Symmetric dimethylarginine

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Symmetric dimethylarginine
Symmetric dimethylarginine.svg
Names
IUPAC name
(2S)-2-amino-5-[(N,N'-dimethylcarbamimidoyl)amino]pentanoic acid
Other names
Nω,Nω'-dimethyl-L-arginine
Identifiers
3D model (JSmol)
973080
ChEBI
ChemSpider
DrugBank
PubChem CID
UNII
  • InChI=1S/C8H18N4O2/c1-10-8(11-2)12-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H,13,14)(H2,10,11,12)/t6-/m0/s1
    Key: HVPFXCBJHIIJGS-LURJTMIESA-N
  • C(C[C@@H](C(=O)O)N)CNC(=NC)NC
Properties
C8H18N4O2
Molar mass 202.258 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Symmetric dimethylarginine (SDMA) is produced during catabolism of proteins. It consists of an arginine core, with one methyl group on each of the two terminal side-chain nitrogen atoms.

Dimethylation of arginine in proteins is mediated by various enzymes, including protein arginine methyltransferase 5 [1] as part of a regulatory pathway of transcription.

SDMA has been explored as a possible biomarker for kidney disease in cats [2] [3] and dogs. [4]

References

  1. ↑ Stopa, Nicole; Krebs, Jocelyn E.; Shechter, David (2015). "The PRMT5 arginine methyltransferase: Many roles in development, cancer and beyond". Cellular and Molecular Life Sciences. 72 (11): 2041–2059. doi:10.1007/s00018-015-1847-9. PMC   4430368 . PMID   25662273.
  2. ↑ Paltrinieri, Saverio; Giraldi, Marco; Prolo, Amanda; Scarpa, Paola; Piseddu, Eleonora; Beccati, Massimo; Graziani, Benedetta; Bo, Stefano (2018). "Serum symmetric dimethylarginine and creatinine in Birman cats compared with cats of other breeds". Journal of Feline Medicine and Surgery. 20 (10): 905–912. doi:10.1177/1098612X17734066. PMC   11129243 . PMID   28994640.
  3. ↑ Braff, J.; Obare, E.; Yerramilli, M.; Elliott, J.; Yerramilli, M. (2014). "Relationship between Serum Symmetric Dimethylarginine Concentration and Glomerular Filtration Rate in Cats". Journal of Veterinary Internal Medicine. 28 (6): 1699–1701. doi:10.1111/jvim.12446. PMC   4895615 . PMID   25272985.
  4. ↑ Nabity, M.B.; Lees, G.E.; Boggess, M.M.; Yerramilli, M.; Obare, E.; Yerramilli, M.; Rakitin, A.; Aguiar, J.; Relford, R. (2015). "Symmetric Dimethylarginine Assay Validation, Stability, and Evaluation as a Marker for the Early Detection of Chronic Kidney Disease in Dogs". Journal of Veterinary Internal Medicine. 29 (4): 1036–1044. doi:10.1111/jvim.12835. PMC   4895368 . PMID   26079532.
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