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Selenomethionine

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
Selenomethionine: chemical structure
Names
IUPAC name
2-Amino-4-(methylselanyl)butanoic acid
Other names
MSE
Identifiers
  • 3211-76-5 (L) Y
  • 1464-42-2 (D/L) Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:27585 Y
ChemSpider
  • 14375 Y
ECHA InfoCard 100.014.525
  • 15103
UNII
  • 964MRK2PEL (L) Y
  • J9V40V4PKZ (D/L) Y
  • DTXSID7040609
  • 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
  • C[Se]CCC(C(=O)O)N
Properties
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).
N verify (what is YN ?)

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.

Substitution chemistry issues edit

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 cattle, birds, and fish causes alkali disease.[3][4][5]

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).[6] The incorporation of heavy atoms such as selenium helps solve the phase problem in X-ray crystallography.[7]

Dietary intake edit

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.[8] It was determined in a clinical trial that selenomethionine is absorbed 19% better than selenite.[8]

See also edit

References edit

  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.
  3. ^ O'Toole, D.; Raisbeck, M. F. (1995). "Pathology of experimentally induced chronic selenosis (alkali disease) in yearling cattle". Journal of Veterinary Diagnostic Investigation. 7 (3): 364–373. doi:10.1177/104063879500700312. ISSN 1040-6387. PMID 7578453.
  4. ^ Spallholz, Julian E.; Hoffman, David J. (2002). "Selenium toxicity: cause and effects in aquatic birds". Aquatic Toxicology. Amsterdam, Netherlands. 57 (1–2): 27–37. doi:10.1016/S0166-445X(01)00268-5. ISSN 0166-445X. PMID 11879936. S2CID 28251689.
  5. ^ Lemly, A.Dennis (1997). "A Teratogenic Deformity Index for Evaluating Impacts of Selenium on Fish Populations". Ecotoxicology and Environmental Safety. 37 (3): 259–266. doi:10.1006/eesa.1997.1554. ISSN 0147-6513. PMID 9378093.
  6. ^ Hendrickson, W. A. (1999). "Maturation of MAD phasing for the determination of macromolecular structures". Journal of Synchrotron Radiation. 6 (4): 845–851. doi:10.1107/S0909049599007591.
  7. ^ Larsson, A. M. (2009). "Preparation and crystallization of selenomethionine protein". Protein Crystallization. IUL Biotechnology Series. Vol. 8. pp. 135–154.
  8. ^ a b "Product Review: Supplements for Cancer Prevention (Green Tea, Lycopene, and Selenium)". ConsumerLab.com. Retrieved 2008-04-20. Selenium supplements are available in organic and inorganic forms. Some research suggests that the inorganic form, selenite, is harder for the body to absorb than organic forms such as selenomethionine (selenium bound to methionine, an essential amino acid) or high-selenium yeast (which contains selenomethionine). A recent clinical trial found that selenomethionine had 19% better absorption than selenite; absorption from selenium yeast was about 10% better than selenite.

External links edit

  • PDB file for MSE 2018-09-20 at the Wayback Machine
  • PDB entries containing Het Group MSE

selenomethionine, semet, naturally, occurring, amino, acid, selenomethionine, enantiomer, main, form, selenium, found, brazil, nuts, cereal, grains, soybeans, grassland, legumes, while, methylselenocysteine, glutamyl, derivative, major, form, selenium, found, . 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 g 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 Selenomethionine chemical structureNamesIUPAC name 2 Amino 4 methylselanyl butanoic acidOther names MSEIdentifiersCAS Number 3211 76 5 L Y1464 42 2 D L Y3D model JSmol Interactive imageChEBI CHEBI 27585 YChemSpider 14375 YECHA InfoCard 100 014 525PubChem CID 15103UNII 964MRK2PEL L YJ9V40V4PKZ D L YCompTox Dashboard EPA DTXSID7040609InChI InChI 1S C5H11NO2Se c1 9 3 2 4 6 5 7 8 h4H 2 3 6H2 1H3 H 7 8 YKey RJFAYQIBOAGBLC UHFFFAOYSA N YSMILES C Se CCC C O O NPropertiesChemical formula C5H11NO2SeMolar mass 196 106 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 Contents 1 Substitution chemistry issues 2 Dietary intake 3 See also 4 References 5 External linksSubstitution chemistry issues editSelenium 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 cattle birds and fish causes alkali disease 3 4 5 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 6 The incorporation of heavy atoms such as selenium helps solve the phase problem in X ray crystallography 7 Dietary intake editSelenomethionine 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 8 It was determined in a clinical trial that selenomethionine is absorbed 19 better than selenite 8 See also editSelenocysteine another selenium containing amino acid but one that is incorporated into specific locations of specific proteins as directed by the genetic code Selenoprotein Canadian Reference Material of selenomethionineReferences edit 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 g glutamyl derivatives and oxidation products Journal of Agricultural and Food Chemistry 49 1 458 70 doi 10 1021 jf001097b PMID 11305255 O Toole D Raisbeck M F 1995 Pathology of experimentally induced chronic selenosis alkali disease in yearling cattle Journal of Veterinary Diagnostic Investigation 7 3 364 373 doi 10 1177 104063879500700312 ISSN 1040 6387 PMID 7578453 Spallholz Julian E Hoffman David J 2002 Selenium toxicity cause and effects in aquatic birds Aquatic Toxicology Amsterdam Netherlands 57 1 2 27 37 doi 10 1016 S0166 445X 01 00268 5 ISSN 0166 445X PMID 11879936 S2CID 28251689 Lemly A Dennis 1997 A Teratogenic Deformity Index for Evaluating Impacts of Selenium on Fish Populations Ecotoxicology and Environmental Safety 37 3 259 266 doi 10 1006 eesa 1997 1554 ISSN 0147 6513 PMID 9378093 Hendrickson W A 1999 Maturation of MAD phasing for the determination of macromolecular structures Journal of Synchrotron Radiation 6 4 845 851 doi 10 1107 S0909049599007591 Larsson A M 2009 Preparation and crystallization of selenomethionine protein Protein Crystallization IUL Biotechnology Series Vol 8 pp 135 154 a b Product Review Supplements for Cancer Prevention Green Tea Lycopene and Selenium ConsumerLab com Retrieved 2008 04 20 Selenium supplements are available in organic and inorganic forms Some research suggests that the inorganic form selenite is harder for the body to absorb than organic forms such as selenomethionine selenium bound to methionine an essential amino acid or high selenium yeast which contains selenomethionine A recent clinical trial found that selenomethionine had 19 better absorption than selenite absorption from selenium yeast was about 10 better than selenite External links editPDB file for MSE Archived 2018 09 20 at the Wayback Machine PDB entries containing Het Group MSE Retrieved from https en wikipedia org w index php title Selenomethionine amp oldid 1177159992, wikipedia, wiki, book, books, library,

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