An amino acid and a product of carbamylation
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Labeled Version(s)
36339Homocitrulline-d3
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Homocitrulline

Item No. 34980

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N6-(aminocarbonyl)-L-lysine
CAS Number
1190-49-4
Synonyms
  • ε-Carbamyllysine
  • L-Epsilon-Amino-Carbamoyl-Lysine
  • L-Homocitrulline
  • NSC 27428
Molecular Formula
C7H15N3O3
Formula Weight
189.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: Slightly solubleDMSO: Slightly solubleEthanol: Slightly solublePBS (pH 7.2): 3 mg/ml
SMILES
OC([C@@H](N)CCCCNC(N)=O)=O
InChi Code
InChI=1S/C7H15N3O3/c8-5(6(11)12)3-1-2-4-10-7(9)13/h5H,1-4,8H2,(H,11,12)(H3,9,10,13)/t5-/m0/s1
InChi Key
XIGSAGMEBXLVJJ-YFKPBYRVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 mg

    $37

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    250 mg

    $82

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    500 mg

    $128

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    1 g

    $181

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    Product Description

    Homocitrulline is an amino acid and a product of carbamylation, a post-translational modification of proteins and amino acids.1,2 It is formed by the adduction of isocyanic acid, a product of urea degradation or thiocyanate oxidation induced by myeloperoxidase (MPO), to the ε-amino group of lysine residues.2 Protein-bound homocitrulline levels are increased in the aortas of transgenic Ldlr-/- mice expressing human MPO fed a high-fat atherogenic diet.3 Intra-articular injection of homocitrulline-containing peptides induce the development of arthritis in mice.4 Homocitrulline-containing peptide and anti-homocitrulline antibody levels are increased in whole blood from patients with erosive rheumatoid arthritis compared to patients with non-erosive rheumatoid arthritis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shi, J., Knevel, R., Suwannalai, P., et al. Autoantibodies recognizing carbamylated proteins are present in sera of patients with rheumatoid arthritis and predict joint damage. Proc. Natl. Acad. Sci. USA 108(42), 17372-17377 (2011).

    2. Verbrugge, F.H., Tang, W.H.W., and Hazen, S.L. Protein carbamylation and cardiovascular disease. Kidney Int. 88(3), 474-478 (2015).

    3. Wang, Z., Nicholls, S.J., Rodriquez, E.R., et al. Protein carbamylation links inflammation, smoking, uremia and atherogenesis. Nat. Med. 13(1), 1176-1184 (2007).

    4. Mydel, P., Wang, Z., Brisslert, M., et al. Carbamylation-dependent activation of T cells: A novel mechanism in the pathogenesis of autoimmune arthritis. J. Immunol. 184(12), 6882-6890 (2010).