing citrulline. Although the origin of this immune response is not known, detection of antibodies reactive with citrulline containing proteins or peptides is now becoming an important help in the diagnosis of rheumatoid arthritis.
