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'''Ethionine''' is a [[Proteinogenic amino acid|non-proteinogenic]] [[amino acid]] structurally related to [[methionine]], with an [[ethyl group]] in place of the [[methyl group]].
'''Ethionine''' is a [[Proteinogenic amino acid|non-proteinogenic]] [[amino acid]] structurally related to [[methionine]], with an [[ethyl group]] in place of the [[methyl group]].


Ethionine is an antimetabolite and methionine [[Receptor antagonist|antagonist]]. It prevents amino acid incorporation into proteins and interferes with cellular use of [[adenosine triphosphate]] (ATP). Because of these pharmacological effects, ethionine is highly toxic and is a potent carcinogen.<ref>{{cite journal|title=Hypomethylation of DNA in ethionine-fed rats|author=Narayan Shivapurkar, Mary J. Wilson and Lionel A. Poirier |journal=Carcinogensis|volume =5|issue=8|pages=989–992|year=1984|doi=10.1093/carcin/5.8.989|pmid=6744518}}</ref>
Ethionine is an antimetabolite and methionine [[Receptor antagonist|antagonist]]. It prevents amino acid incorporation into proteins and interferes with cellular use of [[adenosine triphosphate]] (ATP). Because of these pharmacological effects, ethionine is highly toxic and is a potent carcinogen.<ref>{{cite journal|title=Hypomethylation of DNA in ethionine-fed rats|author=Narayan Shivapurkar, Mary J. Wilson and Lionel A. Poirier |journal=Carcinogenesis|volume =5|issue=8|pages=989–992|year=1984|doi=10.1093/carcin/5.8.989|pmid=6744518}}</ref>


==References==
==References==

Revision as of 20:17, 13 August 2013

Ethionine
Names
IUPAC name
2-Amino-4-ethylsulfanylbutyric acid
Other names
S-Ethyl-L-homocysteine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.588 Edit this at Wikidata
  • InChI=1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9) checkY
    Key: GGLZPLKKBSSKCX-UHFFFAOYSA-N checkY
  • InChI=1/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)
    Key: GGLZPLKKBSSKCX-UHFFFAOYAB
  • O=C(O)C(N)CCSCC
Properties
C6H13NO2S
Molar mass 163.239 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 checkY☒N ?)

Ethionine is a non-proteinogenic amino acid structurally related to methionine, with an ethyl group in place of the methyl group.

Ethionine is an antimetabolite and methionine antagonist. It prevents amino acid incorporation into proteins and interferes with cellular use of adenosine triphosphate (ATP). Because of these pharmacological effects, ethionine is highly toxic and is a potent carcinogen.[1]

References

  1. ^ Narayan Shivapurkar, Mary J. Wilson and Lionel A. Poirier (1984). "Hypomethylation of DNA in ethionine-fed rats". Carcinogenesis. 5 (8): 989–992. doi:10.1093/carcin/5.8.989. PMID 6744518.