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Chemical Compound Review:

citrulline (2S)-2-amino-5- (aminocarbonylamino)pentano...

Synonyms: Cytrulline, Sitrulline, Ureidovalerate, L-Cytrulline, L-citrulline, ...

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Disease relevance of citrulline

Reduction in cationicity of MBP, especially due to conversion of positively charged arginine residues to uncharged citrulline (Cit), has been found to be associated with multiple sclerosis (MS) [1].
In rheumatoid arthritis and most non-rheumatoid arthritis rheumatologic disease sera, anti-CCP positivity is citrulline-dependent [2].

High impact information on citrulline

To generate specific hydrogen-bonding interactions with a monoanionic substrate analogue, we have introduced a urea functional group into the active site by replacing arginine side chains with isosteric citrulline (Cit) residues [3].
There was less difference in the ability of the charge isomers, including C8, to aggregate LUVs with a lipid composition resembling that of the cytoplasmic leaflet of myelin (Cyt-LUVs) than for PC/PS LUVs [4].
Because the total number of Cit residues in C-8 from MS and normal MBP is the same, the difference in reactivity may be related to structural factors [5].
CIT recovery in the cerebrospinal fluid and from canine cortical homogenates increased during HCA and reperfusion [6].

Associations of citrulline with other chemical compounds

The plasma citrulline strongly correlated with small bowel length (P < 0.0001) and xylose absorption (P < 0.001) [7].

References

Cryoelectron microscopy of protein-lipid complexes of human myelin basic protein charge isomers differing in degree of citrullination. Beniac, D.R., Wood, D.D., Palaniyar, N., Ottensmeyer, F.P., Moscarello, M.A., Harauz, G. J. Struct. Biol. (2000) [Pubmed]
Anti-cyclic citrullinated peptide positivity in non-rheumatoid arthritis disease samples: citrulline-dependent or not? Vannini, A., Cheung, K., Fusconi, M., Stammen-Vogelzangs, J., Drenth, J.P., Dall'Aglio, A.C., Bianchi, F.B., Bakker-Jonges, L.E., van Venrooij, W.J., Pruijn, G.J., Zendman, A.J. Ann. Rheum. Dis. (2007) [Pubmed]
A designed synthetic analogue of 4-OT is specific for a non-natural substrate. Metanis, N., Keinan, E., Dawson, P.E. J. Am. Chem. Soc. (2005) [Pubmed]
Effect of posttranslational modifications to myelin basic protein on its ability to aggregate acidic lipid vesicles. Boggs, J.M., Yip, P.M., Rangaraj, G., Jo, E. Biochemistry (1997) [Pubmed]
An antibody specific for component 8 of myelin basic protein from normal brain reacts strongly with component 8 from multiple sclerosis brain. McLaurin, J., Hashim, G., Moscarello, M.A. J. Neurochem. (1992) [Pubmed]
Assessing the impact of cerebral injury after cardiac surgery: will determining the mechanism reduce this injury? Baumgartner, W.A., Walinsky, P.L., Salazar, J.D., Tseng, E.E., Brock, M.V., Doty, J.R., Redmond, J.M., Blue, M.E., Goldsborough, M.A., Troncoso, J.C., Johnston, M.V. Ann. Thorac. Surg. (1999) [Pubmed]
Plasma citrulline concentration: a reliable marker of small bowel absorptive capacity independent of intestinal inflammation. Papadia, C., Sherwood, R.A., Kalantzis, C., Wallis, K., Volta, U., Fiorini, E., Forbes, A. Am. J. Gastroenterol. (2007) [Pubmed]

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