Selenomethionine

Names

IUPAC name

2-Amino-4-methylselanyl-butanoic acid

Other names

MSE

Identifiers

CAS Number

3211-76-5 (L)^N
1464-42-2 (D/L)^N

3D model (Jmol)

CHEBI:27585^Y

14375^Y

964MRK2PEL^Y

InChI=1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)^Y

Key: RJFAYQIBOAGBLC-UHFFFAOYSA-N^Y
InChI=1/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)

Key: RJFAYQIBOAGBLC-UHFFFAOYAT

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).

(what is ^YN ?)

Infobox references

Selenomethionine 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.In vivo, selenomethionine is randomly incorporated instead of methionine. Selenomethionine is readily oxidized.

Selenomethionine's antioxidant activity arises from its ability to deplete reactive oxygen species.

Selenium and sulfur are chalcogens that share many chemical properties so the substitution of methionine with selenomethionine may have only a limited effect on protein structure and function. However, the incorporation of selenomethionine into tissue proteins and keratin in horses causes alkali disease.

Alkali disease is characterized by emaciation, loss of hair, deformation and shedding of hooves, loss of vitality, and erosion of the joints of long bones.

Incorporation of selenomethionine into proteins in place of methionine aids the structure elucidation of proteins by X-ray crystallography using single- or multi-wavelength anomalous diffraction (SAD or MAD). The incorporation of heavy atoms such as selenium helps solve the phase problem in X-ray crystallography.

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