Selenomethionine

Selenomethionine
Selenomethionine: chemical structure
Names
	IUPAC name 2-Amino-4-(methylselanyl)butanoic acid
	Other names MSE
Identifiers
CAS Number	3211-76-5 (L) ; 1464-42-2 (D/L) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27585 ;
ChemSpider	14375 ;
ECHA InfoCard	100.014.525
PubChem CID	15103;
UNII	964MRK2PEL (L) ; J9V40V4PKZ (D/L) ;
CompTox Dashboard (EPA)	DTXSID7040609 ;
	InChI InChI=1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8) Key: RJFAYQIBOAGBLC-UHFFFAOYSA-N ;
	SMILES C[Se]CCC(C(=O)O)N;
Properties
Chemical formula	C5H11NO2Se
Molar mass	196.106 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Selenomethionine (SeMet) is a naturally occurring amino acid. The L-selenomethionine enantiomer is the main form of selenium found in Brazil nuts, cereal grains, soybeans, and grassland legumes, while Se-methylselenocysteine, or its γ-glutamyl derivative, is the major form of selenium found in Astragalus, Allium, and Brassica species.^[1] In vivo, selenomethionine is randomly incorporated instead of methionine. Selenomethionine is readily oxidized.^[2]

Selenomethionine's antioxidant activity arises from its ability to deplete reactive oxygen species. Selenium and methionine also play separate roles in the formation and recycling of glutathione, a key endogenous antioxidant in many organisms, including humans.

^ Whanger, P. D. (2002). "Selenocompounds in plants and animals and their biological significance". Journal of the American College of Nutrition. 21 (3): 223–32. doi:10.1080/07315724.2002.10719214. PMID 12074249. S2CID 20483595.
^ Block, E.; Birringer, M.; Jiang, W.; Nakahodo, T.; Thompson, H. J.; Toscano, P. J.; Uzar, H.; Zhang, X.; Zhu, Z. (2001). "Allium chemistry: synthesis, natural occurrence, biological activity, and chemistry of Se-alk(en)ylselenocysteines and their γ-glutamyl derivatives and oxidation products". Journal of Agricultural and Food Chemistry. 49 (1): 458–70. doi:10.1021/jf001097b. PMID 11305255.

[1] Whanger, P. D. (2002). "Selenocompounds in plants and animals and their biological significance". Journal of the American College of Nutrition. 21 (3): 223–32. doi:10.1080/07315724.2002.10719214. PMID 12074249. S2CID 20483595.

[2] Block, E.; Birringer, M.; Jiang, W.; Nakahodo, T.; Thompson, H. J.; Toscano, P. J.; Uzar, H.; Zhang, X.; Zhu, Z. (2001). "Allium chemistry: synthesis, natural occurrence, biological activity, and chemistry of Se-alk(en)ylselenocysteines and their γ-glutamyl derivatives and oxidation products". Journal of Agricultural and Food Chemistry. 49 (1): 458–70. doi:10.1021/jf001097b. PMID 11305255.

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