Selenomethionine (SeMet) is a naturally occurring

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...

. The L-selenomethionine

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

is the main form of

selenium Selenium is a chemical element; it has symbol (chemistry), symbol Se and atomic number 34. It has various physical appearances, including a brick-red powder, a vitreous black solid, and a grey metallic-looking form. It seldom occurs in this elem ...

found in Brazil nuts, cereal grains,

soybeans The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source of f ...

, and grassland

legumes Legumes are plants in the pea family Fabaceae (or Leguminosae), or the fruit or seeds of such plants. When used as a dry grain for human consumption, the seeds are also called pulses. Legumes are grown agriculturally, primarily for human consu ...

, while ''Se''-methylselenocysteine, or its γ-glutamyl derivative, is the major form of selenium found in ''

Astragalus Astragalus may refer to: * ''Astragalus'' (plant), a large genus of herbs and small shrubs *Astragalus (bone) The talus (; Latin for ankle or ankle bone; : tali), talus bone, astragalus (), or ankle bone is one of the group of foot bones known ...

'', ''

Allium ''Allium'' is a large genus of monocotyledonous flowering plants with around 1000 accepted species, making ''Allium'' the largest genus in the family Amaryllidaceae and among the largest plant genera in the world. Many of the species are edible, ...

'', and ''

Brassica ''Brassica'' () is a genus of plants in the cabbage and mustard family (Brassicaceae). The members of the genus are informally known as cruciferous vegetables, cabbages, mustard plants, or simply brassicas. Crops from this genus are sometim ...

'' species. ''In vivo'', selenomethionine is randomly incorporated instead of

methionine Methionine (symbol Met or M) () is an essential amino acid in humans. As the precursor of other non-essential amino acids such as cysteine and taurine, versatile compounds such as SAM-e, and the important antioxidant glutathione, methionine play ...

. Selenomethionine is readily oxidized. Selenomethionine's antioxidant activity arises from its ability to deplete

reactive oxygen species In chemistry and biology, reactive oxygen species (ROS) are highly Reactivity (chemistry), reactive chemicals formed from diatomic oxygen (), water, and hydrogen peroxide. Some prominent ROS are hydroperoxide (H2O2), superoxide (O2−), hydroxyl ...

Selenium Selenium is a chemical element; it has symbol (chemistry), symbol Se and atomic number 34. It has various physical appearances, including a brick-red powder, a vitreous black solid, and a grey metallic-looking form. It seldom occurs in this elem ...

and

also play separate roles in the formation and recycling of

glutathione Glutathione (GSH, ) is an organic compound with the chemical formula . It is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources ...

, a key endogenous antioxidant in many organisms, including humans.

In proteins

Selenium and sulfur are

chalcogen The chalcogens (ore forming) ( ) are the chemical elements in group 16 of the periodic table. This group is also known as the oxygen family. Group 16 consists of the elements oxygen (O), sulfur (S), selenium (Se), tellurium (Te), and the rad ...

s that share many chemical properties so the substitution of methionine with selenomethionine may have only a limited effect on protein structure and function. Indeed, bacteria can tolerate a very high amount of substitution of this kind.

Alkali disease

However, the incorporation of selenomethionine into tissue proteins and keratin in cattle, birds, and fish 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.

Structure determination

Incorporation of selenomethionine into proteins in place of

aids the structure elucidation of proteins by

X-ray crystallography X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...

using single- or multi-wavelength anomalous diffraction (SAD or MAD). The incorporation of heavy atoms such as selenium helps solve the

phase problem In physics, the phase problem is the problem of loss of information concerning the phase that can occur when making a physical measurement. The name comes from the field of X-ray crystallography, where the phase problem has to be solved for the de ...

in X-ray crystallography. Incorporation is achieved with the help of a selenomethionine-tolerant microbial expression system: the recombinat DNA for the protein in question is put into a microbe, which is then given large amounts of selenomethionine.

Other biology

Yeast grown under high concentrations of selenomethionine is able to convert selenomethionine into selenocysteine, much like methionine can be converted into cystine. Existence of selenocysteine is enough to trick the cystine-tRNA ligase into producing a tRNA^Cys linked to selenocystine, resulting in the production of non-functional proteins and cytotoxicity.

Dietary intake

As mentioned before, selenomethionine occurs in the human diet. It is one of the main forms of selenium in food along with selenocystine. Selenomethionine is readily available as a dietary supplement. It has been suggested by nutritionists that selenomethionine, as an organic form of selenium, is easier for the human body to absorb than selenite, which is an inorganic form. It was determined in a clinical trial that selenomethionine is absorbed 19% better than selenite.

References

External links

PDB file for MSE
{{Webarchive, url=https://web.archive.org/web/20180920083516/http://xray.bmc.uu.se/hicup/MSE/ , date=2018-09-20

Alpha-Amino acids Selenium(−II) compounds Selenoethers