Ethionine

Ethionine
Names
IUPAC name
2-Amino-4-ethylsulfanylbutyric acid
Other names
S-Ethyl-L-homocysteine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.588 Edit this at Wikidata
UNII
  • 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]

Ethionine has been found to naturally occur in the edible pulp of the durian fruit, and postulated to be a biosynthetic precursor for ethanethiol and other strong odorants found in the fruit.[2]

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.
  2. ^ Nadine S. Fischer and Martin Steinhaus (2020). "Identification of an Important Odorant Precursor in Durian: First Evidence of Ethionine in Plants". Journal of Agricultural and Food Chemistry. 68 (38): 10397–10402. doi:10.1021/acs.jafc.9b07065. PMID 31825619. S2CID 209329891.
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